An Editor Tried on Amazon’s Winter Fashion IRL

I’m the first to admit that I used to be a bit of a snob about buying clothes from Amazon. Of course, I’ve always relied on the retailer to restock my beauty essentials, cat food, and the seltzer that I drink religiously, but I tended to steer clear of the fashion section. However, in the past year or so, it’s come to my attention that I had no idea what I was missing—Amazon carries a seemingly endless amount of trend-forward pieces and high-end brands. Plus, you still get the same fast shipping and easy returns that making shopping there such a pleasant experience.

Recently, I had the opportunity to spend two hours trying on a huge assortment of Amazon’s winter and holiday fashion IRL. And even though my eyes have been opened to Amazon’s stylish selection for a while now, I was still surprised by how many chic, elevated outfits I found—just in time for New Year’s Eve. Below, I’m breaking down five head-to-toe winter looks from Amazon for any and every celebration. Keep scrolling to shop my 12 editor-approved picks from Levi’s, Sam Edelman, and Free People.   

12 Editor-Approved Amazon Winter Fashion

• Festive Print: Z Supply North Sea Fair Isle Cardigan, $120
• Iconic for a Reason: Levi’s 501 Original Fit Jeans, $69 (Originally $98)
• ASTR the Label Doria Corduroy Skirt, $69 (Originally $98)
• Available in Wide-Calf Sizing: Sam Edelman Sylvia Boots, $200
• ASTR the Label Bellmere Jacket, $168
• Butt-Lifiting Bottoms: DL1961 Bridget Bootcut High-Rise Instasculpt Corduroy Pants, $117 (Originally $239)
• The Perfect LBD: Amanda Uprichard Benedict Dress, $233 
• Bailey Rose Leopard Faux Fur Coat, $155
• Sam Edelman Wyatt Boots, $220
• Free People Tigre Printed Mini Dress, $76 (Originally $128)
• [BlankNYC] Night Life Faux Fur Jacket, $98

Z Supply North Sea Fair Isle Cardigan

For my first look, I opted for a cozy, casual Après ski vibe inspired by this Z Supply North Sea Fair Isle Cardigan. Between the soft, chunky knit, alpine print, and icy color palette, it’s the perfect winter sweater.  

Levi’s 501 Original Fit Jeans

I paired the above sweater with a classic staple: Levi’s iconic 501 Original Fit Jeans in a light distressed wash. I can envision myself wearing this comfy-cute outfit to watch the ball drop with my friends.

ASTR the Label Doria Corduroy Skirt

The ASTR the Label Doria Corduroy Skirt was one of my favorite things I tried on because it’s the kind of versatile piece that would look great with pretty much anything. I paired it with an ivory mock-neck sweater, but you could even style it with an oversized rugby or flannel. There’s also a matching blazer if you want to wear it as a set.  

Sam Edelman Sylvia Boots

I love the retro-inspired pairing of a mini skirt and tall boots, so these brown Sam Edelman boots were a no-brainer. The low heel ensures comfort, and they even come in wide-calf sizing to guarantee the perfect fit.  

ASTR the Label Bellmere Jacket

Moving in a slightly dressier direction, I was drawn to the polished vibe of this collarless tailored jacket in a brown houndstooth print. It has padded shoulders and cinches subtly at the waist to create a flattering silhouette. 

DL1961 Bridget Bootcut High-Rise Instasculpt Corduroy Pants

The houndstooth jacket has a matching mini skirt, but it also looked so chic with these stretchy, sculpting corduroy pants in a leg-elongating bootcut style. Bonus: You can snag them for their lowest price in 30 days right now.

Amanda Uprichard Benedict Dress

I couldn’t resist the opportunity to try on festive party outfits, starting with this Amanda Uprichard little black dress. Between the sheen of the taffeta fabric and the effortless shift silhouette, this mini dress is all about understated elegance. 

Sam Edelman Wyatt Boots

Again, a mini skirt or dress with tall boots is one of my favorite outfit formulas, so I gravitated toward these knee-high black boots with Western details. However, I love the idea of styling the Benedict Dress with sheer black tights and a statement heel, like metallic Mary Janes.   

Bailey Rose Leopard Faux Fur Coat

A style maximalist through and through, I had to add a bit of flair to my all-black ‘fit with the Bailey Rose Leopard Faux Fur Coat. I can also envision myself throwing this on with baggy jeans and ballet flats for a grungey everyday look. 

Free People Tigre Printed Mini Dress

Polka dots were everywhere this summer, but the Free People Tigre Printed Mini Dress proves that they’re here to stay through the winter, too. As someone who’s perpetually cold, I appreciate the long sleeves of this statement-making style. 

[BlankNYC] Night Life Faux Fur Jacket

Last but not least, this ultra-soft faux fur jacket by [BlankNYC] is the solution to staying warm during the winter without ruining your fancy outfit. Compared to an animal print, the black color feels especially elevated and will go with anything, while the cropped length makes it easy to style.