69 Best October Prime Day Fashion Deals: Madewell to Vince

69 Best October Prime Day Fashion Deals: Madewell to Vince

Photo-Illustration: The Strategist; Photo: Retailer

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

Today’s the last day of this year’s October Prime Day. Just like the two-day July Prime Day, there are still lots of deals to be had on the megaretailer’s site — some bad, some good, and some very good. And after covering Prime Day for years as the Strategist’s style writer, I can tell you what’s actually worth checking out and what’s worth ignoring for your wallet’s sake. A good rule of thumb: If the deal’s less than 20 percent off, don’t bother — even if you’re feeling that last-minute rush.

Yesterday, I spotted lots of Levi’s jeans and Gap shirts marked down. You’ll still see these on sale today — plus, single-digit Hanes tees and Croc slides for half off. Some of the day’s best discounts also come courtesy of the Shopbop and Zappos sale sections, where there are markdowns on Free People jackets and Hunter boots. Here, you’ll find all of the best Prime Day fashion deals that are live (for now). Because the deals expire tonight — at 2:59 a.m. EST sharp — you don’t want to dillydally. Stock tends to move quickly in the evening hours especially.

Be sure to check out our main Prime Day hub for our deal editor’s definitive list of what to get across all categories, from toys to household essentials, and the best Prime Day deals, according to Strategist writers. And you should sign up for our sales newsletter to be up to date on all the actually good deals across the internet (for Prime Day and beyond).

Every Prime Day, you can expect to see discounted Levi’s. But if you’re only going to buy one pair, you should get the Wedgies, our longtime favorite jeans. They’re as cheap as they were on Prime Day proper last July. There are a few Madewell T-shirts marked down, but your best bet is the whisper-thin turtleneck. It’ll be a great base layer, especially under a big puffer and long scarf. And another worthwhile find is this pair of Sam Edelman flats that are almost half off. They’re a good dupe for those Alaïa flats you’ve seen on many a celebrity, for one-tenth of the price of the real thing.

Gap Poplin Big Shirt

Gap Relaxed Pocket T-shirt Dress

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.

Kule the Tank Dress

A super-versatile tank dress from the king of stripes, Kule.

Norma Kamali Kamali Kulture Rectangle Jog Jumpsuit

Norma Kamala cuts a mean jumpsuit, and this one’s no exception!

Solid & Striped The Annemarie One-Piece

Go on, book that vacation — you’ll have your swimsuit of choice sorted.

Free People All Star Shorts

You can sport these not-too-short shorts after your running club’s run.

Eberjey Gisele Short Sleeve and Cropped Pant PJ Set

Lunya Washable Silk Tee Set - Caffeinated Pink

You won’t regret making the switch to sleeping in silk — and this is machine-washable pair is our pick for the best silk pajama set.

Free People Hot Shot Jumpsuit

A onesie you can actually be seen in outside the house.

Hanky Panky Signature Lace Low-Rise Thong (3-Pack)

When it comes to thongs, Hanky Panky reigns supreme.

Calvin Klein Modern Cotton Boyshort Panty

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

Calvin Klein Modern Cotton Bralette

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

Sam Edelman Michaela Mary Jane Flat

This Alaïa dupe is now ten times cheaper than the real thing.

Dr. Martens 1461 Flower

And these might be the prettiest Docs I’ve ever seen.

Crocs Mellow Clog

A pair of Crocs that doesn’t look like a pair of Crocs…

Crocs Stomp Slide

… And a pair of Crocs that do look like a pair of Crocs.

Hunter Classic Rain Boot

So you don’t have to keep jumping across muddy puddles.

Veja V-90 Sneakers

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.

Superga 2402 Cotw Sneaker

You won’t need socks for these backless Supergas.

Loeffler Randall Landon Ballet Flat

You can take these go-with-everything ballet flats everywhere.

Franco Sarto Tinsley Mary-Jane Flat

Madewell Dimes Kitten-Heel Boots

A heeled boot for those who don’t trust themselves with heeled boots.

Schutz Maryana Block Boots

A knee-high boot that doesn’t lean too equestrian.

Cole Haan Piper Mule

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

Chacos ZX/2 Classic Sandal - Line Hang Teal

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

Sorel Joanie Heel Slide Sandals

They seem orthopedic (complimentary).

Loeffler Randall Sawyer Sandals

L’eggs Leggswear Seasonless Tight

Falke Bedsock Socks

I’m picturing these peeking out under a cropped hem.

Madewell the Sling Cross-body Bag

Keep your essentials within easy reach.

Madewell The Zip-Top Essential Tote

A walking junk drawer for everything you need for the office.

Bembien Amalie Bag

To live out your Jane Birkin–carrying–around–a–basket fantasy.

Le Specs Outta Love Tort Sunglasses

Add a tortoiseshell headband from C.O. Bigelow and you’re basically Carolyn Bessette-Kennedy.

Madewell the Essential Leather Belt

Here’s the simple belt you’ve been trying to hunt down.

Jenny Bird Small Icon Hoops

For those who are strictly into silver.

Jennifer Behr Edith Earrings

Formal enough earrings for every wedding you’ll ever have to attend.

Levi’s 501 Slim-Fit Jeans

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

Levi’s 550 Relaxed-Fit Jeans

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

Wrangler Cowboy Cut Original-Fit Jeans

A not-too-yeehaw Cowboy Cut.

Vince Griffith Chino Pants

Office-appropriate pants for those gunning for a raise.

Vince Birdseye Johnny Collar Polo

And a video-call-ready polo for those big meetings with your bosses.

Madewell Brushed-Terry Hoodie Sweatshirt

A replacement for your holey Champion.

Lacoste Long-Sleeved Regular-Fit V-neck Organic-Cotton Sweater

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

A.P.C. Washed Stretch New Denim Jacket

It’s a small investment, but this A.P.C. denim jacket is the only denim jacket you’ll ever really need.

Calvin Klein Cotton Classics Briefs (5-Pack)

Cole Haan Pinch Penny Slip-on Loafer

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

Sperry Avenue Duck Boot

They’re a lot cheaper than L.L.Bean’s Bean Boots, and they’ll do the walking-through-slush job just as credibly.

Polo Ralph Lauren Signature Knit Scarf

A warm wool scarf for the months ahead.

Saucony Baby Jazz Hook Loop Sneaker

For the baby who will be running soon enough.

Dr. Martens Maccy Mary Jane (Little Kid/Big Kid)

For the budding “brat.”

The Children’s Place Girls’ Solid Cardigan

Gap Baby Soft Knit Garter Hat

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

Gap Baby Boys’ Rib-Waist Pull-on Khaki Chino Pant

These are the children of the chinos featured earlier.

Simple Joys by Carter’s Two-Pack Stretch Rib Dresses

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.

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