25 High-Street Dresses You Can Actually Wear When It's Cold

Winter is hard for dress people. We can relate. At least half of the Who What Wear team fall into that category, and a regular point of discussion as soon as there's a chill in the air is how difficult it becomes to get dressed in the morning. Some dresses are made for wearing in winter. They've got nice thick or knitted material and long sleeves, maybe even a built-in roll-neck. Others you have to work a little harder to bring into the wintry fold, adding tights and a base layer underneath. Others, sadly, just don't work no matter how many layers you throw at them, maybe because the material clings to your opaques or the style or colour just looks too summery against wooly legs. 


(Image credit: @monikh)

Figuring out which dresses fall into which of these categories is time-consuming, as our editor in chief, Hannah Almassi, proved recently in this handy TikTok. It requires a lot of trial, error and effort, which is 100% worth it if it means figuring out which of the summer dresses currently hanging in your closet can be worn right now. But when it comes to investing in new styles, well, that's where we can be of service.

We combed the high street to find the best dresses that look great with tights and base layers to keep you toasty but still feeling like yourself this winter. Our tricks? Look out for knitted fabrics; don't overlook the mini (you can always pair it with knee-high boots); shirt dresses and V-necks always work with roll-necks; and if you're a print lover, opt for those with darker base tones, which will streamline your look and keep it from feeling too summery.

So if you're looking to broaden your winter dress options this month, keep scrolling to find 25 styles that are perfect for wearing during this cold front and throughout the year as you start shedding layers.

Shop High-Street Winter Dresses

Up Next: The 9 Most Expensive-Looking Pieces on the High Street This Week

Emily Dawes
Affiliate Editor

Emily Dawes is the very definition of a fashion multi hyphenate. An editor, stylist and writer with over eleven years’ worth of experience in the industry, Emily is known for her impeccable taste, elegant outfit choices and being able to spot the next big thing in fashion from a mile off. Our readers loyally trust her advice and shopping suggestions; so much so she began her own column documenting the most expensive-looking pieces on the high street, which has become a top-performing piece of content for the Who What Wear brand.

Emily has worked for Who What Wear UK since 2020 in a myriad as roles, spanning from contributing editor and branded content editor. Now, she holds the position of affiliate editor and is responsible for the brand’s overall affiliate strategy, ideation and content execution. Working closely with Who What Wear UK’s affiliate manager, Emily has been instrumental in securing and nourishing brand partnerships, surpassing her goals as standard. Leading the team in tentpole shopping moments including Black Friday and Peak Trading, with Emily’s guidance and leadership, team Who What Wear is in a stronger affiliate position than ever before.

Prior to joining the Who What Wear team, Emily served as YOU Magazine’s acting fashion editor where she managed the fashion team and oversaw all fashion content output for the fast-paced weekly title. Emily is a stylist in her own right, having worked with a slew of VIP clients including writer and television personality, Elizabeth Day, as well as styling and art directing several celebrity cover shoots for glossy print publication, Grazia. Her adept fashion knowledge means brands regularly sought out to work with her as a consultant: previously she has developed marketing and content plans for brands for Cocoon and Edge of Ember. Before entering the industry, Emily obtained a Bachelor of Arts in English and American Studies with International Study from Nottingham University. Fun fact: Emily spent a year studying in America which saw her join a sorority during her time there.

When she’s not working or tracking down the chicest, new-in items to share with our audience, you’ll find Emily bestowing her East London home with her stylish flair, reading everything from the classics to cowboy romance novels and escaping to the country with husband, baby boy and dog, Roo, whenever she can.

Emily is currently on maternity leave.