The Fashion Items to Invest in This Fall and Winter, According to the Experts

From left: Courtesy MyTheresa; Courtesy Net-A-Porter

These standout investment pieces will elevate your cold-weather wardrobe for years to come. 

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What's the one item worth splurging on this not-so-normal winter? Now more than ever we're looking toward items that bring us comfort and joy. That's according to some of our favorite folk in fashion who we asked to pick just one luxurious fashion piece in their wardrobe that they're most looking forward to wearing. 

Related: Fashionable and Functional Women's Sneakers Perfect for Fall

Even though the shows may have looked more different than ever, there's still plenty to be inspired by from the fall 2020 fashion trends that hit the runways earlier this year. And now that the collections have hit stores online, our go-to fashion buyers and stylists have shared their favorite pieces with us. From a chic, elevated twist on puffer jackets by Prada to incredibly soft tie-dyed sweaters and novelty knits that'll stand out on the Zoom calls and a winter take on hi-top sneakers.

Related: The Best Men's Loafers to Wear This Fall

Here, we've rounded up their expert picks for the one item worth splurging on this not-so-normal winter.

Interlocking Rings


Courtesy Bergdorf Goodman

"An interlocking Spinelli mixed metal and stone ring is on the very top of my fall, and forever list. Jewelry is completely non-perishable from a fashion perspective. I can see myself rarely taking this ring off, as it’s casual yet strong, and symbolically I anticipate the metallurgic energy I’m sure it will bring."

—Linda Fargo, Senior Vice President, Women’s Fashion And Store Presentation Director, Bergdorf Goodman

To buy: Bergdorfgoodman.com; $4,200

Padded Leather Blazers


Courtesy Mytheresa

“Puffer jackets are a big trend for the upcoming winter season. They keep you warm and cozy, but with the right style very chic at the same time. This one by Prada is my favorite—it’s super luxe; a cool and very sophisticated version, you could also wear as a blazer."

— Tiffany Hsu, Fashion Buying Director, Mytheresa

To buy: Mytheresa.com; $4,499

Tie-Dyed Sweaters


Courtesy Bergdorf Goodman

"I think we are all going to be wanting things that are comfy and cozy this fall, pieces that both feel and look great, perfect for wearing at home as well as our actual or virtual office. Milan-based Altea has tie-dyed some of their incredibly soft sweaters in beautiful, muted colors, giving the 70’s style technique an elegant twist. As the days grow shorter we can certainly appreciate bringing a bit more color in our lives." 

— Bruce Pask, Men's Fashion Director, Bergdorf Goodman

To buy: Bergdorfgoodman.com; $795

High-Top Sneakers


Courtesy Farfetch

“I’d have to confess that fall and winter are my least favorite seasons. But this year I’ve been coveting an older but classic style, Rick Owens Geobasket sneakers. I always go for comfort and these have the comfort of a sneaker but look of winter-ready boots”

—Peju Famojure, Celebrity Stylist 

To buy: Farfetch.com; $697

Novelty Knits


Courtesy Shopbop

"This season is all about head-to-toe knitwear, as it is both practical and comfortable. Lately, I am especially loving novelty when it comes to knits, which makes for the perfect video conference outfit!"

—Caroline Maguire, Fashion Director, Shopbop

To buy: Shopbop.com; $955
To buy: Shopbop.com; $545

Ribbed Knit Dresses


Courtesy Net-A-Porter

"Given the new normal that we are entering this winter, I am looking for pieces with versatility. This ribbed knit dress by Bottega Veneta is fashion-forward, but functional and can be styled in multiple ways; with sheer tights, a roll-neck layered underneath, and a combat boot. It can easily be transitioned into evening by switching it up with a naked sandal. The leather trim details and gold hardware buttons make it extra special and right now, anything by Daniel Lee feels like a true investment piece."

— Libby Page. Senior Fashion Market Editor, Net-a-Porter

To buy: Net-a-porter.com; $3,270