Leset, Madewell, UGG: This Year’s Best Early October Prime Day Fashion Deals

By , a senior writer at the Strategist covering fashion. She joined the Strategist as a writer in 2021 and before that worked at NBC and HuffPost.

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Photo-Illustration: The Strategist; Photos: Retailers

October Prime Day is returning October 6 and 7, and we’ll be covering all the best deals. To find the best early deals in every category, follow all of our October Prime Day coverage.

Editor’s note: Prime Day has started, so we’re no longer updating this early deals post. You can find all the best Prime Day deals in every category here, and you can find all our Prime Day coverage here.

If you missed out on Prime Day in July, there’s always October Prime Day, officially known as Prime Big Deal Days. The two-day sales event is running from 3:01 a.m. ET on October 6 to 2:59 a.m. ET on October 7, and just like Prime Days past, the deals are starting early. As our senior fashion writer, I’m rounding up the best early Prime Day fashion deals — and so far they look promising. Not only are Levi’s Ribcages 30 percent off right now, you can get a Leset pointelle T-shirt for $78 and Law Roach’s Hanes sweatpants starting at $13. Be sure you sign up for the Strategist Deal Freaks Daily newsletter to get the best Prime Day deals sent to your inbox too — we’re all in deal-hunting mode through next week.

Deals I personally think are the best

Leset Pointelle Slim-Fit Top
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$98

You only get Leset this cheap during Prime Day (and maybe Black Friday).

Loeffler Randall Dina Travel Tote - Black
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$195

There’s a “Mary Poppins situation” inside, with room for a laptop, water bottle, toiletry bag, etc.

Hanes EcoSmart Fleece Jogger Pants
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From $25

The Hanes sweatpants Law Roach can’t live without.

Women’s Deals

Madewell Northside Scoop Tank
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Madewell Northside Scoop Tank

From $18
$25 now 28% off
From $18

Here’s something to layer later.

Free People Latte Blues Thermal Solid
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Leset Pointelle Slim-Fit Top
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Maybe the cheapest Leset pointelle goes for.

Madewell Modal Rib Long-Sleeve Crew Neck
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Madewell Embroidered Bauble Pointelle Stitch Cardigan
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Levi’s Ribcage Full Length
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From $110

Our “Goldilocks of jeans,” available in full length (instead of standard ankle).

Read more: I Designed the Levi’s Ribcage Jeans

Levi’s 318 Shaping Wide-Leg Jeans
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Producer Mbiye Kasonga credits them with getting her back into jeans: “They’re categorized as ‘shaping’ jeans, so they have more give.”

Read more:What Wide-Leg Jeans Is Everyone Wearing These Days?

Madewell The Greta Ballet Flats
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Our senior kitchen and dining writer, Emma Wartzman, wore these mary janes all over SXSW.

Read more:The Flats Report

Hunter Darisa
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Hunter Darisa

From $85
$150 now 43% off
From $85

Hunters for a light-rain kind of day.

UGG Elea Slip-on
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From $130

The late great André Leon Talley once said, “Once you put on an UGG, you never turn back.”

Madewell The Lexie Ankle Boots
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Teva Voya Infinity
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Teva Voya Infinity

From $31
$50 now 38% off
From $31

Plan to spend next summer in Mary-Kate Olsen’s Tevas.

Read more:Mary-Kate Olsen and I Both Own a Pair of Rather Nice-Looking Tevas

Madewell Inez Belt
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Madewell Inez Belt

$70
$78 now 10% off
$70

Swap your regular brown suede belt for a leopard calf-hair one.

Madewell Crochet Knit Bucket Hat
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Loeffler Randall Dina Travel Tote - Black
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“To quote Tom Wambsgans, [it’s] absolutely ludicrously capacious,” says our contributor Katie Stone. Her “personal capacity record” includes a laptop, swimsuit, sauna hat, chargers, toiletry bag, lip balm, hand cream, wallet, pill case, and water bottle.

Read more:I Found the Tote Bag to End All Tote Bags

Men’s Deals

Gap ’90s Loose Heavyweight-Twill Pant
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From $45

Take a well-earned break from chinos.

Levi’s 550 Relaxed-Fit Jeans
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Levi’s 550 Relaxed-Fit Jeans

From $52
$75 now 31% off
From $52

There’s extra room in the 550s compared to the 501s.

Hanes EcoSmart Fleece Jogger Pants
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Calvin Klein Cotton Stretch 3-Pack Boxer Brief
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Sperry Authentic Original 2-Eye Boat Shoe
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Vince Grant Suede Loafers
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Vince Grant Suede Loafers

$198
$350 now 43% off
$198

Very The Row–y — and not a whole lot.

Lacoste Rib Knit Brushed Wool Beanie
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From $44

Guaranteed warmth between the ears.

Kids’ Deals

Columbia Youth Steens Mt II Fleece
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The Children’s Place Leggings
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For cartwheels, hopscotching, and other gym-class activities.

UGG Tasman Mule
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UGG Tasman Mule

From $67
$100 now 33% off
From $67

Try the bunny-ears method — without adult supervision.

More Prime Day Deals

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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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