The 5 Shoes You Need for Fall
Shoes can truly make or break an outfit, and having the right lineup in your closet makes getting dressed so much easier. When the seasons change, I always reassess my footwear, because what works in July (or even a few Octobers ago) isn’t necessarily what works in October. And so many of us fall into the cycle of having sandals and boots, but nothing in between for this seasonal shoe purgatory.
This fall, these five shoes are the ones I consider absolute wardrobe essentials.
1. Daytime Ankle Boot
This is your everyday workhorse. Lower, walkable heel. Comfortable. Goes with jeans (both long and cropped, both slim and wide), dresses, or even trousers. The key is a tighter, higher shaft AND an elongated, pointy or almond shaped toe. It’s literally the polar opposite of the ankle booties from 10 years ago.
If you only invest in one ankle boot for fall, make it this one. It’ll carry you through everything from errands to casual nights out.
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2. Nighttime Ankle Boot
Think taller heel, pointier toe, and an overall dressier look. This is the ankle boot you wear out to dinner, to a girls’ night, or to dress up your favorite denim. It’s a pump but in a bootie. Heel height is up to you. I’ve given you a variety of options.
It gives your outfits that little extra oomph when you want to feel polished.
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3. Ballet Flat or Loafer
A sleek, close-to-the-ground shoe instantly makes any outfit look more polished. Whether you go for a classic ballet flat or a menswear-inspired loafer, this is the perfect option when you want something that feels chic but still comfortable. Opt for a more streamlined sole, less lug sole, to give it a sleek, more sophisticated feel.
Great for transitional weather when sandals feel too summery but boots feel too wintery.
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4. Sleek Sneaker
Yes, sneakers belong on this list! If you read my Fall 2025 Trend Report, you know that sleek sneakers are having a moment this fall. Think of these as a fashion sneaker, not an athletic sneaker. They can be comfortable, and you can walk miles in them, however, these are not your Orange Theory sneaks.
A clean, minimal sneaker works for everything from travel days to running around town. Look for one that feels elevated (think leather, suede, or a sleek silhouette) so it pairs easily with jeans, joggers, trousers, or even dresses.
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5. Tall Boot
The tall boot has made a full comeback, and I couldn’t be happier. With a slight heel and a shaft that hits at or just below the knee, they instantly elevate skirts, dresses, and even slim trousers. You can go for a tight-fitting pair that hugs your leg (great for dresses/skirts) or a looser style that feels more relaxed (perfect for tucking jeans/pants into). Take note, these are not your riding boot of years past. The modern tall boot has less hardware and a sleeker toe box (not as round) so it feels more streamlined and less chunky/clunky.
If your older boots are not quite cutting it, the shape might be why. See if an updated silhouette helps your outfits feel more current.
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Bonus: If You’re an Overachiever Like Me
Technically, I said 5 shoes. But if I’m being honest, I could easily stretch this list to 6 or 7. I’d break the tall boot into two categories:
Tight-fitting tall boots (wear with skirts, dresses, and wide, cropped pants).
Loose-fitting tall boots (great with jeans tucked in or with more relaxed outfits).
And I can’t resist adding a suede pump. It’s one of those versatile dressy shoes that looks perfect in the cooler months when patent or satin feels too summery.
Bottom line: These five (or eight, if you’re going for extra credit) styles will cover just about everything fall throws at you, from casual mornings to polished evenings!