Shopping·5 min read

Just Wear This: Shoes, Shoes, Shoes

just wear this october 2025
Design: theSkimm | Images: Steve Madden, Madewell
September 30, 2025

Products you buy through our links may earn us a commission. Oh, and if something's out of stock, oops, it was there (and all prices were accurate) at time of publication.

Nothing makes an outfit quite like a great pair of shoes. These are the trendiest — yet most wearable — styles we could find. Consider them auto-approved by your coolest friend.

The Tall Boots

steve madden boots
Design: theSkimm | Images: Steve Madden, Aritzia, Uniqlo, Coach Outlet, Oak and Luna

Riggs Black Leather Boots ($199.95, Steve Madden)

Wear them with:


The Ankle Boots

sam edelman ankle boots
Design: theSkimm | Images: Sam Edelman, Madewell, Gap, Reiss, Charles & Keith, Mejuri

Paige Ankle Boot ($160, Sam Edelman)

Wear them with:

The Loafers

franco sarto loafers
Design: theSkimm | Images: Nordstrom Rack, Favorite Daughter, J.Crew, Naadam, Michael Kors, Quince, Nordstrom

Franco Sarto Alora Penny Loafer ($59.97, Nordstrom Rack)

Wear them with:

The Sneakers

dolce vita sneakers
Design: theSkimm | Images: Dolce Vita, Abercrombie & Fitch, J.Crew, Vagabond, Missoma

Serina Sneakers ($140, Dolce Vita)

Wear them with:

The Ballet Flats

madewell flats
Design: theSkimm | Images: Madewell, Tuckernuck, Banana Republic, Levi's, Reformation, Quay, Mon Été

The Greta Ballet Flat ($79.99+, Madewell)

Wear them with:

The Clogs

seychelles clogs
Design: theSkimm | Images: Nordstrom, Everlane, H&M, Free People, Gap

Seychelles New Routine Mule ($109, Nordstrom)

Wear them with:

Live Smarter

Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.

© 2012-2026 Everyday Health, Inc., a Ziff Davis company. All rights reserved. theSkimm is among the federally registered trademarks of Everyday Health, Inc., and may not be used by third parties without explicit permission

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.