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:

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