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.
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