Photo illustration: the strategist; Photo: retailer

October Prime Day is here. Follow them all to find the best deals in each category 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 of deals – some bad, some good and some terribly 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 know what’s worth watching 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 of most sizes, and the markdowns are comparable to Levi’s own sales. Calvin Klein underwear and Crocs sandals are always a good choice – already pretty cheap at full price, they’re even cheaper right now. Some of the biggest discounts can be found in the sale sections of Shopbop and Zappos, where you can find Dr. Martens boots and Madewell tank tops. Last Prime Day I spent much of my workday among them, and I’ll do the same this time. Below you’ll find the best fashion deals from the sale, including some Gap pull-on pants and Havaianas that are a real bargain. 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 top a few of our “Best in Class” lists…

… Just like the Ribcage, which we have been calling the ‘Goldilocks of jeans’ since 2019 (because of that ‘extremely high’ waist).

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

Some comfortable ‘chinos’ – with a terribly elastic waistband and drawstrings.

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’s striped!)

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

…And an unlined, underwired bralette that you’ll forget you’re wearing.

This is the platform, fake-fur-lined version of Docs’ 2976 Chelsea boots (which are so durable that my father used to wear a pair while packaging pharmaceuticals on a factory floor).

There was a moment when you couldn’t get in New York office without seeing (at least) one employee in Vejas. They’re still cool years later.

You won’t be nursing blisters on the back of the heel as you break it in.

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

Or go for the Havaianas with thinner straps so that you feel (almost) barefoot.

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

The 550s are cut wider through the thighs than the 501s (especially important for those who don’t skip leg day).

A not too crazy ‘Cowboy Cut’.

Less striking than a Ralph Lauren teddy bear sweater, but just as preppy!

For one Industry off-duty look if you’re in the country (or upstate).

You can put your old, worn-out Weejuns to rest.

Their first Merrells – matching your own Moabs.

For the baby who starts running fast enough.

I don’t think you’ll find anything cuter than this as you scroll through the sale!

These are the children of the aforementioned chinos.

Save for future family parties.

The Strategist is designed to provide helpful, expert recommendations on things to buy across the vast e-commerce landscape. Each product is independently selected by our team of editors, which you can read about here. We update links where possible, but note that offers may expire and all prices are subject to change.