The 34 best fashion deals for Prime Day in October 2024

Photo Illustration: The Strategist; Photo: Retailer

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

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

Above all, it is one of the best times to buy Levi's jeans. Amazon's inventory is full in most sizes and the discounts compete with Levi's own sales. Calvin Klein underwear and Crocs sandals are always a good choice – they're pretty cheap at full price, but they're even cheaper right now. Some of the biggest discounts are in the sale sections of Shopbop and Zappos, where you can find Dr. Martens boots and Madewell tanks can be seen. This past Prime Day, I spent much of my work day window shopping among them, and this time I'll be doing the same again. Below are the best fashion picks from the sale, including a pair of Gap pull-on pants and Havaianas that are a steal. You should also take a look at our main Prime Day hub for our Deal Editor's definitive list of the best deals across all categories, from toys to home essentials.

The Wedgies are the jeans you've seen all over the Strategist archives and are at the top of some of our Best in Class lists…

… Just like the rib cages, which we have been calling the “Goldilocks of jeans” since 2019 (because of their “insanely high” waist).

If you're still not sold on the barrel leg, the Baggy might be a better choice.

Some comfortable “chinos” – with a very stretchy waistband and drawstring.

I know the word “simple” gets thrown around a lot when talking about t-shirt dresses, but this really is the simplest t-shirt dress. (Plus it's striped!)

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

…And an unlined, wire-free bralette you'll forget about.

This is the platform incorrect-Fur-lined version of Docs' 2976 Chelsea boots (which are so durable my dad wore a pair while packing medicine at a factory).

There was a time when you couldn't go in new York Office without seeing (at least) one employee in Vejas. They're still cool years later.

You will not have blisters on the back of your heel when breaking in.

It may no longer be the season of “adventure sandals,” but that will come sooner than you think.

Or opt for the Havaianas with narrower straps to feel (almost) barefoot.

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

The 550s are cut wider in the thighs than the 501s (especially important for those who don't miss a leg day).

A not too intrusive “cowboy cut”.

It's less flashy than a Ralph Lauren teddy bear sweater, but just as neat!

For one industry Casual look for when you're out in the country (or in the hinterland).

You can give your old, beat-up Weejuns some rest.

Your first Merrells – to match your own Moabs.

For the baby who will soon walk.

I don't think you'll find anything cuter when you scroll through the offerings!

These are the children of the chinos presented previously.

Save for future family holidays.

The strategist is designed to deliver useful, expert buying recommendations across the e-commerce landscape. Each product is independently selected by our editorial team for you to read about Here. We update the links when possible. However, please note that offers may expire and all prices are subject to change.