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
Floral prints feel much more winter-appropriate if they've got a dark base like this one. It will mean black tights don't feel too jarring.
The epitome of a chic winter dress.
This beautiful winter floral dress comes in all sizes up to 26.
No one nails chic minimalism like COS. This V-neck is perfect with a roll-neck.
An easy throw-on dress that just needs some black opaques and your favourite chunky ankle boots.
If you told us this COS dress was designer we'd definitely believe you. The shape and material are so interesting, and you could always add a high-neck layer underneath if needed for extra warmth.
Hands down Arket knitted jumper dresses are the best around.
Although this feels like a wintry print now, you could also throw on some gladiator sandals and a basket bag with it on your next holiday.
This looks super comfy, but the classic navy keeps it feeling polished. Add a waist belt and heeled boots for returning to the office.
Even though this has short sleeves, we think it would still work with a second-skin roll-neck underneath.
This knit dress feels quite smart paired with pointed-toe knee-high boots.
Not all winter dresses must be black. This green one is a showstopper but so comfy. Jigsaw is showing all its dresses styled with roll-necks on site right now to prove how versatile they are.
Long sleeves and a thicker, sturdy leather material means you'll stay warm on top, even if you have your legs out in this mini.
Free People is usually known for its excellent summer dresses, but don't overlook the brand for winter. This sweater maxi is perfect for the weekend with chunky boots.
So cosy paired with tights and knee-high boots. The V-neck would also work well with a roll-neck.
If you love the idea of a knit dress but prefer a flattering wrap-dress shape, this is the perfect compromise.
Pair this timeless staple with black accessories for winter and tan accessories come summer.
Arket always does the best throw-on dresses you can wear everywhere.
Choosing a zebra or leopard style is a great way to incorporate prints into winter outfits.
A leather dress is a winter-wardrobe staple. We'd wear a contrasting cream roll-neck underneath for extra warmth.
The styling here shows how versatile a simple black knit dress can be.
Gingham smock dresses aren't just for summer. This one will look great now with chunky boots as well as chunky sandals come spring.
This could even work for winter weddings.
A great throw-on style to wear with tights and knee-high boots.
The dark print of this will flow seamlessly into black opaques.
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