The Best October Prime Day Fashion Deals

October Prime Day is here. To find the best deals in every category, follow all of our Prime Day coverage. 

Today’s the official beginning of this year’s October Prime Day (the third in a row now). It’s just like July Prime Day with two days’ worth of deals — some bad, some good, and some very good. It’s become an annual tradition for me to find the best fashion deals for the site. As the Strategist’s style writer, I can tell what’s worth checking out and what’s worth ignoring for your wallet’s sake. A good rule of thumb: If a deal’s less than 20 percent, don’t bother.

It’s one of the best times to buy Levi’s jeans, especially. Amazon’s inventory is full of most sizes, and the markdowns rival Levi’s own sales. Calvin Klein underwear and Crocs sandals are always sure bets — already pretty cheap at full price, they’re even cheaper at the moment. Some of the deepest discounts come courtesy of the Shopbop and Zappos sale sections, where you’ll see Dr. Martens boots and Madewell tanks. This past Prime Day, I spent much of my workday window-shopping between them, and I’ll be doing the same this time around again. Below, you’ll find all the best fashion deals from the sale, including a pair of Gap pull-on pants and Havaianas that are a real steal. You should also check out our main Prime Day hub for our deal editor’s definitive list of the best deals across all categories, from toys to household essentials.

The Wedgies are the jeans you’ve seen all over the Strategist archives and at the top of a few of our “Best in Class” lists …

… As are the Ribcages, which we’ve been calling the “Goldilocks of jeans” (for that “deliriously high” waist) since 2019.

If you’re not yet sold on the barrel leg, the Baggy might be a better bet.

Some comfortable “chinos” — featuring a very stretchy waistband and drawstring ties.

I know the word “easy” gets thrown around a lot when it comes to T-shirt dresses, but this really is the easiest T-shirt dress. (Plus, it comes striped!)

Make a matching “My Calvins” set with these not-too-cheeky boyshorts …

… And an unlined, wire-free bralette that you’ll forget you have on.

This is the platformed, faux-fur-lined version of Docs’ 2976 Chelsea boot (which are so hard-wearing my dad used to wear a pair while packaging pharmaceuticals on a factory floor).

There was a point in time when you couldn’t go into the New York office without seeing (at least) one staffer in Vejas. They’re still cool years later.

You won’t be nursing back-of-the-heel blisters while breaking these in.

It’s not “adventure sandal” season anymore, but it will be sooner than you think.

Or go for the Havaianas with slimmer straps to feel (almost) barefoot.

A slim-fit version of the original true-blue jean from 1873.

The 550s are cut roomier in the thighs than the 501s (especially important for those who don’t skip on a leg day).

A not-too-yee-haw “Cowboy Cut.”

It’s less obvious than a Ralph Lauren teddy-bear sweater, but equally preppy!

For an Industry off-duty look when you’re countryside (or upstate).

You can put your old beat-up Weejuns to rest.

Their first Merrells — to match your own Moabs.

For the baby who’ll be be running soon enough.

I don’t think you’ll find something cuter than this while scrolling through the sale!

These are the children of the chinos featured earlier.

Save for future family holiday parties.

The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.