It's the fail-safe winter outfit formula that we all turn to every year: dresses and boots. Comfortable, practical and understatedly cool, this combination never lets you down in the depths of the cold winter months, when you're juggling the desire to stay warm without compromising on style.
But like all good things, it can be difficult to keep it feeling exciting and fresh, especially if find one pairing that you turn to time and time again. Luckily, this season our favourite tastemakers are providing plenty of inspiration for different boot and dress combinations that look effortless, sleek and very 2025.
It seems like this year, there's a plethora of boot styles to choose from. While knee-highs are undoubtedly the silhouette of the season, chunky boots remain a top go-to among the fashion set (especially if you get your hands on The Row's cult pair). And then there are the classics: riding boots and simple black ankle boots will always serve you well. Paired with chunky knit dresses or slick, figure-hugging maxis, these boots can help adapt a simple dress to any situation. Scroll on to discover 11 of our favourite takes on the popular outfit.
11 Fresh Dress and Boots Winter Outfit Ideas For 2025:
1. MAXI DRESS + SUEDE BOOTS
Style Notes: An all-black ensemble always looks chic, but Rosie takes it up a notch by pairing a figure-hugging maxi dress with pointed-toe boots.
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Simple, but so effective.
These would elevate so many different outfits.
There are two handles on this incredibly chic, minimalist bag.
2. KNITTED DRESS + BIKER BOOTS
Style Notes: How cosy does this look? Practical biker boots make this ideal for a day of running around town, but you could easily swap in heeled styles for an evening event.
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Effortlessly cool, this is a great alternative to the pricier style Annabel is wearing.
The buckle detail gives these boots just the right amount of edge.
The winter essential.
3. PATTERN MINI DRESS + SUEDE BOOTS
Style Notes: We're calling it now, tartan will be everywhere in 2025. Make like Julie and pair it with another trending item - suede knee-high boots.
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This has a real eighties feel.
Aren't we all thrilled that suede boots are trending right now?
4. MIDI DRESS + KITTEN-HEEL BOOTS
Style Notes: A simple monochromatic look that's so effective—and Lena demonstrates exactly why kitten boots will always be in style. Try layering your midi dress over a roll-neck knit like Lena has for extra chilly days.
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Black dresses always look particularly chic in the winter months when contrasted with pops of white.
The ultimate layering piece.
These kitten-heel boots are up for whatever you have planned.
A double-breasted coat is a style that always looks effortlessly polished.
5. MAXI JUMPER DRESS + CHUNKY SOLE BOOTS
Style Notes: Proof that chunky sole flat boots can look extremely sophisticated. Love how Isabelle has belted her knit dress and added sleek jewellery.
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This colour is so versatile.
An easy way to made a knit dress feel less bulky.
Azora always delivers on sleek, minimalist accessories.
These cult boots always sell out—grab them while you can.
6. SPARKLY DRESS + BLAZER + TALL BOOTS
Style Notes: This is such a great look for winter events—and tall boots are the ideal party shoe for dreary cold nights.
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This is the ultimate party dress—just imagine how this looks when it catches the light?
Bring a tuxedo touch to this party outfit.
These would work equally well with day looks.
7. BROWN KNIT DRESS + PATENT LEATHER BOOTS
Style Notes: Simplify winter dressing by picking one colour and building your whole outfit around it. While black will always be a reliable go-to, brown is a softer, warmer option that looks impressively elegant.
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A deliciously rich chocolate tone.
They're an investment, but they look so, so good.
The contrast of the brown suede with the patent leather would really make this look.
8. MINI DRESS + OVER-THE-KNEE BOOTS + LONG COAT
Style Notes: Consider this a masterclass in playing with proportions. While the dress may be super short, the floor-sweeping coat and over-the-knee boots mean only a flash of skin is showing, making it a truly versatile outfit that could work for so many situations.
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This coat would refine any outfit.
Such a sleek base layer for so many possible looks.
I love the contrast of the sensual over-the-knee leg with the chunky riding boot sole.
9. SHIRT DRESS + PATENT BOOTS
Style Notes: Patent boots keep coming back into fashion, and for good reason. They're understatedly cool, and bring an edgy touch to an otherwise casual look.
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A leather trench is an easy way to upgrade any outfit.
I love the satin finish of this midi shirt dress.
For some texture.
10. ANIMAL-PRINT DRESS + SLOUCHY BOOTS
Style Notes: I'm saving this for my winter evening outfit inspo. The contrast of the on-trend dress and the classic boots is perfect for winter celebrations, and I'd add a leather trench for venturing outside.
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Well done, Nobody's Child!
These boots are calling out to be your next event's plus one.
I cannot stop thinking about this tote—it's such a cool, minimalist take on the everyday bag.
11. LBD + Tall Black Boots
Style Notes: A mini dress layered over a roll neck is an easy way to make the classic work for cooler months. When temperatures really plummet, simply add 40 or 60 denier tights or some thick long socks to this look.
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Obsessed with this fresh silhouette.
This dress could easily go from day to night.
All about those base layers at this time of year.
So sleek.
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