The Best Fall Shoes to Wear With Every Outfit In 2025

Last Updated on October 19, 2025 by Wendy Sy

As the autumn foliage sets in and the air chills, it’s time for a wardrobe reset to match the mood. One of the first things I do every season is update my fall shoes to literally step into the season feeling refreshed!

Fall is the perfect transitional time to try out different shoe trends, from open to closed-toe styles, and to have fun pairing them with socks and tights.

To me, it’s always worth investing in quality fall shoes since I live in them all season (and often into early winter!). I choose styles that are versatile enough to be worn from morning to night and can easily match with a variety of outfits. 

Up next, you’ll find the best fall shoe categories for 2025, including boots, Mary Janes, loafers, mules, and sneakers.

Best Fall Shoes To Shop In 2025

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1. Boots

The ultimate fall essential, boots are versatile and practical.

In this category itself, there are a ton of different styles of fall boots. Popular ones this season include ankle boots, knee-high boots, cowboy boots, combat boots, and kitten heel booties.

What these boots have in common is seasonal practicality. They’re designed for cooler weather, so they keep you warm and protected. Boots easily complete casual to dressy outfits and have a timeless look. 

One of my all-time favorite boots is these INEZ Valentina Booties that have a neutral espresso color and are handmade in Spain with a plush insole that makes them super comfy. 

I also love the INEZ Paz 70 Mid-Heel Booties in ginger suede. For a more in-depth review on this style, check it out here, and use my code WENDY15 to save 15% off all styles from INEZ.

Shop more boots here:

2. Mary Jane Shoes

Old meets new with this fall shoe trend that’s a fresh take on the ultimate classic: Mary Jane shoes.

This shoe style gives off a charming vintage look with a low-cut front and one or more straps across the instep, complete with a buckle or velcro. 

Traditionally, Mary Janes have a low heel and are made of black leather. For fall 2025, there are many modern versions in a variety of colors, materials, and heel heights.

I always think of fall as a fresh start, whether it’s a new school year or a new work quarter. It’s a time to look back, plan ahead, and even reconnect with your inner child. Mary Janes fit this feeling because they were inspired by a character in Buster Brown, an early 20th-century comic strip by newspaper cartoonist Richard Felton Outcault. Mary Jane (Buster Brown’s sister) wore this shoe style, which became super popular for both kids and adults.

Recently, I got this pair of LifeStride True Mary Jane Pumps in dark cherry patent leather and am so glad I got them early in the season because the style is selling out quickly!

The deep red color and shiny material make it feel elevated, dressy, and modern. I wore these out all day to The Frick Collection museum and Central Park in New York City can say these are truly comfy, thanks to the supportive cushion sole.

Shop more Mary Janes shoes here:

3. Loafers

One of the easiest slip-on-and-go fall shoes that I love is loafers.

Made without laces, zippers, or fastenings, you can just slide into a pair before hitting the door. 

Loafers instantly make any outfit look more polished and are the perfect transition shoe from summer to fall. 

A couple of years ago, I got these Frankie4 Octavia Loafers that I wore all through a trip to New Orleans. The black color and timeless silhouette made them so easy to style in different ways with just a few fall wardrobe options I had in my suitcase.

I also love these Tuckernuck White Pebbled Rowan Leather Loafers (now on final sale) that I got over the summer and have been wearing a lot lately with my fall outfits.

The closed-toe style makes it work well for mild fall weather and can be paired with tights for extra warmth. 

Wear them with everything from dress pants to jeans to a skirt — it’s an easy way to look put together in a cinch.

Shop more loafers here:

4. Mules

Fall fashion isn’t complete without a good pair of mules. 

Similar to loafers, you can just slip them on and go, but it’s even easier. 

What makes mules special is their backless style. For the new season, there are the cutest new mules that are just right for that in-between fall weather.

There’s also a variety of toe shapes that mules come in that totally change the look and feel of them. For someone who’s 5’1″, I love pointy-toe styles since they have an elongating effect.

As for the heel heights, mules come in flats, low heels, to high heels. My favorites are low block heels that make them more comfortable to walk around in.

What I love most is that mules go with everything that a boot would and gives a sleek, effortless look.

Throw them on with a pair of tights and a mini skirt and sweater, and you’re ready to go!

Shop more mules here:

5. Sneakers

And of course, the quintessential comfort shoe: sneakers.

These athletic-inspired shoes are made with flexible rubber soles and are supportive for all-day walking. 

Fall often means being on your feet — exploring places and enjoying the outdoors before it gets too cold. Comfy sneakers let you focus on your plans and not pain from your shoes.

Although I have a lot of sneakers, the ones I reach for again and again are white sneakers like this Frankie4 pair that are designed by a podiatrist. These go with most of my casual outfits and give that effortlessly cool street style. 

I love pairing sneakers with a slip dress and cardigan or straight leg jeans and a cashmere sweater. Other styles I love are leather sneakers and ones with chunky soles for a bold statement. 

Shop more sneakers here:

Whether you’re layering up for a crisp morning walk, going to work at the office, or meeting up with friends for a cozy pumpkin spice latte, the right pair of fall shoes can completely transform your look. 

From the timeless charm of Mary Janes to the sporty look of sneakers, each of these fall shoes styles brings something special to your wardrobe.

Ready to refresh your fall shoes collection? 

Shop the picks now and find the perfect styles to match the autumn aesthetic!

Shop The Story: Best Fall Shoes

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