
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.

Black Leather Ryder Boots ($475, Tuckernuck)
Wear them with:
Gardenia Dress ($228, Aritzia)
Corduroy Short Jacket ($69.90, Uniqlo)
Asher Shoulder Bag With Cow Print ($279, Coach Outlet)
Twisted Rectangle Hoop Earrings ($75, Oak and Luna)

Axelle Ankle Boots ($255, Sézane)
Wear them with:
High-Rise Bootcut Trouser ($168, Madewell)
Rib Mockneck Tank Top ($24, Gap)
Lia Wool-Blend Double-Breasted Blazer ($290, Reiss)
Simone Shoulder Bag ($103, Charles & Keith)
Boa Gemstone Coil Ring ($168, Mejuri)

New Winona Penny Loafers ($198, J.Crew)
Wear them with:
The Favorite Pant ($218, Favorite Daughter)
Classic Belt in Italian Leather ($59.50, J.Crew)
The Classic Tee ($38, Naadam)
Essex Silver-Tone Watch ($200, Michael Kors)
14K Gold Lab Grown Diamond Martini Studs ($200, Quince)
Sam Edelman Small Poppy Drawstring Leather Crossbody Bag ($195, Nordstrom)

Serina Sneakers ($140, Dolce Vita)
Wear them with:
Mid Rise 90s Straight Jean ($76.50, Abercrombie & Fitch)
2025 Rollneck™ sweater in rugby stripe ($98+, J.Crew)
Cannes Bag ($375, Vagabond)
Cropped Twill Workwear Jacket ($110, Abercrombie & Fitch)
Chubby Tunnel Huggies ($118, Missoma)

The Greta Ballet Flat ($79.99+, Madewell)
Wear them with:
Brushed Wool Leopard Drew Short Trench Coat ($198, Tuckernuck)
The Everyday Shirt ($90, Banana Republic)
501® ‘90s Ankle Jeans ($68.60+, Levi’s)
Small Vittoria Tote ($398, Reformation)
Vibe Check ($95, Quay)
The Elise Earrings ($75, Mon Été)

Seychelles New Routine Mule ($109, Nordstrom)
Wear them with:
Loose Curve Jean ($148, Everlane)
Twill Car Coat ($54.99, H&M)
Essential Triangle Bandana ($28, Free People)
CashSoft Crewneck Sweater ($47, Gap)
Oversized Leslie Tote ($198, Free People)
Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.
© 2012-2025 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.