50 Ways to Wear a Dress

Gap (different color)
 or similar | Flats: Target | Bracelet: c/o Oia Jules}
The worst and best part of a style blog is the constant question of “what else can I do with this piece of clothing?” It’s best because it makes you think, it forces you to be creative which then leads to outfits you had never thought of before. It’s worst because well for me anyways I feel like I constantly have to wear something different. Somedays I can’t just wear a maxi dress — instead I must make it awesome! amazing! best idea ever!
But today I just wanted to wear a maxi dress and try my 90’s-licious vest with it. (As I’m headed to the Peach Pit for lunch. And if you don’t get that reference I can’t even look at it.) Is this awesome, amazing, the best idea ever? Probably not, but I like it. And that’s good enough for me. 
Forgive me — the title of this post was misleading at best. I only have about three other ways to wear a maxi dress, so with the vest that makes about 4. Only missing 46 other ways. I’ll get on that soon. 
Other ways to wear a maxi: With a scarf, with a blazer and all alone.  

129 Notes

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  1. Asilia says:

    This look is awesome. Love the combination of the denim with the kind-of-fancy dress. 
    And I am awaiting the 46 other ways.

    06.19.12 · Reply
  2. Carrie says:

    I have that question in my head all the time because I don’t go shopping all the time.
    Love the dress though =)

    Style in the City

    06.19.12 · Reply
  3. such a beautiful maxi! i really like this background!
    ~ http://www.Tinacious.Me

    06.19.12 · Reply
  4. I have that dress too! And also did an outfit post on it today! Brain wave…

    Love the denim vest combo!


    06.19.12 · Reply
  5. Amy @ Leopard and Lillies.com says:

    Love the Peach Pit reference.  Like the vest with maxi.

    xx Amy


    06.19.12 · Reply
  6. Jess says:

    i feel the exact same way about my maxi dresses too …. they are just so comfortable that I have to always find new ways … love it with the denim vest!!!

    06.19.12 · Reply
  7. Mia says:

    I’m very new to style blogging and I’m already finding that out 🙂 Especially when I get a new clothing item and all I want to do is wear it over and over. 


    06.19.12 · Reply
  8. elizabeth says:

    i love this dress and i love it even more with the awesome vest! 

    06.19.12 · Reply
  9. Natali Karppinen says:

    You look flawless in this maxi dress! 


    06.19.12 · Reply
  10. Love all 4 of your ways.  4 ways is actually pretty impressive!!

    06.19.12 · Reply
  11. I used to want to go to the Peach Pit. Sit at the booth in the corner and drink a milkshake. Oh how I miss you 90s.  http://www.stephaniewriteshere.com

    06.19.12 · Reply
  12. The Adored Life says:

    Hey! 4 ways is a pretty dang impressive number so don’t knock it!


    06.19.12 · Reply
  13. Freya @ from Freya, with love says:

    I love maxi dresses and am so pleased to see you got your from Gap!


    06.19.12 · Reply
  14. Typhanie says:

    I love maxi dresses! I feature quite a few on my blog. Thanks for the vest idea! 🙂


    06.19.12 · Reply
  15. Carlee says:

    I love that denim vest and I am also a huge fan of maxi dresses. Love this look so clean and casual.


    06.19.12 · Reply
  16. marina miouprincess says:

    love the colour of your dress and the combo with the tan sandals! xo

    06.19.12 · Reply
  17. Jupe_Cambria says:

    That teal is so pretty…and is perfect with the awesome 90s denim!

    <3 Cambria

    06.19.12 · Reply
  18. Em says:

    Cool dress but awesome wall!  Love that wall. 

    06.19.12 · Reply
  19. Kimberly says:

    This might be the coolest wall ever that you chose for your backdrop – and this color looks divine on you! 🙂

    06.19.12 · Reply
  20. KK @BSMMH says:

    Totally agree with you, Kendi…I think what I used to love about dresses is that you could just throw them on and go, and now that I fashion blog, dresses are my biggest conundrum because I feel like I’ve got to make them exciting. I think your vest makes the dress plenty exciting (so does your Peach Pit reference), so kudos to you! Love the look…can’t wait to see the 46 other ways haha. =)


    06.19.12 · Reply
  21. It looks perfect with the vest

    06.19.12 · Reply
  22. ShoeAxis says:

    I’m actually featuring the Moss approach maxi dress from Bloom tomorrow on my blog. I hope I do it justice…it was so hot that day and my husband is doing his best with photography.

    06.19.12 · Reply
  23. Give Nat my best!

    06.19.12 · Reply
  24. Abbey says:

    As much as I try to wear denim jackets and vests again, I can’t. My extremely ugly and gawky preteen days are forever seared into my memory, and it includes the most hideous, oversized denim jacket known to man. However, I am really liking this vest to mix up a maxi. You’ve inspired me to overcome my denim fears.

    Along Abbey Road

    06.19.12 · Reply
  25. Andrea says:

    OMG!! I love your Peach Pit reference because that’s all I can think about when I think of the Denim Vest! I lived in mine in the 90s, my college years, and I have a hard time thinking of making the investment!

    06.19.12 · Reply
  26. aliya says:

    I love the combination of dresses with denim vests!  And the combo looks amazing on you!

    x Aliya

    06.19.12 · Reply
  27. Amanda says:

    i say ‘brilliant!’

    06.19.12 · Reply
  28. love that maxi!

    Xo Megan

    06.19.12 · Reply
  29. Haha, you always make me laugh Kendi! Love the peach pit reference. Your title actually reminded me of the Paul Simon song, 50 Ways to Leave Your Lover.  And actually he only gave about 4-5 ways too.  Love your 4 ways of wearing a maxi dress, you look pretty as always! 🙂

    xo, Yi-chia

    06.19.12 · Reply
  30. Bahaha, I totally forgot about the Peach Pit.  Anyway, I love every time you wear this gorgeous dress, and whenever you repeat any item regardless if it’s done in the most amazing way or not, for that matter.  That’s one of my favorite things about your blog!

    06.19.12 · Reply
  31. Kara M says:

    LOVE the Peach Pit reference! You could also carry around your massive cell phone to be really cool!

    06.19.12 · Reply
  32. Andrea says:

    I like the dress with the vest. It looks very realxed, perfect for a day spent in the sun. 🙂
    xo Andrea

    06.19.12 · Reply
  33. emily says:

    I just bought those Target shoes after seeing them in another one of your posts! They are so comfy and I love their cognac-ish color.

    06.19.12 · Reply
  34. Sparkle says:

    that dress is gorgeous 🙂


    06.19.12 · Reply
  35. Betina, Styled Our Way says:

    I simply love your writing. I think it is a pity that we constantly look for something “new” when it comes to fashion. – using what you’ve already got is so much more clever.

    06.19.12 · Reply
  36. Elissa says:

    you must feel so much pressure to always reinvent the wheel – but i have to say sometimes simplicity is best and i certainly love this look just as much as any crazy imaginative way of wearing a maxi dress!

    06.19.12 · Reply
  37. your 90’s-licious vest is divine! i’m craving a denim vest but haven’t come across a cute one that’s affordable yet!

    06.19.12 · Reply
  38. phiphi says:

    gorgeous!! i love that you are using what you have in new ways – may this be an inspiration to us all to shop our own closets more often!! xox P


    06.19.12 · Reply
  39. Tiffany says:

    Love the colors and how you paired it with your 90’s-licious jean jacket 😉  I also am really digging that wall!

    06.19.12 · Reply
  40. You’re a sneaky one Kendi! Nice post title. 😉

    06.19.12 · Reply
  41. I like to add scarves or belts to mine.  But mostly scarves.


    06.19.12 · Reply
  42. Give Kelly and Donna my best!

    06.19.12 · Reply
  43. Kat says:

    I think this is an awesome idea! I constantly think about that too. I try to be as practical as possible when I purchase things… and think of how else I can style or pair the item.


    06.19.12 · Reply
  44. silviali says:

    I love the vest! I’ve been looking for a denim vest, instead of a jacket. This summer’s going to be way too hot for jackets. 

    06.19.12 · Reply
  45. Tracie says:

    So are you going to go surfing with Brandon and Dylan this summer?? I had to call Old Navy for a denim vest. Im getting stuck in the 80’s jamming to Def Leppard sooooo yeah.

    06.19.12 · Reply
  46. Kristian says:

    Hm, I definitely feel that way about clothes sometimes. The outfit I posted about today was really simple- “Is it really blog-worthy?” but then again…. in summer you don’t want layers and simplicity can look gorgeous as you do here. 

    06.19.12 · Reply
  47. Chaz says:

    Gawd, I used to watch 90210 every week in high school to get ideas on what I should wear to school! They were so cool and dreamy… (love the outfit, BTW)

    06.19.12 · Reply
  48. SO cute! Love your point about how fashion blogging encourages is to think creatively. Very true!


    06.19.12 · Reply
  49. Karen says:

    Donna Martin graduates! 🙂 Cute dress!

    06.19.12 · Reply
  50. Yes! I agree…Ill plan my look for the day and think it looks great and then realize that it needs that extra something to make it post worthy! I love your vest, Ive been looking all over for a good one. Ive even considered buying a jacket and cutting off the sleeves!

    06.19.12 · Reply
    • Tracie says:

      Old Navy has some really cute ones right now.

      06.19.12 · Reply
  51. lillypea says:

    Oddly enough, I’ve found myself thinking about 90210 a few times today.

    06.19.12 · Reply
  52. Andrea Jardine says:

    4 ways is pretty good! I’d like to see somebody wear any type of dress 50 different ways. challenge!

    06.19.12 · Reply
  53. If anyone could find another 46 ways it would be you. I love the look with your denim.

    x x

    06.19.12 · Reply
  54. Lexi says:

    Gosh, that dress is a really beautiful colour. Love a good maxi, too 🙂

    06.19.12 · Reply
  55. Whitney says:

    Great color! Maxi dresses are a girl’s best friend! 


    06.19.12 · Reply
  56. Genie says:

    Lol, thanks for the misleading title, I can’t wait for the 46 other ways! The color of the dress is amazing, and I really like how you made it more casual with a denim vest. 



    06.19.12 · Reply
  57. Pip says:

    It is such an easy solution to add a vest over a dress that you have no clue what to wear with anymore!  I love the look!  


    06.19.12 · Reply
  58. Mannie Surcam says:

    Stunning!!!!I could see myself wearing that

    06.19.12 · Reply
  59. Love this! That dress makes the denim vest look chic!

    06.19.12 · Reply
  60. Mrs. Baker says:

    haha i think it looks great!


    06.19.12 · Reply
  61. Luciemint says:

    Beautiful look! Romantic and chick at the same time! Great job!
    You have an amazing blog)

    06.19.12 · Reply
  62. I recently found a maxi dress and I am excited to wear it different ways. I avoided them before because I was short, but now I can’t wait to find more! Check out how I wore it on my blog!


    06.19.12 · Reply
  63. Zadin says:

    Funny post! I really believed you there for a second!

    I’m a leopard, new post  

    06.19.12 · Reply
  64. onyxsta says:

    I like the colour of this dress on your skin. Teal is such an odd colour on mine…well, that shade wouldn’t work for me anyway 🙁


    06.19.12 · Reply
  65. Mz Savvy Style says:

    Love your maxi! As a fellow style blogger I feel your pain! I’m afraid to leave the house in just a “plain old outfit” in fear I will disappoint people! Occupational hazard! 😉

    06.19.12 · Reply
  66. Anita says:

    As I don’t have any maxi dress, I can wait a bit for the other 46 ways to wear it 😉 I love how you combined it with this vest, such a retro style! 
    May I help you a bit (I’m not at all such a great blogger as you, but I have some ideas and perhaps you’ll like some of them): 
    – with a knotted chambray shirt or a knotted white blouse? 
    – with a white blazer (or do you count blazer in general as one possibility to wear it? Then it will be definitely difficult!), a black blazer (black is not the same as navy !),
    – with tights and something brown/autumn appropriate for autumn
    – with a cardigan over it to make it look like a maxi skirt
    – with a bouclé jacket and pearl jewellery to make it look “retro and classy”
    – with other blue/green colors to make it an “underwater maxidress-outfit” 
    Okay, enough… I hope I could help you a bit!
    (But I already think you are a pro in wearing everyday something different, I’m so glad I focus on what to wear to concerts and the opera on my blog, so that I can repeat my day-time-outfits at least!)

    xxx Anita

    06.19.12 · Reply
  67. Rachael Hawkins says:

    Love it with the vest but love the Peach Pit reference even more!!  I’m not gonna lie- I got super excited when I read ’50 ways to wear a dress’!  But understand that’s quite a feat to come up with 50 ways! Such a pretty dress on you!

    06.19.12 · Reply
  68. Iliyana Licheva says:

    lovely! I really like it!


    06.19.12 · Reply
  69. Rebecca says:

    LOVE the title…and since I’m totally addicted to maxi dresses right now, I need the 46 other ways. :). Here’s a few to add to your list…add a cardigan, a loose tank, a longer sleeveless vest, a blouse (belted or not), or a denim jacket. And feel free to post pics of those looks so I can get the nerve to wear them myself. 🙂

    06.19.12 · Reply
  70. Courtney says:

    I know what you mean! Sometimes I just want to wear the same outfit twice, it was a good outfit, doesn’t it deserve another run? O the blogging world the good and bad it brings. 

    06.19.12 · Reply
  71. Jessica Broyles says:

    I love it!! I don’t think that most my outfits are “best idea ever” outfits… but they’re cute and make me happy! You’re right, that you like it is enough. 🙂


    06.19.12 · Reply
  72. Maja says:

    This outfit is perfect for the Peach Pit! You look great. I love the colour of this dress and have been trying to find this vest at a thrift store for ever…. may have to cave and pay full price for a new one.

    Maja – http://clotheskinksandcurls.blogspot.ca

    06.19.12 · Reply
  73. I love this outfit! A great way to remix my maxi dress.



    06.19.12 · Reply
  74. Mica says:

    Love the vest with the maxi dress. Maxi dresses are so pretty on their own, they rarely need much remixing! 🙂


    06.19.12 · Reply
  75. Zaira msu says:

    me encanta 🙂
    un beso


    06.19.12 · Reply
  76. Kacie's Kloset says:

    I just got a vest last week and love it! You looks great!


    06.19.12 · Reply
  77. Fearsandfancies.blogspot.com says:

    Dude, you will make Dylan McKay swoon! But watch out for the wrath of Kelly and Brenda.

    06.19.12 · Reply
  78. Natalyascloset says:

    I love your outfit! You’re such a doll :). http://www.natalyascloset.com/

    06.19.12 · Reply
  79. kendrarose says:

    Cute dress!!



    06.19.12 · Reply
  80. Marimar Mat says:

    Love the denim vest! And I can easily imagine how great it would look at Peach pit! So cool!


    06.19.12 · Reply
  81. Kate says:

    I love the outfit. Personally, I like it when style bloggers repeat outfits but change up the accessories, it makes them seem more like real people and less like a magazine. 

    06.19.12 · Reply
  82. Bit says:

    We had very similar Outfits today! You pictures are much better though 🙂 Love the color of your dress.

    A Little Bit

    06.19.12 · Reply
  83. Elena says:

    Love color of your dress! Amazing pictures!!


    06.19.12 · Reply
  84. Bfeor032 says:
    06.19.12 · Reply
  85. Lindsay says:

    Love the Old Navy vest! I got the jean jacket in the light denim, but thinking about going back for the vest

    Lindsay @ LindsayJEveryday.blogspot.com

    06.19.12 · Reply
  86. Crystin says:

    I stopped buying a ton of stuff and started trying to rework what I had. It led me to a ton of new ideas! Love that vest!


    06.19.12 · Reply
  87. Joyce says:

    Love the vest with the dress!


    06.19.12 · Reply
  88. simple is fabulous! besides with the hot weather we’re lucky we can pull together fashionable, innovative and breathable outfits girl

    06.19.12 · Reply
  89. Abbie Darling says:

    Not only do I love your chic, creative style, but your posts are always perfect! You seriously have fun with everything you write and wear– inspiring! 

    06.19.12 · Reply
  90. Amy B. says:

    cute look

    06.19.12 · Reply
  91. Adedoyin Adetoba says:

    That is so funny. My blog today was maxi in 2 ways with a vest and with a belt. Check it out I gave you another way.


    06.19.12 · Reply
  92. Paula says:

    You are so right! great tips and you look beautiful in this maxi dress!


    06.19.12 · Reply
  93. Houndstooth & High Heels says:

    Knot it or throw a chambray button up over it (buttoned and tied) to turn the dress into a skirt! I love coming up with innovative ways to wear the same piece over and over!

    Great post!


    xo, S

    06.19.12 · Reply
  94. rhodawong says:

    i love your maxi dress! it is the perfect fit! i should head to gap and search for this one!


    06.19.12 · Reply
  95. Taylor Laree says:

    I love it. The dress is soft & pretty but the vest really edges it up. 


    06.19.12 · Reply
  96. Amy Campbell says:

    Amazing Peach Pit reference. 90210 is on Netflix. Seriously amazing to re-watch so many years later. I enjoy!

    06.19.12 · Reply
  97. TheresaTran says:

    LOVE the denim vest with the maxi dress!! Very cute!


    06.19.12 · Reply
  98. I often wear my maxis as skirts with a tee or sweater over them..so onlu 45 more ways left 🙂

    06.20.12 · Reply
  99. Meredith says:

    Thank you so much for being fashionable AND affordable! I hate when my favorite bloggers wear $300 cardigans and $800 dresses. I fall in love with their clothes and then could never afford them! Thanks for showing us how to style on a budget!

    06.19.12 · Reply
  100. Sweetsoflife86 says:

    Pretty dress. Love the color
    xo, Petra

    take a look on my newest Outfit Post with a pretty Giveaway

    06.20.12 · Reply
  101. Sweet Harvest Moon says:


    06.20.12 · Reply
  102. Cassandra says:

    Already an amazing post even though its not completed! Love the color of the dress.


    06.20.12 · Reply
  103. I have been singing the praises of the jean vest all summer. I have the exact same Old Navy one and it’s been my favorite item of clothing for the past three months.

    06.20.12 · Reply
  104. Missy says:

    You could wear a shirt over the dress and make it look like a skirt…

    06.20.12 · Reply
  105. Kristin says:

    Cargo jacket, denim jacket, wide belt, cargo vest, chambray shirt, loose off the shoulder tee, cardigan, a tank knotted in the front…the list goes on and on! 🙂

    06.20.12 · Reply
  106. Jenny says:

    I think I need to try out the jean vest, I love the way you styled it with the maxi 🙂

    Seize the Styles

    06.20.12 · Reply
  107. This color is great on you.  I love how you provided the other ways you’ve styled this dress.

    06.20.12 · Reply
  108. Sarah says:

    I’m quite familiar with the “how can I wear this again and again but never in the same way” conundrum. Maybe you should wear this dress everyday for a week (or 50 days – just go for it – but maybe wash it a couple times) and wow us with your versatility.


    06.20.12 · Reply
  109. Caroline L. says:

    Lovely outfit… I’ve been so into denim lately, but wouldn’t have thought to pair this with a denim vest- Great thinking!

    06.20.12 · Reply
  110. Doan says:

    The denim vest suits well with the maxi dress.  I constantly am faced with the problem of trying to figure out what I do with a piece of clothing. Some are winners, some aren’t but that’s the beauty of it! It’s like being a mad scientist in fashion. Love it. 

    06.20.12 · Reply
  111. GiovannaPacini says:

    Loving the denim vest! I’m obsessed with vests right now! Plus your outfit is totally Peach Pit worthy! lol

    http://www.oliveandanarrow.comTreena Bean Giveaway!

    06.20.12 · Reply
  112. Heidi says:

    I love my maxi dresses and hate putting them away in the winter, so I throw a pull-over sweater on top. In the summer I love putting a t-shirt on top with a belt and tie a knot at the bottom. Changes the look and makes it breezier! -Heidi

    06.20.12 · Reply
  113. Seekingstyleblog says:

    Ooh, I was tricked! But I still enjoyed the post of course 🙂

    xo Jennifer


    06.20.12 · Reply
  114. Love that green color!

    06.20.12 · Reply
  115. GingerPurple says:

    Artful Vision is seeking new artists  – made in US. http://www.artfulvision.com

    06.21.12 · Reply
  116. Michaella says:

    I love this dress! I have a similar one but in black 🙂 Perfect for the summer!

    Quite A Looker

    06.21.12 · Reply
  117. chillairandperfume says:

    You can totally pull of this 90s-grunge look, Kendi! I love the vest on you. I’ve been contemplating buying one of my own, but I haven’t pulled the trigger yet.




    06.21.12 · Reply
  118. Lovecardelia says:

    Love maxi dresses! Really love this color and with the denim 😉


    06.21.12 · Reply
  119. jesscuellar says:

    a maxi dress is one of the best pieces to maximize a wardrobe. i love to layer mine with a turtleneck, boots and belt in the winter.

    06.21.12 · Reply
  120. Bit says:

    I mentioned this post in my most recent outfit post 🙂 I was overwhelmed that I managed to wear something so similar to what you were wearing on the same day! Now, I must be doing something right. 

    A Little Bit

    06.21.12 · Reply
  121. Kristen says:

    Love it! I had the dilemma of what to wear with my maxi this morning and I ended up with a sweater, but I like the denim vest better!


    06.21.12 · Reply
  122. april says:

    a. I love the jean jacket maxi dress combo
    b. the sandals are just smash’n
    c. the wall in these pictures is so cool! 



    06.21.12 · Reply
  123. Mihaela P. says:

    I love the color!
    And I got the reference :))….90s rule!

    06.22.12 · Reply
  124. yce says:

    Sorry! i think im the only one missing this out.. 50 ways? why can i only see a single outfit? please help! 

    06.22.12 · Reply
    • Kendi Lea says:

      The 50 ways was tongue and cheek, as I mentioned in the post. I did link to a few other ways to how I’ve worn it before but that’s why I said I have quite a few more outfits to go if I was going to come up with more ways. Always read my post with a heavy dose of sarcasm 😉

      06.25.12 · Reply
  125. Ali says:

    I got the Peach Pit reference, Kendi.

    Brenda Walsh wannabe

    06.22.12 · Reply
  126. RedTagChicLosAngeles says:

    I love maxidresses a lot…..& it’s the most versatile piece we can accessorize ever!


    06.24.12 · Reply
  127. Megan says:

    I see a baby bump?????????

    06.25.12 · Reply