January 22, 2025

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Fashion Trends, Shopping More Joyfully

47 of the Best Deals

47 of the Best Deals

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Cyber Monday is officially here, and we’ve scouted the best deals, including some of our favorite styles at their best prices of the year.

Some brands have extended their Black Friday discounts through Cyber Monday, while others have increased their savings or added new items to their sales to keep shoppers engaged. First, Everlane’s Cyber Monday sale is still running, meaning nearly everything is up to 50% off. Madewell is also going strong with 50% off (again, nearly) everything.

Either way, you won’t want to wait much longer to shop, as many of the best items are beginning to sell out. So, let’s get to it: here are the best Cyber Monday sales and deals on clothes, shoes, bags, and other accessories for building a complete winter wardrobe.

The best Cyber Monday shoe deals

When you shop for shoes from department stores like Nordstrom or Zappos, you’ll find a daily rotation of new styles leading up to Black Friday. We’ve also scouted comfortable walking shoes, cozy clogs, and a discount on some of the best flats we’ve tested. If you see your size and favorite color are still in stock, don’t hesitate.

Brown suede clog

UGG New Heights Clog

The New Heights suede clogs are a prime example of “cottagecore” fall fashion. On the inside is a microfiber sock liner, so you can dress them up with tube socks or wear them barefoot.

Mia Inez

Inez Mia

As a style editor, believe me when I tell you that Inez is one of my absolute favorite brands for shoes that are miraculously comfortable and completely stunning. Seriously, I don’t know how they do it — but I do know that these slingbacks are some of their best work when it comes to style and comfort.

Boot

Madewell The Zane Knee-High Boot in Leather

These sophisticated leather boots are well-suited for nearly any occasion, be it a trip to the office or a night out with friends. The 2.5-inch stacked heel adds a nice boost in height—that is, without needing to sacrifice on comfort.

Mary Janes

Rothy’s The Point Mary Jane II

“These are a major upgrade compared to Rothy’s original Mary Janes,” says Gabrielle. “The strap is now more refined and the pointed toe box feels a bit roomier.”

Flats

Allbirds Tree Breezers

These pliable flats come in less colors than Rothy’s, but still beat them in terms of comfort. They have sneaker-like support in their footbeds and take zero break-in time.

Margaux The Heel

Margaux The Heel

The Margaux Heel is a favorite because it’s a block heel that’s minimal and pairs well with skirts, denim and dresses, They’re the type of heel you go for when stillettos aren’t you’re go to choice of shoe.

Ballet flat

Madewell The Greta Ballet Flat

If you want to see a comment section full of enthusiasm and exclamation points, check out the hundreds of reviews for these flats. Hailed as comfortable and versatile by both narrow-footed and wide-footed people alike, these flats could be the shoe you’ve been searching for.

Brown boots

Inez Paloma

“The heel height, pitch, and wide-calf fit, and option for a wide footbed make everything about the boot super comfortable when you’re standing still or walking,” says executive editor Sally Kaplan.

Sneaker

Allbirds Women’s Couriers

These retro-inspired sneakers are made with responsibly sourced, high-quality materials, creatively crafted into a pair of walking shoes that you can wash and wear for the seasons ahead.

Allbirds Women's Tree Runners in Bloom pink.

Allbirds Women’s Tree Runners

Allbirds Women’s Tree Runner sneakers are crazy comfortable with a flattering and close-fitting silhouette and have a smooth but texturized upper.

Women's Wool Runner

Allbirds Women’s Wool Runner Go

Renamed the Wool Runner Go, these are Allbirds’ most popular shoes. With a comfortable wool upper and sugarcane midsoles, they’re designed for casual wear.

The best Cyber Monday handbag deals

For all the purse girls who aim to save whatever money fits in their handbag, Black Friday is a prime opportunity to find rare Black Friday Coach deals. A more affordable alternative among our favorite purse brands is JW Pei, now marked down to the same degree we saw on Prime Day.

Over at Madewell, there’s 40% off leather crossbody bags when you use the code “MADEBETTER.” Check our guide to the best Madewell Black Friday deals to keep up with how the discounts evolve throughout the week.

Baby Bogg Bag

Bogg Bag Baby Bogg Bag

“I tried the Baby Bogg first when we had a school picnic. Its size was perfect for water bottles and snacks, and its smaller design made it look less like a beach bag,” writes deputy editor and mom-of-three Conz Preti.

Coach Women's Soft Tabby Shoulder Bag

Coach Soft Tabby Shoulder Bag

This denim-and-gold-accented Tabby in the large size is a modern revival of a 1970s design. It can be worn as a shoulder bag, a crossbody, or a top-handle bag.

White purse

Lo & Sons The Aoyama

“The vertical side pocket means I never have to swing it off my shoulder to root around for my phone,” says associate style editor Gabrielle Chase about this four-in-one bag.

JW Pei Women's Carly Saddle Bag on a white background.

JW Pei Women’s Carly Saddle Bag

From one of our favorite purse brands, the JW Pei Women’s Carly Saddle Bag is made of vegan leather and comes in over a dozen colors, so you’re sure to find an option that complements your favorite outfits.

Bucket tote

Madewell The Essential Bucket Tote

Beloved by style mavens and celebrities alike, this roomy bucket bag combines functionality and style with savvy features like a magnetic closure, interior pocket, and adjustable shoulder strap. Choose from eight chic hues, and for an extra-personal touch, opt to have yours monogrammed.

Our favorite cashmere on sale, plus the top knitwear deals

As our resident cashmere enthusiast (everyone else on the team is allergic) I’ve tested a lot of sweaters, from entry-level to luxury grade. Still, the brand that impressed me the most for its price point is Naadam. The Naadam Black Friday sale currently has supremely soft knits for 40% off, but this could go up to 50% off once Black Friday is officially on.

Another hot spot for cashmere, Jenni Kayne’s Black Friday event now has 25% off everything, from her coveted preppy-chic apparel to an array of elegant West Coast-inspired furniture. I tried the Cropped Cocoon Cardigan myself, and it really does feel “cloud-soft.”

Sweater

Madewell Cashmere Relaxed Crewneck Sweater

Despite how lightweight it looks and feels, this sweater offers plenty of warmth and comfort thanks to its luxe cashmere construction. The ribbed trim adds an extra-chic touch, while the relaxed fit makes it suitable for everyday wear.

Sweater

Everlane The Square Neck in Cashmere

This slim-fitting, slightly cropped sweater is made from recycled cashmere. It comes in black or a very pretty pale pink and has a flattering scoop neckline.

Cyber Monday sales on jeans, work pants, and comfortable bottoms

Wide-leg jeans are the pants of the moment. You’ll see them styled with sneakers, flats, or loafers — without fail, they look cool. Our top overall choice we tested is The OG Baggy Jean, which is 50% off during Everlane’s Black Friday sale. For premium stretchy work pants, see our guide to the best Spanx Black Friday deals.

Pants

Everlane The Dream Pant

This double-knit fabric has a flat finish, so it looks polished but is still comfortable enough to nap in. The stretchy fabric and elastic waistband are unbelievably comfortable and wrinkle-proof, while the pintuck detail keeps them smart.

Hi-Rise Flare

Spanx PerfectFit Ponte Flare Pant

The material is a comfortable, versatile, and machine-washable Ponte fabric that’s smoothing but not constricting, similar to yoga pants. They come in petite, regular, and tall lengths in sizes XS – 3X.

Everlane The Baggy Jean

Everlane The OG Baggy Jean

Baggy jeans are back. We love Everlane’s iteration with its roomy waist and wide leg for a comfy, loose fit.

Low-Slung Baggy Jeans

Madewell Low-Slung Baggy Jeans

We’re in a trend cycle of dropping waistlines and less structure — and these are the jeans that epitomize our current aesthetic.

Skirt

Madewell Utility Mini Skirt in Moleskin

This effortlessly cool mini skirt stands out for its functional cargo pockets and stretchy cotton moleskin fabric—and it looks equally great paired with a graphic tee or sweater as it does with a blouse and tights.

The best Black Friday coat and jacket deals

Between parkas and puffers from brands like The North Face, your going-out look needs something with a longline silhouette that complements what’s underneath and keeps out the cold. For this, we’re scouting heavyweight wool blends from Cole Haan, Kenneth Cole, and the like from Saks Off Fifth, where you can take an extra 50% off outerwear with the code “HOLIDAY.”

Puffer jacket

Abercrombie & Fitch Ultra Puffer

“I’ve been buying Abercrombie & Fitch winter coats for years, and I’ve never been disappointed in a purchase,” says freelance writer Talia Ergas. “The Ultra Puffer turned out to be everything I hoped for. The puffiness is balanced nicely by the short silhouette and luxurious faux fur accents. I also love that the bottom hem is elastic, so it hugs my hips and keeps the cold out.”

Frank and Oak

Frank and Oak Capital Parka

Fully waterproof and seam-sealed, this jacket is fortified with vegan PrimaLoft, a fleece-lined collar to prevent chafing, waist adjustment, and even a media pocket inside with a headphone cord hole.

Camel coat

Madewell The Alonzo Coat

This alpaca-wool blend longline top coat is a weighty, substantial outer layer for cold-weather commutes.

Black Friday Pajama deals

The holidays are the perfect time to cozy up in a great pair of pajamas. We test pajamas year-round and have done lots of research into brands that are endlessly cozy and actually keep their coziness in the wash. We have a big roundup of all the best Black Friday pajama deals, but here are some of our favorites.

Women's Pima Shorts Set

LAKE Women’s Pima Shorts Set

A scoop neck, short sleeve top and dolphin hem, elastic waistband shorts are the perfect pair for a luxurious night of sleep.

Shopping for more discounts today? Check out our roundup of all of the best Cyber Monday deals.


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