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 2024.
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 2024:
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.
I love the 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. PARTY DRESS + SILVER BOOTS
Style Notes: Metallic boots are making a comeback this season, and Ingrid shows how to style them in such a sleek way for the upcoming party season.
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This has a Sixties feel.
Aren't we all thrilled that metallic heels 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 iconic 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.
Missoma 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 festive events—and tall boots are the ideal party shoe for dreary December 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. POP OF COLOUR DRESS + COWBOY BOOTS
Style Notes: Cowboy boots keep coming back into fashion, and for good reason. They're understatedly cool, and bring an edgy touch to an otherwise soft, cosy look.
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A leather blazer is an easy way to upgrade any outfit.
I love the silhouette of this scarf midi dress.
For a more pared-back Western vibe.
10. PRINTED 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, River Island!
These boots are calling out to be your next event's plus one.
I cannot stop thinking about this coat—it's such a cool, minimalist take on the leather trench.
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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