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These Editor-Selected October Prime Day Fashion Deals Are My Secret to a Stylish Autumn Wardrobe

Don't miss your chance to score savings on coveted brands like Levi's, Coach, and Madewell.

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street style lfw september 2025 day two
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I don't know about you, but something about the first few weeks of fall makes me want to revamp my entire wardrobe. Thanks to Amazon's Prime Big Deal Days sale (which runs from today, October 7, through tomorrow, October 8), you don't need to blow an entire paycheck to treat yourself to some new duds. I spotted adorable fashion finds starting at just $9. But you have to act fast—unlike July, Prime Day 2.0 is only 48 hours long.

More October Prime Day deals, right this way..

As a shopping editor who's been covering Prime Day for years, I can usually count on the steepest discounts dropping during this time of year. That includes massive markdowns on fall-ready Levi's denim, tons of cozy sweaters, and a best-selling Madewell tote bag for 25% off. If these Prime Day fashion deals sell out before you have a chance to scoop them up, don't say I didn't warn you.

Before settling in to binge-watch all of Gilmore Girls, best believe I'll be slipping into a cute and cozy lounge set like this shorts-and-crewneck combo. Bonus points for the adjustable drawstring waistband!

Ribcage Straight Full Length Jeans
Now 30% Off

There's a reason why Cosmo editors (and celebs like Hailey Bieber and Zendaya) keep wearing Levi's jeans: the fabric feels super high-quality, and they come in a ton of timeless and trendy styles like this straight-legged pair—which can be yours for under $50.

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3
this celeb-adored sneaker brand

Adidas Grand Court Alpha 00s Sneaker

Grand Court Alpha 00s Sneaker
Now 20% Off

Bella Hadid, Kendall Jenner, and Olivia Rodrigo all wear Adidas sneakers...and now you can too, thanks to this steep discount. These trendy low-profile kicks have a faux suede outer, which feels extra on-theme for fall.

Once it starts to get chilly out, you'll be grateful to have this oversized moto jacket on hand—it even has roomy pockets to keep your hands warm. Just note that it runs quite large, so reviewers recommend sizing down for a less bulky fit.

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These knot-shaped studs are proof you don't have to spend a fortune on cool-looking jewelry. They also come in silver and a two-toned version, if you're so inclined to try out the mixed metal trend.

When in doubt, this midi-length sweater dress is an easy one-and-done piece that you can wear to the office, date night, holiday parties, and beyond. Try styling it over knee-high boots for a sophisticated look.

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I'm loving the preppy vibe of this cable-knit polo sweater, and its short sleeves make it ideal for still-warm fall days. Try tucking it into a pair of trousers or a pleated skirt to lean into its country club aesthetic.

Honestly, my jaw dropped when I saw this Madewell tote on sale —in the season's hottest chocolate suede hue, no less. I recommend snapping her up ASAP before she goes back up to full price...

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I like to call this top my "safety" going-out top, since the asymmetrical neckline is super flattering and it works for pretty much every occasion. So if you see me wearing it every weekend this fall... mind your business.

Whether worn beneath bootcut jeans or styled with a teeny-tiny mini skirt, these knee-high boots will be a workhorse in your fall wardrobe. I love how this pair has a block heel and platform toe, so they feel dressy enough for nights out.

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11
these low-rise jeans

Levi's Superlow Jeans

Superlow Jeans
Now 30% Off

Snag these effortlessly cool and casual low-rise jeans while on sale for 40 percent off! These relaxed and loose jeans are a call back to the early aughts, so naturally, we're obsessed.

12
this voluminous dress

Petal & Pup Belle Maxi Dress

Belle Maxi Dress
Now 20% Off

Perfect for an upcoming wedding, this gorgeous tulle dress is just under $100 on sale. Featuring a square neckline, ruffle detailing and a drop-tiered ruffle skirt, you'll feel like a princess in this number. You can also snag it on a steeper discount in other colors.

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13
this cozy cat sweater

Cider Cat Sweater

Cat Sweater

Spooky season is upon us, so to get into the spirited mood, we're adding this eerie cat sweater to our fall wardrobe. It's cute, fun, and best of all, oh so comfortable and soft. For $20, it'll pay for itself over time!

Madewell makes some of the highest-quality belts in my rotation, and this otherwise simple black pick has sculptural gold accents that really make it stand out, in my opinion. But if you're not a gold girlie, it's also on sale in silver.

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15
these budget-friendly leggings

Colorfulkoala High Waisted Yoga Pants

High Waisted Yoga Pants
Now 21% Off

Leggings can get seriously expensive, which is why thousands of Amazon reviewers swear by this affordable pair from Colorfulkoala. They're made from a soft, brushed fabric that shoppers say is comparable to pricer brands. And did I mention they have pockets?

16
these trendy suede sneaks

New Balance 515H V1 Sneaker

515H V1 Sneaker
Now 26% Off

Soft suede fabric? Check. Olive green color? Check. Cushy platform sole? Check. If I'm not mistaken, these New Balance sneakers tick all the boxes for a perfect fall shoe. And with an impressive 4.7/5 star rating, you really can't go wrong.

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17
this elevated travel outfit

AUTOMET Sweatsuit

Sweatsuit
Now 39% Off

Ahead of your holiday vacay plans, be sure to snag this snuggly two-piece sweatsuit. Even though it's ridiculously comfy, according to reviewers, it'll make you feel put-together during hectic travel days. Best paired with some chunky sneaks.

Yep, October Prime Day is also a great time to give your underwear collection a little refresh. This timeless bralette from Calvin Klein offers support without skimping on comfort, making it the perfect piece to wear beneath sweaters.

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Clearly, I'm a sucker for a cable knit, because this adorable sweater dress also caught my eye. It screams fall in the best way, so I highly suggest wearing it to a pumpkin patch or apple orchard with a pair of suede boots.

Your feel will feel so nice and toasty after slipping into these mini ankle boots, lined in genuine shearling fur. Shoppers love that they feel like slippers, but can be worn outside thanks to their slip-resistant sole.

Headshot of Lauren Gruber
Lauren Gruber
Associate Editor

Lauren Gruber is an associate commerce editor at Hearst Magazines, where she writes for publications like Good Housekeeping, Cosmopolitan, Prevention, Country Living, House Beautiful, and more. She has over four years of professional experience covering a variety of lifestyle topics from home to fashion, with an advanced background in beauty and fragrance. When she’s not researching the most worthy Prime Day deals or hands-on testing all the latest perfume launches, Lauren is probably hanging out with her cat Serafina or flexing her AMC A-List membership at the movie theater. 

You can find her previous work at Entertainment Tonight, Shop TODAY, USA Today, Self Magazine, L’Officiel USA, V Magazine, and Modern Luxury Media

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street style lfw september 2025 day two
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