One of the most requested posts is back — what shoes for fall to buy this year! On a whim last year while shoe shopping for myself I thought ‘dang, I wish there was a guide out there that could just pick the shoes I need for fall for me.’ Then I realized that you would like this as well and I should make that guide for you! Well, if we are being honest, for me as well. So this year, I started my deep dive into this years trends by googling ‘fall shoes 2020’ and I came up with a lot of high fashion results. A lot of ‘what’s on the runway’ or ‘new styles to wear for 2020’ and to be honest, none of that is helpful. But because of that one scene in Devil Wears Prada where Miranda Priestly absolutely manhandles Andi’s pride in front of the entire team about the trickle down effect of high fashion to consumer trends, I now know that the trends set by high street fashion does affect the trends we buy (eventually.) Therefore I will not shame talk designer fashion. But I also know that high fashion and everyday style are two very different things, so this guide is for everyday style and even more drilled down to 2020’s changed landscape. This is the most interrupted year for fashion, especially for shoes, so a lot of the trends I’m seeing are way more casual than past fall trends. I hear a collective sigh from the back. We see you, fellow flats lover and we salute you. This is your year.

I’ve edited this post a bit from last year, giving just three options per style. The first one is my preferred option or pick, but keeping different budgets in mind the following options will be similar looks but different price points. I don’t want to overwhelm you with choices, so I picked the best three from different price points I could find!

How to shop this post:

One note: I am not suggesting you need 16 new pairs of shoes this fall. Unless you’ve been in the market for 16 new pairs, that is. 😉 Instead use this guide to help narrow down the shoe or shoes you really want or need. If you’ve been thinking about a new pair of boots, find the trend that works best for you. For example, if you are more casual and like to wear mainly tops and denim, an ankle bootie will be perfect for your closet. If you are more trendy, try a lace up bootie or a lug sole boot this fall. This is to help guide you to find your perfect fit for you. And if you’d like to reference this for later in the season, be sure to pin this post so you can find it later!

Shoes for Fall

(use the {+} to go directly to each product)

 1 / Ankle Bootie

I didn’t mean to ‘rank’ the shoes by order but I will say that this is probably my first choice for a bootie this fall. The ankle bootie is a classic and has been for years and I’ll tell you why: they go with everything. Denim, dresses, leggings (not yoga, Ponte). Dressed up top or just a tee, they can make any outfit work. If you’ve not invested in an ankle bootie yet but you’re looking for a great everyday boot, look no further! Swipe through above to see my three picks, each one a different price point and retailer.

Shop the Vince Camuto bootie here.

2 / Nude Flat

This is one that I would say is on the year round list, but it’s definitely a nice one to have for fall. I’ve been leaning on my flats a ton this year, as they are the best option to feel put together when running errands etc, and you don’t want to go full atheleisure or AKA my couch to Costco outfit. I love a pointed flat, but this square toe option from Vince has been my choice as of lately. Swipe through for other options!

Shop the Vince Flat here.

3 / Neutral Heel

If this one feels like a ‘read the room’ kind of suggestion, I hear you. I am not suggesting you stomp around your house with heels on (unless it makes you feel powerful and chic and then by all means!), but in case you were looking for a pair of heels this fall I wanted to have an option for you. Everyone else, skip to #4.

For fall a nice neutral, tan heel is where it is at this year. A warm neutral can go with so many outfits and can especially warm up a denim ensemble. Think of this heel as the laid back version of classic black pump. With a warmer neutral, you can pair it with any autumn hues this fall. I love this heel I’ve featured above that is almost half mule / half pump and features an acrylic strap to give some interest. Oh the places I would go in those heels. Lucky for me, my commute from the bedroom to the living room is heel-friendly and no one cares if I take them off after 11 am.

Shop the Schutz pump here.

4 / Cap Toe Flat

I’ve been loving the idea of a cap toe heel or flat for fall and winter. For this fall especially, the cap toe flat can be your everyday look. This style is a classic and timeless look, one that can dress up a simple denim and sweater outfit this fall. Originally made popular by Chanel, this style has been reimagined a few times and I love this pair here; an almost identical look to the classic Chanel Ballerinas.

Shop the David Tate Cap Toe Flat here.

5 / High Heeled Bootie

I love this sleek style of bootie. This look is perfect for the women who loves an all black, chic ensemble. It’s a sexy shoe, let’s not deny it. Basically the winter equivalent to a high heeled pump. In fact, you can pair almost the same things that you would black pumps with these high heeled booties, they are that sleek and chic. (Sans a power suit. A power suit needs heels. I don’t make the rules, ok?) If you are more prone to wearing all black and love a more sleek look, this is your bootie. Pair it with black everything all winter long.

Shop the Marc Fisher Oshay Booties here.

Knit Madewell dress with black chelsea boots and Tory Burch Leather Backpack.

6 / Hiker Boots

I love that hiking boots have made a full on fashion statement in the last few years. And I would love it even more if I lived up north, because let’s be honest we aren’t getting too cold down here. This hiking boot trend is very Madewell-esque, think tomboy style with a touch of feminine. This look is best worn with tall socks bunch around the ankle with skinny jeans and lots of layers up top. If I was a New Yorker, this would be my winter shoe of choice for certain. It gives off that cool girl vibe that I pretend I have 😉

Shop Marc Fisher Izzie Boots here.

7 / Snakeskin Booties

Last year I picked up my first pair of snakeskin booties, which I was hesitant to at first because I wanted to make sure it was something that I’d wear and not just a trend I hopped on. (Remember when my sweet two year old called them Dino Boots?? The cutest thing ever.) So after having them for a full fall / winter season, I can say this: they are occasional booties for me but I really like having them as an option. They work best with a monochromatic outfit — think all black with a pop of snakeskin. Or they work with classic pieces, like a white button down and denim to give you outfit a pop. Here is why I like them, not so much for fall but for the dead of winter: they give the sweaters you’ve had on repeat for weeks a new life. Switch out your booties and change your whole look.


Snakeskin booties are for those of you who are looking for a new twist on a basic shoe. If you want a pop of pattern, a little bit of bold, then this bootie is for you.

Shop the Marc Fisher Yale Bootie here.


8 / Slip On Mules

One more flat for the list, this notched flat mule is such a great style for fall and a great everyday shoe. If you find your outfits lean more to darker neutrals, a black mule would work perfect for you. I love the slide on aspect of a mule, not only for comfort but for convenience. The pointed toe gives this shoe a more polished look, so I would definitely suggest keeping a pointed or square toe for the slip on mule. You can also find a few styles with the chain across, which is huge this year. Either way, a black slip on mule is the way to go for fall.

Shop the Emilia Flat here.

9 / Over the Knee Boots

I’ve loved an over the knee boot for years now but I have to admit: I never want them until I want them. Does that make sense? Like buying them in early fall always seems so trite, but that first cold snap hits and it’s all I want to wear. My favorite way to style them is with a dress, a mini dress especially, which is a nice way to bring seasonal dresses into the fall. But in deep winter, pulling them over skinny jeans as another layer of warmth is such a nice and chic way to stay warm. The good news is OTK boots come in all different widths, sizes, heights and budgets! So if these three aren’t your favorite, there are SO many great ones out there. Start at Nordstrom first and then branch out to other retailers. I always find Nordstrom has the best selection / most sizes.

Shop the Marc Fisher OTK Boots here. 

10 / Lace Up Booties

Now this one I have 5 options because I wanted to include black leather options as well. The lace up bootie has a few different variations — you can go military, vintage or street. So I’ve included a few different styles above.

I love this style for fall and this is another great option for an everyday bootie. If you want a more trend forward everyday bootie instead of the standard ankle bootie, this is your gal. I love this shoes layered with tall socks with dresses or denim, it’s gives you outfit a really cool, almost vintage vibe. This style does take a bit more of a bolder step, so keep that in mind. This look is on my list this year to try out again, since you know I wore this style into the ground in high school! The 90s are here, baby and they are here to stay.

I love this Madewell version, but you can never go wrong with a classic Dr Martens 1460 Pascal boot as well.

Shop the Madewell Lace Up Booties here.

11 / Fur Lined Booties

Ah, the Ugg boot. Look, if there was ever a year that made a case for the glorified house slipper that’s acceptable out in public, it’s this year. This is a shoe I own but I don’t wear a lot of on here, but perhaps I should. Mental note: wear more Uggs on the blog. I have a pair that I bought — get this — in 2007. And they are STILL good. That’s incredible, no? I want a short ankle pair because those are little cuties and I’v been waiting for mine to give out but…these boots last. The ankle bootie is so right now and so easy to wear. I personally love it best with leggings and an oversized sweater, but you can wear this bootie truly any way you want. There are no rules with Uggs.

Shop the Ugg boot here.

12 / Lug Sole Boot

This is another 90s throwback style that’s been updated and I’m a huge fun. I love a chunky sole / heel on a boot because it creates visual interest and gives a bit of lift without feeling too heavy or too heeled. So what’s a lug sole?  Think Timberlands, that thick rubber sole with deep indentations and now you’ve got a lug sole boot in mind. I love this style; it feels like a juxtaposition between a workers boot and a feminine bootie. I have these lighter suede boots and love how easily they pair with dresses (truly!) to give that unexpected tomboy twist to an otherwise feminine dress.

If you like the look of Dr Martens or lace up boots but want a sleeker design with laces, try a lug sole boot. Same vibe, different style.

Shop the Vince Henderson Boot here.

13 / Athletic Trainers

I left this option off last year’s list but this year the sneaker is making a big appearance. Like x4. 2020 is definitely the year of the sneaker and you can’t go wrong with any of them. Let’s break them down!

If you workout a lot, or  you live in leggings, this is the sneaker for you.  You can wear this mainly with your leggings and activewear, which is what I wear half of the week it seems come winter. A nice black trainer that can go from workout to errands; a true team player. I suggest black because this is the easiest color to pair with workout items, no matter the color. Black is my favorite go to for atheleisure so hands down a nice sleek pair of sneakers has to be black. I love a logo, but you can always go with a cleaner look as well!

Shop the Nike Sneaker here.

14 / Worn-In White Sneakers

This look is really in for fall — the worn in sneaker. AKA the Golden Goose sneaker. I’ve fought my love for them for years, even talked some mess about them to cover my tracks. But it’s true — I love Golden Goose sneakers. I love the worn in look, even though they are brand new. This look is adorable with everyday classics — denim, tees, sweaters. But also I love this look with dresses, as well. Mixing the feminine dress with the tomboy sneakers is adorable this fall. (And spring!) These sneakers go well into spring / summer next year too.

Golden Goose will break the bank, so other options are the P448 sneakers and the Veja Esplars. These don’t look as worn in but the same street style vibe is there. You can also just wear a beat up white sneaker — problem solved. 😉


Shop the Golden Goose superstar sneaker here.


15 / Ankle High Top Sneakers

I have been seeing Converse high tops EVERYWHERE lately and I love it. It was the trend I did NOT see coming. It’s so simple and easy — plus what is better than throwing on a comfy pair of sneakers and looking so stylish and cool? This shoe works best with denim, skinny jeans or straight leg that hits right at your ankle would be best. You don’t want the break of the shoe to be covered by your jeans, you want just a little bit of skin showing between the two. With denim, you can pair anything with this shoe — think sweaters, hoodies, simple tees, a crisp button down, etc. If you are wanting an easy everyday sneaker, this is a great option!

Shop the Converse All Star Trainer here.

16 / Chunky Trainers

Last but not least, this is one of my favorite trends to wear: the chunky sneaker. Or dad shoes. You remember the ones, right? Think 1997 dad on vacation at Disneyland, that’s the vibe. I love this look with straight leg denim the most, it really adds to the vintage vibe the dad sneaker goes with. My favorite one from last year is the Reebok Harmon Classic, so if you like the chunky sneaker look but you’re not sure where to start, that is a great option! I’ve actually included a few more options above just because this is a look that’s different for everyone.

Shop the Sneaker here!


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

Shop the Outfit

Fit Details

Monthly Capsule Wardrobe

Each month I create monthly capsules out of my favorite pieces, perfectly curated for each month.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Favorites from the Week

this week’s most loved posts