June 3, 2023

There are a lot of things to enjoy about getting dressed for winter. After all, is there anything quite as satisfying as slipping on a new cashmere jumper or pulling on your favourite pair of boots after an eight-month break? Still, that doesn’t mean dressing for the season doesn’t come without its challenges—especially where going out is concerned.

With diaries filled with everything from dinners with friends and trips to the theatre to low-key work drinks and maybe even some nights that call for serious glamour, assembling outfits to go out in for the colder months is nothing short of an art form. You need to consider your layering strategically, give some thought to your materials, and still work out a way to look cute in doing so. This might sound daunting, but there is a way to achieve the best of both worlds. In fact, I’ve found 11 ways.

For those who like to get dressed up, I’ve found several ways you can do so without the risk of frostbite. Then, there are those who refuse to part with their jeans. Don’t worry—I’ve got you, too. And if you’re anything like me and prefer to keep wrapped up like a toasty burrito, I’ve also pinpointed key looks that’ll allow you to keep your coat on and still look as if you’ve put a considerable amount of time and effort into curating your outfit.

Scroll on to see 11 popular going-out outfits to try this winter.


Winter Going Out Outfits: @claudia_berresford

Style Notes: Blazers are a great addition to any winter going-out outfit, as evidenced by Hannah Lewis, whose oversized style will provide her some shielding from the elements without covering up her incredible Paco Rabanne skirt. 

Shop the look:
Arket Oversized Wool Hopsack Blazer
Oversized Wool Hopsack Blazer

Reiss Tereza White Cotton-Jersey T-Shirt
Tereza White Cotton-Jersey T-Shirt

Paco Rabanne Silver-Tone Star Chain Mini Skirt
Paco Rabanne
Silver-Tone Star Chain Mini Skirt

Next Up: I Live in Dresses, and These Are the 5 Trends I’ll Wear Well Into 2022