Women’s Fall Shoe Guide 2019

So this post has been on my mind since August but October seems like just the right time to talk about shoes for fall and winter. If you are like me, shoe shopping is harder than swimsuit shopping. You see I always just get a black onesie, so ya know — one and done on the swimsuit front. But shoes? Shoes are a different story. For one, there are SO MANY OPTIONS out there to sort through from styles to trends to colors and it’s kind of hard to know which ones will be just right for you and your style. Second, it’s hard to know what to do with them once you get them. And third, you want them to last all season long. And I don’t just mean the fall season, I mean through winter, too. I like to buy the shoes I’m going to wear from now until spring right now because right now are the best styles and once this inventory of shoes are gone, I find that the cutest shoes that I was looking for back in the fall are harder to find come December / January.

So for the last few months I’ve been paying attention and making notes of the shoe trend I’ve seen out in the wild and the shoes that I personally love or would love to have. This list ended up becoming this post today, I have a list of 16 shoes for fall — so hopefully there is a shoe for everyone here. I wanted to touch on the classics as well as the trendier shoes with price points spanning from very inexpensive to designer. So below you’ll find my round up of 16 shoes for fall and a breakdown of each style and for some a range of different shoe prices per style.

You’re going to see a lot of the same color ways and hues — this is by design. In my almost 35 years, I’ve learned two things: 1) you are never ready when your avocado is and 2) keep your shoes classic. Besides my vote for a good pair of red heels in your wardrobe, the best shoes in life are black, brown, nude or cream. These hues will get you the absolute most wear out of your closet, tenfold. If you want to waste money on a shoe, my vote is highlighter yellow in patent leather. I know this because I’ve owned this shoe.

Alright, sole sisters — let’s do the damn thing!


1. Everyday Sneaker

I should say this — these shoes are in no particular order. But I do love these sneakers, actually I should say this as well – you can rest assured that I love all of these shoes and if tomorrow I woke up and they were all on my front porch in my size, I would question nothing and no one and happily put them all on my shelf.

Shop The Vans Old Skool Sneaker Here

Back to sneakers! Sneakers have — THANKFULLY — become a staple in the every woman’s wardrobe. A nice white sneaker is always welcome in a closet year round, but I saw these Vans and thought — yep, that’s the exact color of what I want to wear this fall. Brown is in and it is not going anywhere. I like that this color kind of gives these sneakers an elevated look, almost leather like, but they of course are canvas and casual. If you don’t have a great pair of street sneakers — that is sneakers you don’t wear to the gym — pick you up some! Vans are a great place to start, they are trendy, comfortable and well-priced. A few other sneakers are below!

2. Classic Loafer Slide

The ones I’ve featured here are the Gucci slides that I’ve had my eye on for years. (I wrote a post about them last week!) I’ve been wanting them for their classic look and I got them in last weekend and let me tell you — they do not disappoint. The look is classic, pulled together and bit of menswear inspired but they inherently look feminine.  Just a reminder: these are designer, so they have a designer price tag. If you like this look but want a different price, Sam Edelman makes a wonderful dupe that you can find here in a multitude of colors! I’ve linked a few other options below. But overall this shoe an be worn with denim and tops to give you a classic look daily. This shoes specifically fits true to Euro sizing, so I am in the 41 as a US size 10.

Find These Loafers Here

Find a great dupe here!

3. Cognac Heel

This is a heel that I’ve had for a few years and it just keeps giving. This is the Marc Fisher Zala Pump — which comes in many different colors if this one isn’t your jam — but this fall with brown and warm tones being top of the list, you’ll want a cognac option to wear with your warm tones. These specially fit true to size. Finding a good deeper hue pump gives you more options when it comes to changing the look of your classic outfits. This hue gives your outfit a sophisticated and expensive look, especially when paired with a similar hued bag.

Find these heels here!

4. Ivory Bootie

One could argue that an ivory bootie is not an essential but I’d love to be on the other side of that debate with my high school debate team skills ready for opposition. Here is the thing we all know — sweaters last. Good coats last. Fall and winter clothes just last because they are heavier than spring / summer and we tend to buy a nicer quality in the fall and winter. (Especially up north when you NEED those layers to keep you insulated.) So how do you update a sweater look for the new season? Your shoes. Swap out your typical black or brown bootie for a white bootie and you’ll instantly look updated. The rest of your outfit can be from years past but an updated shoe makes a world of difference. This white bootie trend started a few years ago and I’ve followed it for a while before I truly invested in it to make sure it was going to stick around. And you know what? I think it’s here to stay. My one tip: stick with darker neutrals or black hues when working with a lighter shoe. Going ALL light or white will make your outfit look like a costume.

Find These Booties Here!

5. Everyday Booties

Well you should have seen this one coming because I just bragged about finding these booties at Madewell and I absolutely love them. They are the perfect height (for me, you guys know I love a heel) and they are a wonderful shade of brown — not too light and not too dark. I will be taking these boots well into fall and winter with me. I love getting my ‘everyday’ bootie purchase out of the way early on because I know these will be irreplacable this fall.

Find this bootie here!

6. Western Inspired

I know at first glance these black booties don’t exactly scream ‘cowboy’ at you but that’s intentional. Besides I have to be careful, I’m in Texas and when you say ‘Cowboy’ three times  a man on a horse appears and he is really hard to get rid of. But he is helpful when needed to move heavy boxes. Just a quick tip for fellow Texans. The point of this bootie here  is what we are focused on when we say ‘western’ inspired. Some other western inspired boots this fall have leather work on them or just a vague cowboy boot vibe, but having just a little bit more of an interesting take on a black bootie gives your outfit a 2019 flare. This is also a good reminder that you don’t have to take every trend to the Nth degree — western can be done tastefully and with slight. No need to get on your high horse.

Find this bootie here!

7. Basic Bootie

I say basic in the most PSL-loving way: ya basic. And that is okay. Let me tell you something I know deep down in my soul: Uggs are comfortable and they are here to stay. Look by the time January rolls around, you’re going to want a pair of warm but comfortable booties to either wear all day or just as a run to Target. I actually wear mine as mainly house shoes (been wearing the same pair since 2007 if you can believe it! It may be time to upgrade…) but then for the occasional pizza or Target run the Uggs make an appearance and I have to say with a loose cardigan and leggings, I don’t hate the look one bit. It’s casual, it’s cute and it’s basic in the best way. (I prefer the shorter bootie but this classic boot is always a good one! That’s the one I own, but if I were to upgrade say around Christmas time I’d go with this shorter bootie.)

Find this pair of booties here!

Find the classic Ugg here!

8. Knee High / Over the Knee Boots

I don’t see any time in this modern world when we won’t have a love or a need for a knee high or over the knee boot. My advice? If you are under 5’7”, go with a Knee High Boot. If you are over 5’7”, go for either but Over the Knee boots look really nice on tall ladies. I’m working on a full post on how to find the right knee high boots for you but that is my quick tip today. I like this pair from Sam Edelman, they are comfortable, pretty easy to get on (getting them off is a different story though) and the color is classic enough to go with everything. These specific boots are pretty tall for a knee high boot, so if you are more petite these might register as an over the knee boot (in a good way!) They are versatile and can go with dresses or jeans. I’m always a fan of knee high boots not only for the look but for the extra warmth in the winter. Having that extra layer on my shins is a nice plus on a cold, windy day!

Find this pair of booties!

9. Nude Pumps

I don’t think you’ll believe me but I’ve been looking for a good nude pump for YEARS. I had a pair of Kate Spade patent leather nude heels that I wore to death — literally even my shoe guy was like these are trash — and I’ve not ever been able to find an affordable but comfortable pair of nude heels. Are these the one? I’ll have to order them and let you know! But I’m hoping so. (For the record, I kept those Kate Spade heels just in case another shoe guy could work on them.) A nude pump isn’t just for fall though, they are timeless. This shoe works for literally all seasons, so it’s a nice investment to make if you wear heels a lot and you need the perfect, go-with-everything shoe. (Same goes for a nice nude flat, too!) I found this one here and a few below!

10. Printed Booties

Snakeskin is having a huge moment right now in 2019. I mean, move over leopard because snakeskin is taking over. I love this look because (don’t tell Leopard) but snakeskin is actually an easier trend to wear. With a mix of grey, nude and black, snakeskin is the ultimate neutral print and just like the ivory bootie theory, it makes everything pop. You can pair this bootie with literally anything neutral or black and it will look good. It’s the showstopper of your outfit, so let the booties shine.

Find this pair here!

11. Patent Nude Flat

This shoe is menswear inspired but also a nice essential for the everyday. I like the patent leather — which is saying a lot because I don’t love patent leather much — but in this with the soft nude hue it gives the otherwise simple flat some interest. This shoe would work best with dark denim or black pants, but can honestly work with anything. A great neutral is your best defense — you’ve heard that saying right? 😉

Find this Pair of Flats here!

12. Knit Booties

Another of the moment trend I’ve been seeing and loving are these knit booties I’ve seen around town. Designers started this look and I love that it’s a cool mix of fabric and suede, kind of like a sock bootie but much more stylish of course. This look is for the bootie lover but if you are looking for a fancier bootie, like a workwear bootie because it mixes casual with a nice heel. You can pair this with trousers, skinny jeans, pencil skirts, dresses — name it and it works! This type of bootie will give your outfit a classic but trendy look.

Find the booties here!

13. 90s Lace Up Bootie

Look. I know. I know. But hear me out — this lace up booties are coming for you and you just don’t know it yet. I didn’t love them at first either but now I can’t stop putting them in my cart and taking them out. So yes at first I felt a 20 year shiver down my cold millennial spine when I saw that Dr. Martens were trying to make a comeback. This was last fall or so. But now I’m in it — I’m in the late 90s fever dream with all of the Gen Z’ers and it’s not that bad you guys. They actually like puka necklaces and scrunchies, who are we to judge their innocence that we once knew?

Let me tell you though – Doc Martens are comfortable, they are practical and now again they are fashionable. Pair these as you would with any bootie — skinny jeans and a sweater and maybe a thicker sock underneath for good measure. You can dress them up with a floral dress as well, giving grunge 2.0 a real go. I will say this — Dr. Martens are the chunkiest form of this lace up trend, so I’ve linked a few similar here that are a bit more feminine and not so wide / chunky in the sole.

Find This Pair of Docs here!

14. Shearling Winter Boot

This exact boot sold out in a matter of weeks last fall and good ol’ Marc Fisher brought it back to us. Now they are pricey at $250, but if you are looking for a bootie that kind of encompasses it all the trends I’ve listed here — everyday, warm, lace up, shearling — this is your boot. This can be your one and done. I love that the look of what was once a necessity only boot is now a fashion forward bootie. You can dress up your warm winter bootie so that it can be a part of your whole look instead of just your commute, or thinking you have to dress down because you want to stay warm. No ma’am — this look is fashion-forward so keep on being warm and cute at at the same time.

Find this pair here!

15. Ivory Pump

I hope by now you’ve realized that not ALL of these shoes are meant to be bought by one person. No ma’am these are just simply the fall trends I’ve seen and can subscribe to for shoes. So for instance, if you already have your nude heel but are looking for another workhorse of a shoe in your closet, then this ivory pump would be a great addition. This look falls under the same idea as the Ivory Bootie — in fact I would say pick one and go with that look. If you need more work wear shoes, then go with an ivory pump — again this shoe is year round but in the fall / winter you look like a trend-forward bad ass. Pair it with an all black look and let those pumps talk business. I love the unexpectedness of this hue for fall and this Everlane pair is a wonderful option.

16. Clogs

I am one foot in with this trend (lol) only because I love it but I’m not sure if I love it as much as clogs run for these days. You feel me? But this trend is adorable and if you love that Madewell / Everlane look, this trendy shoe is for you. This can be your go-to shoe for fall and winter. Yes I said winter because I know you aren’t going to believe me but it’s fashionable to wear a thicker sock with these. I promise you I’m not pulling your leg on this. I love this black option here because I find that most of my other shoes end up in a cognac hue and giving myself a black option would be a nice shakeup. I mean, if you’re going to shake it up with a clog might as well do it in a classic hue right? But I’ve found a few other options as well if this look is for you! This works with jeans, overalls and long dresses the best! (Found a Madewell pair here!)

Find this pair here!

I hope this post helps you find your favorite shoes this fall / winter!

9 Notes

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  1. Mireia says:

    In love with all these neutral-toned shoes!

    Mireia from TGL
    https://thegoldlipstick.com/

    10.21.19 · Reply
  2. I’m interest about your topic. If you like designing please visit my website.

    10.21.19 · Reply
  3. Eli says:

    In love with the cognac heel! I think I need a pair of those in my wardrobe…
    HAve a great day!!

    Eli

    http://www.curly-style.com

    10.21.19 · Reply
  4. Briana says:

    so love your picks!

    Briana
    https://beyoutifulbrunette.com

    10.21.19 · Reply
  5. vijayan says:

    nice

    10.24.19 · Reply
  6. joe says:

    These are amazing Boots of fall season Thanks you so much!

    10.24.19 · Reply
  7. Rachel says:

    Any plans to do a post about styling cropped pants/cropped flares and booties for fall?!

    10.27.19 · Reply
    • Kendi Everyday says:

      Yes!!

      10.28.19 · Reply
  8. Rob Stark says:

    A nice different collection of shoes

    https://www.ceosuite.com/location/philippines-manila/

    10.28.19 · Reply