JAKE WOOLF

Share this post

User's avatar
JAKE WOOLF
25 Pairs Of On-Sale Shoes That You’ll Actually Want To Wear

25 Pairs Of On-Sale Shoes That You’ll Actually Want To Wear

Discounted shoes that’ll have legit staying power in your wardrobe.

JAKE WOOLF's avatar
JAKE WOOLF
Jul 15, 2025
∙ Paid
8

Share this post

User's avatar
JAKE WOOLF
25 Pairs Of On-Sale Shoes That You’ll Actually Want To Wear
1
Share

Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes.

The insatiable and slightly twisted world of fashion means that summer sale season is already upon us. So despite the fact that it’s only mid-July, deals can be had on all sorts of quality seasonal attire, from polos to pleated plants to sunglasses—all of which you can still get serious mileage out of before Labor Day. But since it’s Shoesday, today I’m focusing in on footwear that’s available for the low.

That said, just because something’s on sale doesn’t mean you should buy it. Often, the fact that something’s marked down is simply because, well, no one wanted it. So I wanna be clear I’m not here to help stores offload subpar products that were basically doomed from the jump by virtue of being too trendy, too expensive, or flat-out too ugly. Instead, I’ve poured through hundreds of e-commerce pages in search of shoes that, while discounted from their original MSRP, are ones you’ll actually want to wear—not just this summer, but for many to come.

Below, I’ve broken down this list of 25 great shoes (17 of which are under $200) into three simple categories that define any pared down summer rotation: loafers, sneakers, and sandals. In each section are shoes that are built for the long haul, and sure, will save you a few bucks. Anyway, let’s get to it. Enjoy!!!

OTHER POSTS YOU MIGHT LIKE:

New York’s Coolest LES Shop Made The Perfect Summer Shoe

My Favorite Clothes of 2025 (So Far)

Every Pair Of Shorts I’m Actually Wearing This Summer

The Best Clothes I Saw In Italy

The Minimalist Shoe Brand That Quietly Took Over My Closet

Everything I Packed For My Trip To Italy

How One Of My Favorite T-Shirts Gets Made

My 50 Favorite Under $100 Style Items For Summer

I Talked To The Man Who Made The Perfect Knit Polo

My Favorite Under $100 Summer Shoes

This newsletter is ENTIRELY funded by subscriptions. I don’t use affiliate links, and all of these products are things I’ve endorsed because I actually like them—though in some cases I did not pay for them. Point is, your subscriptions are both extremely cool and very much appreciated. Thank you!

25 Pairs Of Shoes That Are On Sale But You’ll Actually Want To Wear

Keep reading with a 7-day free trial

Subscribe to JAKE WOOLF to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Omnipotent Inc.
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share