What Do I Wear? 4 Outfits For Hard-To-Dress-For Winter Scenarios

It seems as though any time the temperature dips below 50 degrees, the simple act of getting dressed becomes a months-long battle between looking good versus staying warm. Do I want to spend the evening shivering in a too-thin, seasonally inappropriate dress that garners an onslaught of compliments? Or do I want to pile on everything I own and become a Joey? 

Throw in a situation, like the first holiday fête you’ve been invited to in years, and the whole thing feels exponentially difficult to navigate. But don’t stress: Aesthetics and warmth don’t need to be opposing forces nor are they mutually exclusive. With the right layers, brought to you by Cuddl Duds, every hard-to-dress-for winter scenario is all at once very achievable. We pinpointed four such instances, from dining outside to first-date hikes, and pieced together the outfits that do it all. Click through to shop our winter outfit ideas, ahead.

Scenario: You still don’t feel comfortable dining indoors, but you feel bad canceling plans with friends again. It’s about 27 degrees outside (and that’s without wind chill), and no matter how strong or state-of-the-art the outdoor heater is, you know you’ll freeze by the time your entree is served. 

What To Wear: The goal here is insulation, and the key to warmth is to double up on everything. Start with a fleece-lined base (a long-sleeve crew and leggings) and pile on a darling cardigan, roomy white wide-leg jeans (perfect for layering), and a puffer.

Cuddl Duds Fleecewear with Stretch Long Sleeve Crew Neck Top, $, available at QVC

Cuddl Duds Fleecewear Stretch Leggings, $, available at QVC

Ganni Poplin Collar Cardigan, $, available at Ganni

Frame Le Italien Wide Crop Blanc, $, available at Frame

Banana Republic Plaid Water-Repellent Long Puffer Coat, $, available at Banana Republic

Loq Georgia Boot, $, available at LoQ

Scenario: Your office is throwing its first holiday fête in two years and as much as you want to roll up cocooned in something equivalent to a sleeping bag (because you basically hibernated all of last winter), you know you have to look at least somewhat decent in front of your colleagues.

What To Wear: It’s all about strategic layering with first, a foundation of base layers that promise to retain body heat without adding bulk. Opt for a knit dress as opposed to a cotton or satin number that’ll do nothing against a cold forecast. And to finish, a super-sleek camel coat and a pair of over-the-knee boots for another layer of insulation. 


Cuddl Duds Softwear with Stretch Long Sleeve Crew, $, available at QVC

Cuddl Duds Softwear with Stretch Legging, $, available at QVC

Zara Wool Blend Knit Dress, $, available at Zara

Toteme Belted wool coat, $, available at Net-A-Porter

Jordan Road Emma Hoops Medium, $, available at Jordan Road

Nomasei Black Over-the-Knee Boots, $, available at Nomasei

Scenario: You can’t remember the last time you were this excited about a first date with someone you matched on a dating app, but much to your chagrin, they suggest a leisurely hike...in the winter.

What To Wear: A leisurely hike means you can forego the hardcore, not-so-cute winter gear (which is fine for, like, the 50th date). Slip into a pair of plush velour leggings and a pretty floral-laden turtleneck as your base, and to ensure maximum warmth, layer up on a fleece pullover, which allows your turtleneck to peek through.


See By Chloé Eilieen Shearling-lined Ankle Boots, $, available at Net-A-Porter

Dauphinette Chinoiserie Sophia Turtleneck, $, available at Dauphinette

Cuddl Duds Soft Terry Anklet Lounge Socks Set of Three, $, available at QVC

Cuddl Duds Double Plush Velour Leggings, $, available at QVC

Cuddl Duds Fleecewear with Stretch Mixed Media Top, $, available at QVC

Telfar Embroidered Beanie, $, available at Telfar

Scenario: You absolutely adore your nieces and nephews but they have boundless energy and all they want to do is spend hours outdoors building snowmen and making snow angels. 

What To Wear: Brace for the cold and the inevitable soaked-through outfit by layering a thermal set underneath a sweatsuit (perfect for peeling off afterward once you’re back inside). Finish the look with a puffer, sherpa-lined socks, and waterproof footwear. 


SOREL Women's Kinetic™ Caribou Boot, $, available at SOREL

Carhartt Knit Beanie, $, available at Carhartt

Thakoon Brushed Sweatpants, $, available at Thakoon

Thakoon Drawstring Hoodie, $, available at Thakoon

Cuddl Duds Faux Sherpa Cozy Lined Socks Set of 2, $, available at QVC

Cuddl Duds Stretch Waffle Legging, $, available at QVC

Cuddl Duds Ladies Stretch Waffle Long Sleeve Top, $, available at QVC

Cuddl Duds Comfy Soft Puffer, $, available at Cuddl Duds

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