1.26.10c{Shop:  Similar Chambray Shirt, Skirt, Boots, Necklace}
I guess I shouldn’t have named this post style “woes” as that seems a bit dramatic. It’s just that I’ve been trying to think of new ways to wear this pretty skirt that I got on the cheap. But it’s surprisingly hard to style. But does that stop me from trying? Ohhhh no. Only velour sweatsuits with words on the butt and fluorescent high-tops stop me. Dead in my tracks.
T-minus two days and I’ll be at Disney World. And I have no idea what to wear. Ask me what to wear to a job interview, I can tell you that. A first date, an engagement party, or heck even prom. But if you ask me what to wear to a giant amusement park in the dead of winter, this is most likely the face you will get:

That’s me grunting/thinking. It’s not pretty when I think, people. I pretty much don’t own anything other than the clothes you see me wear here, so it’s about to get awkward up on this family vacation. And you better believe that I’m going to take outfit photos. I’d have it no other way. 
(Oh wait, I can just style up my velour sweatsuit and high tops. I’ve been waiting for an opportunity to wear those closet gems and here it is. I’m coming for you, Orlando.)

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179 Responses

  1. I grew up in Orlando and no matter how many times I go to Disney, or any theme park for that matter, it never gets any easier to know what to wear! The best news? No one there seems to care or notice! 🙂

    1. Haha I totally know what you mean! No one will care! I think more than anything the shoes have been the hardest for me, as I only have running shoes. And while I don’t mind rocking the shoes, rocking them with skinny jeans is making me cringe…

      1. I think what you need are some chucks or other cute sneakers… maybe it’s just because I’m a SAHM, but I’m a huge fan of comfy, cute shoes.

        1. Agreed! Chucks, Toms, or a classic pair of Keds. They make Keds glittered, zebra print. You name it, girl. I also really love this outfit today. I own a piece similar to everything you have on, and would have NEVER thought to put them together. Adorable.

        2. I wore my TOMS with skinny jeans the last time I went to Disney and was pretty comfortable. Chucks are a good idea too.

  2. kasmira did some great posts on whatiwore2day about what to wear over several days at disney, maybe that would help inspire your packing? good luck and have fun! 🙂

  3. Knowing you, you’ll have the perfect outfits regardless! You’re always so stylin’! Plus, it’s all about fun down there anyway, you could rock a Mickey shirt like nobody else.

    I literally just bought that skirt too. Can’t wait to see how it looks on, as it’s adorable on you! Hoping it looks half as cute!

    1. I’m going to have to rock a Mickey shirt, right? It only feels right that I do.

      I love this skirt — I’m sure it will look great on you! (The waistline is a but weird, but I just belt it and it’s fine.)

  4. I saw that skirt at the Gap and had no idea what to wear with it – but you look super cute and I love it with the brown sweater!

  5. haha:D I enjoy reading your post just as much as admiring your creative outfit combinations. You have an awesome personality :))


  6. We have annual passes so I’m actually going to be there this Friday, too! I love Disney. {If you’d be interested in meeting up, I would love the chance to meet you!}

    My typical Disney (or Universal Studios!) uniform in the winter is a dress with leggings, flat boots and a light jacket. The weather is supposed to be BEAUTIFUL this weekend so I’m sure you’ll have a great time!

    1. You are on to something! I love the idea of navy and white stripes and I have a shirt that would work perfect. Thank you my dear! Are you available for hire? 🙂

  7. Can you believe we don’t have a Gap in this dang town? The only mall in America that doesn’t…grumble. Otherwise, I’d run for that skirt. Love it. And I’ve had my eye on your mustardy brown J. Crew sweater. I think I must buy one. It goes with EVERYthing!!!

  8. jeans and boots would be the best bottoms 🙂 as for tops, anything goes!
    Have super much fun in Disney World! Have more fun than the little kiddies next to you.

    Just Better Together
    come check out my giveaway

  9. I have that skirt too, and I’m so happy to see you style it! It IS a tough one! I wore mine last week with a gray cardi, a blue belt, and some brown boots. And also SUPER jealous that you’re going to DisneyWorld! You should probably just give it up and do some kind of themed attire for the trip (red and white polka dots for Minnie Mouse, seafoam green for Ariel, etc.) And of course get those mouse ears. They’re all the rage.

  10. Way to figure out your style woe 🙂 I LOVE it – I would have never thought to pair olive green+denim with that printed skirt!

    I’ve never been to Orlando in the middle of winter, but Disney World is seriously the happiest place on earth. I really hope a picture in front of Cinderella’s castle materializes!! (And make sure you wear good shoes to walk in – the rides are nothing, but you will walk everywhere :))

    Small Time Style

  11. Hey! You’ll be in my neck of the woods! You’ll do fine if you wear jeans and layers, so if you get too hot, you can shed them. Have fun! Which parks are you going to?


  12. Very jealous of Disney!! I got engaged there! Husband and I may be there next week. <—-weird circumstances. Have fun!

  13. OMG I’m going to be in Orlando this weekend too! I packed jeans, a cute skirt and leggings with some good layers and tanks…but I’m coming from Chicago where it’s 10 degrees..it’s going to be paradise. Enjoy your trip!

  14. Last year when I went to Disney World around Christmas break, it got cold in the evening so, I brought a leather jacket. By fireworks time, it was sooo cold I had to buy a Minnie Mouse hat from the store! (That was fine; I *had* to buy a requisite Disney outfit from Magic Kingdom, didn”t I?) I don’t know the weather in Orlando now, but you’re great at layering so you should do fine with a not-so-Mary Poppins bag to stash your jacket/scarf/hat in. Enjoy!!!

    I love your skirt!

  15. I went to Disney last April for my 10th wedding Anniversary with my kids in tow…yes, I am way much older than you:) Months before our big trip, I laid out every outfit and took photos of the looks including accessories…I am overly obsessed on looking fashionably chic on any trip. Here are my suggestions on what to take on a fun trip to Disney: neutral sandals,one pair of walking shoes which for me were cute flats, skirts, , one fabulous white shirt, blousey tops, stripe shirt, sweater for unusual chilly nights, jeans and a cute dinner outfit. Yes, people may not care what you wear but you will when you see your pictures. You still can look chic at Disney. Have a fun time!

    1. Okay so dinner outfit — what are we talking here? Like a cute dress? I am so on the same page with you. I can’t help but be a bit obsessed whenever I go on a trip. This trip has been haunting me for weeks…

      1. Yes, a cute dress with a cardi for the evening and wedge sandals or even flats if it goes with the outfit. You may even opt for a cute skirt. Weigh your choices and have fun picking your outfits. Again you want to get some fabulous pictures on this trip. Good Luck!

  16. You can wear the same thing you have on now….but without the tights and sub in sandals for your boots. Depending on weather, it’s good to wear something that is long (to protect from sun) but also fairly lightweight so you don’t sweat through it. And make sure what you’re wearing up top keeps the girls in….that is, if you like the roller coasters that tip you upside-down. I hear they frown on wardrobe malfunctions at Disney.

  17. You styled that skirt well. I imagine it with neutral color flats, a grey t shirt, a brown leather/faux leather jacket and a faux fur scarf. Just a random vision that came to me. Have fun in Orlando. If you have time, go to Gator Land to see the animals.

    1. Jo — these visions…do you have them a lot? Can you email them to me? I’m pretty much going to try that outfit you just suggested.

      This is the first I’ve heard of Gator Land, but I’ll try anything once.

  18. I like it. You look pretty

    It’s always hard trying to be stylish and comfortably practical at the same time…

  19. You styled that skirt really well — it’s pretty enough that it would make anything look good, or is that you? Haha… have fun at Disney World!

  20. No. 1 most important thing to pack for Disney: Comfortable walking shoes. Lines are the name of the game at Disney, so be prepared with comfy footwear.
    Light layers are always smart. Orlando is probably warm-ish this time of year, but it’s notorious for impromptu rain showers and thunderstorms. Bring a large umbrella and your preferred rain gear.
    Don’t wear jeans when wandering around Disney. If you get wet from a ride or the rain, they’ll be soggy and heavy and they’ll chafe you.
    I hope this was helpful! Have a wonderful time. 🙂

  21. I like your thinking face! haha. Shoes, comfy shoes. You’ll be standing in lots of long lines. I bet flat boots and a dress could work. Although it can get cool at night, even in Florida!

  22. I would love to see you style velour pants with words on the but and high tops! Somehow it would look chic, I know that!!
    That skirt looks so cute with what you have it with! I always have a hard time styling things cause I want to try stuff with things that people wouldn’t think to put with it. And you do such a good job of that!


  23. I went to Disneyland with my sister, nephew & then 4 month old last year, and I wore knit cotton dresses with cardis, leggings and comfy flats or cute sneakers. Actually my comfy flats are gold birkenstock sandals. They’re cuter than they sound. It was perfect for me and the weather was just sort of chilly but not warm the whole time.

    Also I wore my baby in a tummy carrier the whole time, but that’s an advanced look. 😉

    1. Woahhh I don’t know if I can find a baby in two days, but I’d be willing to try this tummy carrier you talk about. Maybe I can just put snacks in there?

      Your advice is so helpful! But crap — I should have more knit dresses. That’s a really good idea.

      1. Yes, definitely tricky to get a baby without a bit of lead time… I guess you’ll have to improvise. But for god’s sake, this isn’t license to wear a fanny pack.

  24. Wowzers. Absolutely love these color combos! I am inspired to be braver with this skirt.

  25. leggings + flat boots, fitted tunics (flowy stuff is such a pain on rides), cardigans and scarves! and I have a whole ton of faith that I’m going to see that skirt about a thousand more times in a thousand different ways.

  26. You, Kendi of the everyday shop your closet resourcefulness, can’t decide how to style a skirt or dress for a vacation? I don’t believe it. Maybe it was just an off-day, no?

    can I make a Disney attire suggestion? I’m no expert, but I do live in FL and my sisters and I grew up with season passes to the land of the Mouse, so I’ve been throughout the year in all weather. The forecast calls for a lot of sun and temps between 70 and 44 this weekend, so I’d go with thin tights, a skirt or loose shorts, flat boots, and a comfortable top/blouse with a cardigan or button-up over top (I know you’ve got all those things, I just described every bloggers wardrobe). They key will be light layers because while it may be warm outside, the interiors of some of the rides can be cooler. And you’ll be doing a lot of walking, but even more standing around in lines, so you want to be comfortable (hence the boots). Above all, you want to wear something that will look cute in photos but not ruin, wrinkle or constrict. These are the lessons I’ve learned over the years.

    Have fun and keep your eyes peeled for all the hidden mickey mouse ears throughout the parks. They’re in the most random places, it’s amusing.

    1. Not an off day, just an honest day, I suppose!

      Yes, thank you for your suggestion! Always welcome here. And yes, I do have all of those things and yes you did just describe every bloggers wardrobe. Your tips were perfect. Thank you x 100000000.

      Hidden mickey ears? I’ll be on the lookout.

  27. Kendi, please take outfit photos in front of Cinderella’s castle. And with Mickey. Then me living vicariously through you going to Disney will be complete. whereheartmeetssole.blogspot.com

  28. since you basically opened the doors on asking you what to wear to… i have a 2nd date saturday night, what should i wear? it’s FREEZING here in MD, it looks like a very angry shaken snowglobe out my window right now but i’d still like to look cute.
    tell me what to wear & i will totally put the outfit together, as best as i can with what my closet has. BAM.

  29. How is it possible you look so good all the time! I think you should come visit me in Australia and make some sense of m wardrobe … Kendi the traveling muse type thing 🙂

  30. awww disney world! fun!
    i definitely like the brown top with this skirt — i love mixing neutrals!

  31. I live in Orlando! Last time I went to Disney, in December, I wore a cute button-up long sleeved shirt, skinny jeans and Ugg boots. I’d say that but with flats and maybe a light cardigan that you could easily stow away would be perfect. However, I’m no style expert. But I am participating in your 30 challenge, maybe that’ll help? 😉 If you need any advice on what to do, see, eat(etc.) while you’re here, let me know! Enjoy!

  32. I almost bought that skirt, but I didn’t because I didn’t think I could find anything to wear with it! Love how you styled it though.

  33. Kendi–
    Disney World will be so fun. You should try to emulate the various cultures of Epcot’s Around the World. Like while in “France,” posing in front of the faux Eiffel Tower wearing your cute stripes and beret (if you own one). It will no doubt be interesting!

  34. I like 10 minutes from Disney, and I’m there just about every weekend, so I’m there a lot. The forecast has been for the sixties this week, but its been pretty warm. I’ve been wearing shorts and tank tops all week. It rained earlier this week, so I would bring an umbrella and extra socks. If you go on a water ride or get stuck in the rain, the absolute worst thing is chafed toes 🙂

  35. Ha! I love that photo of you thinking. And can’t wait to see what you wear at Disney. We were there last year and had a blast, but I don’t usually wear tennis shoes so I didn’t know how to style them. I got blisters after my first day in flip flops.

    1. Oh no! Indiana (Adored Austin) advised me on footwear as well. I will be sure to wear comfy shoes!

      (I don’t ever wear tennis shoes, but I got some for this trip. I feel like a total hipster in my skinny jeans and new kicks. It’s kind of hillarious)

  36. I bought this skirt in black and white and am having the same trouble styling it. Just this morning I put it on, couldn’t figure out how to wear it and chose something else. This gives me some ideas though…thanks!

  37. first, thanks for you super cute blog. my new years resolution was to start dressing and styling better. i’m a school teacher and the ol khakis were being far too overworn! so, that’s how i found your blog. it’s very inspiring!

    second, i am from florida….but live in Virginia now.

    third, we just got back from disney! my resolution was in full force, so i had to make sure i was dressin up even when i would have rather been schlepin.

    so, here’s my secret to you…..shoes! it’s really alllll about the shoes! find your single most comfortable pair and style around the shoes. because at the end of the day…it’s going to be all about the feet!

    after that..layer. a tank, a t shirt (classic white always works), and then a nice long cardi. i wore mine with boyfriend jeans, rolled up and my most comfy flats. added a super cute belt and long necklace…and viola! not only was i super comfy, i took the sweater on and off throughout the day and even ended up in just the tank at one point. it was perfect!
    just thought i would share….because i know the fashion dilemma you face!
    have fun!!

    1. Stephanie

      Wow! Thanks for the comment and advice! Okay I was thinking that shoes were the most important, as I get cranky when my feet hurt. I have some tennis shoes that I think will work. I like your outfit suggestions, too! I but you looked adorable all day long. Did you see other people dressed as cute as you or did you feel over dressed?

      (Yes, I know it’s weird that I’m literally obsessing over this….)

  38. I LOVE this outfit! Everything about it is perfect. Have a blast at disneyworld! I haven’t been since I was a kiddo. I would recommend capris and comfy blouses.

  39. yay! I will let you in on all my spots to go shopping/thrifting in Orlando… Welcome! OK, wear cute comfy flat shoes with jeans or boots with leggings…srsly, its the ultimate Theme park outfit. It’s chilly down here 🙂

    Have fun drinking around the world at Epcot (Japan is my fav)

    1. Chilly? I can do chilly! Except for on the water rides, I probably will not be partaking in chilly wet rides.

      I WILL have fun drinking around the world. 😉

  40. Hmm, I’m going to advise you not to wear your boots. I’ve actually WORKED at an amusement park before and trust me, your feet will need some kind of support when you’re standing and walking all day. I would go with a sleek fashion sneaker like this one that I actually own:http://www.kaboodle.com/reviews/customer-rating-review-1399 paired with leggings and a slouchy top. Take loose cardi to wear when the weather cools down. Oh and if it’s really cold you can layer a long sleeve tee/thermal underneath the slouchy top. Hope that helps!

    1. Lidi — thank you for the advice! I was wondering about boots…I mean I do have Uggs (shhhh) but I probably won’t wear my Steve Maddens, since they have little to no support. I love your suggestions. I have little tennis shoes like that, so I will definitely take them.

      Your advice helped a lot! Thank you!

      1. Glad I could help! It sounds like it might be a bit cool down there so you might actually want to double up on the leggings (I tend to overact to cold weather, I’m such a wienie!) or maybe trade them out for some of those super comfy Gap skinny jeans? Those seem comfy and stylish, a winning combo!

        And I have Uggs too (our little blogger secret!) but seriously, how can I NOT have them, they’re like outdoor slippers, so cozy!

  41. It’s actually been kind of chilly this week & I think it will be in the high 60s this weekend. I would have to say the most important thing are the shoes you take! I wear either my Toms, Keds, or Van-like slip ons…. I wouldn’t wear flats (boy have I done that before! eek) although comfy boots might be ok.

    Yay for Disney!!! Have fun!! : ]

    P.S. I’ve never commented before but you are one among my favorite bloggers! Thank you for being so diligent & inspiring!!

    1. Laura! HI — thanks for commenting and reading, you sweet thing you.

      Okay, so Toms would be okay? I was wondering if they would be. I think that I will throw them in just in case. My suitcase is going to be ridiculously huge. hehe.

  42. Coming from someone who actually used to WORK in entertainment at WDW, I can promise you that just from this post I’ve decided- no matter what you wear, you will be the most stylish one there. No joke. You may need to take your smelling salts- many velour suits with high tops will be seen. haha! jk. But for realls, you’ll be so cute no matter what. It may be kind of on the “colder” side. So don’t plan on summer clothes.

    I just found your blog and love it. 🙂 I’d love if you have time to check mine out. gentrilee.blogspot.com

    1. Gentrilee — Oh thank you! How fun that you worked there. So smelling salts are in order…that many velour suits, huh?

      I will not plan on summer clothes, although I wish I could. Summer casual is so much easier than winter casual.

      1. haha! think spring. You can wear lighter clothes, just make sure to have a jacket with you. Someone mentioned an umbrella, that’s a must. Also, I think skirts/ dresses are great to wear to Disney. They’re what I always wear. You’ll feel cute, plus they dry really fast from the water rides. Just make sure you tuck it under your legs before the ride begins. haha!

  43. I don’t know if any of your flats have good support (and the ability to stay attached on crazy rides?), but you might be able to make some of them better for standing in line with gel inserts. I’d recommend leggings/cotton dress/ cardi (can be smooshed in bag without wrinkling) combo or skinny jeans with a classy, but non-fussy shirt- add scarfs wherever necessary.

  44. OMG! Disney world is my favorite amusement park! I’ve been there so many times before that I should be over it already but once I step in the park I’m like a little girl again! Can’t wait to see pictures, no matter if you wear velour pants with huge messages on the back, I wanna see! Have fun doll!


  45. I would wear comfortable shoes, like a cute pair of keds. Probably jeans, or pants. You don’t want a skirt flying about in the wind on a roller coaster. They may arrest you for that. Make sure you bring lots of layers, and a waterproof jacket, or a little umbrella. It rains a lot in Florida. The worst thing is if it’s cold there, and you didn’t bring anything warm to wear. I had that happen, and ended up buying a very ugly super overpriced zip-up hoodie. Believe me you don’t want that to happen.
    My Heart Blogged

  46. Yeah I definitely wouldn’t have called this post Style Woes. I’d call it Style Win!

    I absolutely love it!

    Good luck at Disney World. I suggest frilly ankle socks and something with ears.

    1. Style Win! I love it. 🙂

      Haha — I’m sure I’ll end up with the Ears by the end of my trip. My MIL is crazy like that.

    1. You know, I had a hard time deciding between the black/white and navy/red – – mainly because I wanted both. Haha, but I think the black/white will be easy to style. If anything you can always just add a white blouse, right?

      Now that I think about it, I can just do that too…hmmm…

  47. I can’t wait to see your vacation photos. Have FUN! Disney World is one of my favorite places ever. Maybe you can give us some tips on what to wear once you figure it out.

    1. IF I figure out what to wear, you know I’ll hand them over gladly.

      I’m so excited — I’ve only been to Disney Land when I was twelve and I’ve heard that WDW is way better. Either way, I can’t wait!

  48. Loving the colors and I can totally see why the skirt would be challanging but you did great.
    So for Disney parks, you will feel best if you are wearing some sort of disney themed top of some sort. They have amazing styles (at very expansive) prices. My fave are tinkerbell tee but done in a distressed kind of way and very nice fitting. I also own a mickey rock and roll zip up hoodie. If F21 still has those minnie tee’s that would be great too. Can’t wait to see what you will end up wearing. Have fun.

  49. so I wanted to give you some ideas on other ways to style your skirt. Since you felt you had trouble with styling it, I’m visual and I tried to see other ways you could style it/pattern it with.

    I was thinking you could style it with a blouse/top with tiny polka dots…. um, the complimentary color to red is green. Red and green too christmasy but if you put it with like an olive green/army green vintage tshirt and a jean jacket. I’ve actually drawn out the color wheel to see what colors could go together for an outfit. (actually not 100% sure if I’ve done it for an outfit but I have in my life to see what colors go together/or compliment.) It’s really late and I’m tired! Google “color wheel” it’s cool to see what colors can meld. Maybe you’ve already done that. ciao! enough from me already 😉

    1. Oh I like your ideas! YOu know I do have a polka dot top, I wonder if that would work? I can always try!

      And yes, I can totally see army green with this skirt. I could do that easily! And no I’ve never googled color wheel, but I’m about to…

      Thank you for the sweet tips, Marie.

  50. we went to wdw in january a few years ago and it’s not that cold. i think shoes is the most important…having something comfortable and a couple options is key. i think it’s easily shorts weather but i’m from oregon so 65 felt amazing compared to the 40 degrees i was coming from. i’m sure you’ll look cute no matter what.
    p.s. you can’t help but want to wear disney stuff. a little while back f21 had some cute minnie mouse shirts, i would totally see if they still have some and buy a few…you can’t not wear disney after like the first day there.

  51. Comfy shoes and light layers are absolutely key. The mornings might start off chilly, but the Florida sun might make you break a sweat as the day progresses. And be sure to pack an umbrella! It always seems to rain at least one day every time I go. Better to be safe than sorry!

    Other than that, enjoy the cool weather and smaller crowds! I’m travelling there this summer with my family for my niece’s golden birthday on July 4, so it will be hot and crowded. I’m still excited, though!


  52. Should you ever decide to jump ship and teach English at a junior high school in rural Japan, you're velour tracksuit and high tops will help you fit in with all of the other teachers. Just something to keep in mind when you're drawing up the 'ol five year plan.

  53. Have fun babe! I’m sure it’s gonna be tons of fun and you’ll find the perfect thing to wear! 🙂


    P.S: I’m having an “I {heart} MY BLOG” tote giveaway! I bet you’d like it! 😀

  54. I'm from orlando and just went to Disney for my birthday. Winter is my favorite time to go to the theme parks. I always wear jeans, comfortable flats, basic tee and cute layers depending on the temp. Also, a messanger bag like purse is a must (trust me) You will be comfy and look great in all of the photos!

  55. the velour & high tops are probably pretty spot on for what you’re gonna see other people wearing – so you’ll probably fit right in! hehe
    If you wanna go the extra mile i’ve got a bambi character sweater you’re welcome to 🙂

  56. I’ve never been to Florida in my life! This is exciting, you’ll have so much fun. I can’t wait to see the photos!

  57. Everybody will be wearing jeans, jackets and tennis shoes. Have fun!

    – Meredith

  58. add a phanny pack to your orlando outfit and you are go to go. and throw in a visor…if you are feeling fancy.

  59. Kendi that is so exciting that you are coming to Orlando!! I live in Orlando and when I was a child my family went every year! Now that I am older, I can’t afford to do that! The weather is going to be in the 70’s and I just heard this morning that there will be rain on Thursday/Friday(maybe). With the sun that we usually have, even when it is in the 60’s, it can feel nice and warm. Are you coming here just to go to Disney??

    1. Yes! We are coming just to go to Disney with my hub’s family. I checked the weather and it does look like it’s going to be super pretty. I can’t wait!

  60. So I’m helping my cousin’s daughter find something to wear to prom. Since you mentioned it…. what should she wear? 🙂

    1. Hahaha — I did mention that, didn’t I? Let me look into what’s cool for high school kids. Is it short or long this year?

      If I were your cousin’s daughter, I’d go sparkly. Sequins seems to be the hot thing right now. She could also go with classic black and NOT regret her prom dress many years later…

  61. I went to Disney World a few months ago and I would say pack comfy shoes first and foremost. Second, for packing my line of reasoning was can I ride a bike in this outfit? Because that is the kind of mobility you need and with all the attractions you’ll probably want some coverage. I hope you have a blast and I can’t wait to see what outfits you come up with!


    My little profile picture is me rocking some sequin Minnie ears from that trip!

  62. i live in the land of the mickey. sooo, jeans, comfy shoes, tshirt and a hoodie. that’s all you need. since you’re married no need to look super hot. and mickey is taken too, so save your energy for rides, large turkey legs and ways to get around strollers 🙂

    how long you going to be in orlando for!?

    1. Jamie! I think that I will wear that exact outfit you described! So jeans are okay? I’m getting a 50/50 response on jeans. Of course, that’s all I own so….

      I will watch out for those strollers…

      It’s just a quick family vacation, so Friday through Monday (I think)!

      1. Jeans are absolutely appropriate. And layers, and comfy shoes (it’s amazing how many miles you can walk at Disney). A cute windbreaker/raincoat for the random Florida showers would be good too.

        And bring a water bottle (save you $$$$$).

        Get a Dole Whip in adventureland (AMAZING – pineapple soft serve ice cream).

  63. I have that same skirt in black and white– the easiest color combo in theory– and I have problems styling it. The white just looks so harsh. Maybe I will attempt an ovedeye on it…

    But anyways…
    You pulled it off. Good outfit!

    1. Kasmira —

      I actually read your post last night! You gave some great tips — I had no idea it was even open at night. (I’m an idiot?) I don’t know if I can look as cute as you did, but I’ll try!

  64. Comfy shoes are a MUST. You will probably end up doing more walking than you could ever imagine there! Also, gets cool in the mornings and evenings, but warms up in the day. So go for light layers- a t-shirt or tank top with a light hoodie or jacket, and a pair of jeans. As it warms up, you can lose the jacket and cuff the jeans into capris.
    Your first day there, go to the Disney Village. There’s a store there called TrenD. They have the cutest Disney themed clothing and accessories on the property! Get a few different things to wear throughout your trip there.
    Have fun! 🙂

  65. Hey, I live in Orlando! I think you’re gonna love it! So for Disney, it’s all about comfort. Period. I’ve been there trying to look cute and end up regretting it. By the end of the day everyone looks tired and crappy so it doesn’t matter, lol! I have found that flip-flops are suprisingly more comfortable than sneakers. I don’t know if you’re a flip-flop girl, but here in Orlando, you see it even through out winter. Either way I always take a pair of sneakers in my backpack. Backpacks! That’s another thing! I always leave my purse at home and take a backpack with essentials from my purse, a sweater, and sneakers. You’re probably gonna need an umbrella too cause pop-up storms are super common here, unless you just want to buy the infamous Disney Poncho… It’s been rainy lately too. Oh but back to clothes, this skirt (http://oldnavy.gap.com/browse/product.do?cid=41724&vid=3&pid=809741&scid=809741022) is the most comfortable thing I own and I love wearing it to Disney World. But cotton and jeans is a great way to go! Layers also! Cause the day starts off cool, but warms up to about 75 by mid day and then back to cool. Anyway, sorry to bombard you with info, but I hope I helped!

    PS… shopping in Orlando is AMAZING… We have a huge outlet mall and Zara… if you’ve never been to Zara… GO!!

    1. Sweet girl — THANK YOU for the tips. You did not bombard me at all. I appreciate it everything you said!

      Okay, the poncho. That’s brilliant. I’m writing that down right now. So jeans are okay? I figured since it was Jan, that was the way to go but some people said no jeans? But that’s most likely what I’ll wear.

      I will definitely bring some flip-flips as well. Good idea!

      1. No problem! And your readers are right.. you see some of the CUH-RAZIEST outfits at Disney. I take pics when they’re not looking. 😉 It’s like that website People of Walmart..lol! Its insane. And I’ve seen girls in heels. HEELS! Just crazy to me. Anyway, I’m sure whatever you wear will be fine cause you are adorable and have such an awesome fashion sense, the I bet even your loungewear is fabulous! 😉

  66. I have that skirt too and I always love it when you wear it because it gives me ideas of how to style it!

  67. first let me say; I love this outfit. none of it “matches” but it so goes! 🙂 second; I worked at Disney World last winter and so I know what the majority of people wear while in the parks and around town. I would definitely bring jeans and pants. You might get away with longer shorts, depending on the weather, but bring a sweater or two. As with any theme park, sneakers are a smart choice for happy feet. Oh, and don’t forget the most stylish of all accessories at Disney; your mouse ears! 🙂 Have a magical trip!

  68. as i’ve told you before i have this skirt also & never know how to style it either! i don’t wear a lot of red so i felt lost. however i love that you matched it with the brown and chambray. a bit of an unorthodox combo, but it totally works.

    i recently purchased a white sweater with red bretton stripes and a couple buttons down 1 shoulder. i wore that tucked in to the skirt, and it worked pretty well. the unexpected stripe-square combo left people saying, “say what!” (not really.)

    good luck with disney. i have the same problem when it comes to amusement parks, as i think most people wear gym sneakers to those kinds of places and the idea of that is just unthinkable for me. just as unthinkable as matching sweatsuits.


  69. Think about Disney like being pregnant… follow me on this.
    1) your back and feet hurt,
    2) no matter how put together you look at the end of the day you’ll feel like someone kicked your insides,
    3) you have to pee all of a sudden and can’t find a bathroom,
    4) all you want are comfortable clothes and shoes,
    5) you get a glow – but it’s from sun exposure plus sweat,
    6) jewelrey and scarves are your best friends for making you look cute.

  70. Never fear: you’ve done an excellent job at styling this outfit. In fact, it’s one of my favorites–the colors go really well together.

    Also, please don’t worry about what you look like while you’re in Disney. No one else does. Trust me on this. If you were, in fact, wearing a velour sweatsuit and neon hi-tops, you’d fit right in. I was, frankly, floored when I arrived in April, decked out in a sundress and a straw hat, and was quickly surrounded by a sea of fanny packs, sweatshirts, and jorts with Tinkerbell on the butt.

    But, really, you’ll look cute no matter what. I’m sure of it!

  71. Awesome combo you got goin on here! I almost bought that skirt but wasn’t sure how to remix it. You, clearly, are a remix guru and this is only one bit of evidence of that.

    I was just at Disney in November. A few tips:

    1. You’ll be the best dressed one there. No, really, the things people wear there are really appalling.
    2. Comfy shoes! I cannot stress this. It’s so much more walking than you could ever anticipate.
    3. It’ll be cold at night, bring something warm you can carry all day with you.
    4. Dresses are appropriate (I wasn’t sure but ended up wearing them a lot down there). I just wouldn’t recommend any up-side-down rides.
    5. When in doubt, look to your Princesses for inspiration (aka blue chiffon and a tiara).
    Have fun!!

  72. I live in Florida and grew up about an hour away from Disney, so I feel qualified to offer Disney fashion advice. Here it is:

    Wear comfortable shoes.

    This is my only advice. They can (and should!) be cute comfortable shoes, but you’re going to be walking and standing around a LOT and you will hate yourself by last parade if you don’t take comfortable shoes seriously for this.

    The other tourists will have left all their fashion sense at home, so as long as you don’t wear a poorly fitting Disney t-shirt or pants with writing on the butt, you’ll be the cutest one there. Jeans are fine (I always wear jeans when I go in the winter), and layers are a good idea because winter days in Florida start freezing and end up 75 degrees. Rain gear is a good idea too, as it rains a lot here. Disney umbrellas/ponchos are expensive and usually neon, so bring your own. (Okay, so comfortable shoes wasn’t my only piece of advice, but it was the most important!)

    February is a great time to visit Disney; it’s one of the least crowded months. They actually do Florida resident discount packages this time of year to try to draw locals into the park. I’ve been a billion times and I still love it – I’m sure y’all will too!

  73. Wear comfortable shoes. I don’t understand the moms who push strollers through Disney while wearing four-inch heels.

  74. i have that skirt too and was afraid that it would be hard to match when i bought it, but it was such a good deal i couldn’t resist. your photo has given me hope 🙂

  75. never fear! i consider myself a dress-for-disney expert. i’m officially in L-O-V-E with disneyland and go whenever humanly possible. if you want some suggestions i’d be more than happy to send them your way! i’m sure you have a million suggestions already but if you want you can email me at saltcitystyle at gmail dot com. 🙂

  76. Ok, I just wrote out a huge novel and dang Disqus deleted it when I logged in, grr.

    I took my itty bitties last summer and style is everywhere from athletic gear to dresses and sandals. That was disney LAND but I think the style is pretty universal.

    My ideal disney outfit was

    – closed toe shoes that my feet were already used to (for me that was Toms)
    – rolled up boyfriend jeans
    – floral (flowy-ish) tank
    – cardigan that would survive getting rolled up in my bag when it got too hot
    – small cross body bag (I had a 5 month old last time we went so I had to do a back pack)

    Hope that helps!

  77. Oh and whatever you do – DON’T do those lame ass bride and groom minnie/mickey ear hats. I know you and Bryan will be very tempted, but try to resist the urge. So many levels of shame there…

  78. I live about 45 mins from Disney World and though everyone has already said comfortable shoes, that can’t be stressed enough. Your feet will hurt as much as your cheeks (from smiling of course) by the end of the day.

    And it’s been warm/cold/warm/cold here, so layer in case it’s 40-ish in the AM and 70+ in the afternoon. Jeans are good, but make sure they’re stretchy or you’ll be uncomfortable on rides. And be prepared to get a little wet on Splash Mountain, the seats are ALWAYS wet, so keep that in mind if you chose to wear jeans. It sounds silly but I usually carry a folded paper towel in my back pocket to wipe the Splash Mountain seat!

    emilybk is completely right, you will be appalled at how people dress at FL amusement parks. 98% of them are not Floridians, so please don’t let that influence your idea of FL style (if there is such a thing). Don’t worry too much about being fashionable, be more concerned with comfort.

    Disney is supposed to be the happiest place on earth, but people watch when you are there – I love to count how many people actually look happy – it’s usually like 10. Parents with small children usually look the most miserable. It’s really hilarious. And be prepared for lines! Get your fast pass at rides like Space Mountain and Splash Mountain and come back at the scheduled time. Trust me, it’s better than a 2 hour wait. Have fun in Orlando!! And get a giant turkey leg, they are not to be missed.

  79. You may be having trouble with this skirt, but it doesn’t show. This is such a great outfit! I love the colors, the proportions, the layers, everything! It’s so adorable!!!!

  80. Hi Kendi!
    I’ve been reading your blog for a couple months now and I love it! This is the first time I’m commenting(hence why it’s so formal). I have this same skirt in the black and white color (I just wore it yesterday!) and seeing the way you styled this one previously inspired me to be more creative with it. Sometimes I wear a shirt tucked into it, sometimes with a vest, and usually with fun-colored tights. The way you styled it today is wonderful. You’ve quickly become one of my fashion idols. Thanks for being awesome!

  81. Kendi. I’ve lived in Orlando my whole life. Let me tell you right now that if you were to wear velour pants with “PINK” written on your tush, high top sneakers, and a baggie white T shirt with a hoodie, you’ll fit right in. hahaha.

    Honestly, every time I go to disney, I wear comfy, stretchy jeans (LOVE YOU JEGGINGS), cute ballet flats or sneakers, and in winter, I’d probably just wear what you’ve got on right there….a button down with a sweater over it. Oh, and if you have a crossbody bag, that’s the way to go, too.

    Don’t stress. It’s Orlando. Land of “I love Florida” t-shirts that are 5 for $25 with palm trees and flamingos on it.

  82. I know the feeling of the “tricky but cheap so you want to wear it a lot” skirt. I have one (er maybe a few) that I love in theory but like less in practice.

    Good luck on your vacation!

  83. I really love this skirt and I really love how you styled it here and really think I may have made an almost identical comment the last time you wore it. Because I really love it.

    As for Disney World, I suggest red with white polka dots. Yellow Keds. And…jeans? That’s what I have planned for Disney LAND next month, anyway. When in doubt, consult Minnie.

  84. I have been reading your blog for a while and I’m taking a trip to Austin, what are some good stores to look at while i’m there?

  85. Hah! I totally bought that skirt, loved the print (and price!!) only to get it home and hit a brick wall too! Why oh why is it so hard to style? It’s cute, it should go with other cute things, non? I love how you styled it though- I’ll definitely try mixing it with more colours now (it’s been stuck paired with blacks, whites and greys). xx

  86. It’s not really TERRIBLY dead of winter here. It’s low 60s to low 70s (I live about 45 min from Disney), and perfect for pretty much anything you want as long as you pack a warm sweater and maybe a light scarf if you plan on being outdoors for the night shows. I would also wear comfortable shoes (maybe flat boots?) because of all the walking. I’m sure you’ll be comfortable and stylish! 😉

  87. Just a quick FYI. I’m from Colo. Went to Disney World a couple of years ago in late Dec., definately colder than I would have expected. Make sure to bring lots to layer up. I found the mornings and late evenings to be suprisingly chilly. I wore jeans, tees, cardigans, and jackets and shed/put-on layers more often than not. A lightweight wool layer, ala featherweight merino, goes a long way.

  88. Okay, I’m no help on the Disney issue, but I am loving that skirt. Can I ask a personal question? How tall are you? They don’t have it in stores here any more but I’m 5’9″ and don’t want to bother if it’s going to look like a cheerleader skirt on me. Love your blog!

  89. I have those same boots! Love the look, and love your blog!

    I started a design and style blog a few months ago… I’d love for you to check it out!

    Allie 🙂

  90. Holla! You’re coming to my neck of the woods. Except I don’t work at the “D Word”. I work at that other beast, Universal. That’s so exciting! A little advice, when you go to Disney, eat at Primetime Cafe in Hollywood Studios. It’s built to look like a 1950’s kitchen and your waitress is your “mother” and makes you eat all your vegetables. It’s totally brilliant. And it’s pretty nice in Orlando right now. I’m a firm believe in the magic of a light dress, sweater, and tights. And maybe a light little peacoat for good measure 🙂 Have a good time!

  91. I like the way this worked out, something about the green sweater combined with the skirt that is pretty awesome!

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