Originally published October 12, 2021. Updated October 2, 2026 with current shopping picks and more outfit ideas.
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One of the reasons why I love fall so much is because of the shoe options. THEY ARE ENDLESS. Boots with denim, sneakers with a dress, a little heel with a knit: changing the shoe is such an easy way to change the whole outfit.
The five types worth thinking about are boots and booties, mules, clogs, sneakers and heels. You do not need a new pair in every category. Start with the gap in your actual week: walking, work, relaxed weekends or evenings out.
Which fall shoes make sense for your wardrobe?
- Boots and booties: the covered-up option for jeans, trousers and longer skirts. Choose the shaft height around the hems you wear most.
- Mules: easy for mild, dry days. A closed-back loafer gives a similar polished look when you want more coverage.
- Clogs: relaxed with straight-leg denim and visible socks. An open heel is a fall styling choice, not protection for snowy sidewalks.
- Sneakers: the casual anchor for denim, knits and dresses. Check fit and support for your own walking plans.
- Heels: an outfit finisher for dinner or an event. A low heel and a hem that clears the ground make the styling easier.
Current shoe picks to shop
These options come from my ShopMy selection. Prices and sizes can change; check your size before ordering. My original personal shoe notes are below.
A black boot for dressier denim
Madewell Dimes kitten-heel boots in True Black ($218 when checked) have a two-inch heel and rounded toe. The crinkled leather adds texture without another color to coordinate. Try them beneath wide-leg jeans or trousers with a simple knit. Let the hem skim the boot rather than bunch around the ankle.
For a denim option, Madewell’s Short Perfect Vintage wide-leg jeans in Bedford Wash have a cropped, shorter-length cut. Compare the listed inseam with your own jeans; a “short” cut will not land at the same point on everyone. Shopbop advises sizing up in the Dimes boots, so read its current fit notes before choosing.
A suede loafer for a softer everyday look
Free People Carry On suede loafers in Tobacco Oiled Suede ($168 when checked) are a closed-back alternative to a mule. The warm brown works with cream, navy, faded denim and black. Wear them with an ankle-length trouser for a little space above the shoe, or let a wider jean fall over the upper.
A brown knit keeps the outfit tonal: the Alex Mill Lennox cotton sweater in Dark Chocolate is one option, although only size L was available at the time of this update. A knit you already own works just as well. Keep suede pairs for dry weather unless the manufacturer specifically says otherwise.
A brown sneaker to wear with denim or a skirt
ALOHAS Tb.56 suede sneakers in Brown ($245 when checked) offer a low-top shape, suede upper and rubber sole. Pair them with the Bedford-wash wide-leg jeans and a white tee, or use the brown as the grounding color below a cream skirt. These are a casual styling option; I am not presenting them as a tested all-day walking or winter-weather shoe.
For outfits that need a little more structure, add a blazer. There are more combinations in how to style a tweed blazer with jeans, trousers and a simple knit.
Fall shoes versus winter shoes
A shoe that looks great with a winter coat is not automatically a snow boot. For rain, slush or ice, check the maker’s waterproofing and outsole details and choose footwear suited to the conditions. Save open-back mules, suede sneakers and dress heels for dry days or indoor plans. When walking is the priority, start with my guide to shoes for walking around NYC.
My original fall shoe notes
The personal experiences below are from the original October 2021 article. The current shopping picks above are newer options, not products I am claiming to have personally tested.
Boots & Booties
Boots and booties are obviously a MUST HAVE for fall and winter. There’s nothing worse than cold feet when you’re walking around. Shopping for boots are actually so overwhelming for me. There’s always a new style or trend. But I think there are a couple of boots and booties that are non-negotiable and will forever be a classic, like knee high boots. I wanted to include some trendy boots too, as a few of them have actually been in my closet for 2 seasons now.
- Lug Sole Boots: As a petite person, I think that lug sole boots are actually quite flattering. I love how the fitted shaft helps to elongate your legs. I also love the juxtaposition between that and the thick sole.
- Winter Boots: I typically reach for my waterproof boots (YES, THEY’RE SUEDE!) when I’m looking for an outfit completer. I also just bought these UGG boots for COLD COLD COLD days where my feet pretty much need to feel like they’re in a blanket (also waterproof).
- Knee High Boots: These are the boots that are CLASSIC and will be in your closet forever. I remember when I was SO into over the knee boots, but have found that knee high boots just look and feel better on me.
- Combat Boots: I bought my Chanel combat boots in 2019 and they might be my most worn. I love them SO much. I recently saw these Prada boots, but could not justify the price. A few weeks ago, I had some time to kill before getting my new tattoos, so I went into Urban Outfitters. I found these boots and walked out of the store with them.
- Heeled Booties: And finally a pair of boots for when you wanna be dressier.
Mules
I love wearing mules during fall. I particularly love my Gucci mules with the fur. I wrote this post about styling Gucci shoes, and how they’re my most worn shoes. I think they’re great for every type of outfit. And 10000% worth the investment. I was talking to someone who has had their Gucci shoes for almost 8 years. That alone should be a reason to buy them! The (faux) fur ones are perfect for fall. I love that they give the ultimate cool girl vibes.
Birks
I’ve been on the Birkenstock bandwagon for years now. I love how they give off the “I don’t really care” vibes, but still make your outfit dope. Last year, I bought the shearling option, and this year I decided to buy the clog version. I love them all equally. Even though they’re certainly not the most attractive looking shoe, I think they’re SUCH a cool girl option.
Sneakers
I was never a sneaker girl. And then I got a pair of Air Max 90s are LOOOOOVED them. I realized I could wear them with more outfits than I thought. So I started purchasing more. I think they’re the perfect swap for your sandals. I really love the Nike Blazers. I got them in March, and pretty much wear them every weekend. When it comes to wearing sneakers with more casual looks (or even dresses), I typically reach for my white Nike Air Max or Everlane sneakers. They add a little bit of a masculine tough to feminine outfits, and I really love that!
Heels
There’s something about pairing a fall/winter outfit with a pair of heels. I LOVED this option from Ann Taylor. I think they’re so easy and so classic. After not putting on a pair of heels for all of 2020, I’ve definitely been gravitating more towards heels when we have a date night or an event.
Shop the original post
The original LTK edit is below; some older styles may no longer be available. Use the current picks above for the updated selection.
