Shopping·5 min read

Just Wear This: Shoes, Shoes, Shoes

just wear this october 2025
Design: theSkimm | Images: J.Crew, Tuckernuck, Sézane
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

tuckernuck boots
Design: theSkimm | Images: Tuckernuck, Aritzia, Uniqlo, Coach Outlet, Oak and Luna

Black Leather Ryder Boots ($475, Tuckernuck)

Wear them with:

The Ankle Boots

sezane ankle boots
Design: theSkimm | Images: Sézane, Madewell, Gap, Reiss, Charles & Keith, Mejuri

Axelle Ankle Boots ($255, Sézane)

Wear them with:

The Loafers

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

New Winona Penny Loafers ($198, J.Crew)

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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