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 12 of our favourite takes on the popular outfit.
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.
Simple, but so effective.
These would elevate so many different outfits.
I love the two handles on this incredibly chic, minimalist bag.
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.
Effortlessly cool, this is a great alternative to the pricier style Annabel is wearing.
The buckle detail gives these biker boots just the right amount of edge.
The winter essential.
Style Notes: Patterned tights are making a comeback this season, and Chrissy shows how to style them in such a sleek way.
The geometric print and high neck gives this mini dress a Sixties feel.
A subtle scattering of polka dots.
Aren’t we all thrilled that kitten heels are trending right now?
This is such a standout coat—and it goes up to a 4XL.
Style Notes: Proof that chunky sole, flat boots can look extremely sophisticated.
This colour is so versatile.
Such a great dupe of those viral earrings.
These cult boots always sell out—grab them while you can.
COS always delivers on sleek, minimalist accessories.
Style Notes: This is such a great look for festive events—and tall boots are the ideal party shoe for dreary December nights.
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.
Style Notes: If you love the silhouette of a shirt dress, you can easily bring it into the winter months by styling it with a classic trench coat and slick ankle boots.
The crinkled pleats and wide cuffs make this look so much more expensive than it’s pricetag.
I love the dramatic collar on this trench—and the fact it’s actually water-repellant.
The Chelsea boot and Western boot crossover I didn’t know I needed until now.
Style Notes: A simple monochromatic look that’s so effective—and demonstrates exactly why riding boots will always be in style.
White dresses always look particularly chic in the winter months when contrasted with black tights.
These boots are up for whatever you have planned.
A pea coat is a style that always looks effortlessly polished.
Style Notes: The electric blue boots really make this look pop, and add a fun touch to an otherwise very proper outfit.
This dress could easily go from day to night.
A pop of colour that would do their namesake proud.
The oversized fit makes it perfect for layering over a knit dress.
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.
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.
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.
I love the silhouette of a sleeveless, turtleneck midi dress.
The embroidered motif give these an authentic Western look.
A leather blazer is an easy way to upgrade any outfit.
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.
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.
This coat would refine any outfit.
Style Notes: I’m saving this for my New Year’s Eve outfit inspo. The contrast of the dress and the high-shine patent leather knee-high boots is perfect for winter celebrations, and I’d add a leather trench for venturing outside.
The velvet and the crystal-embellished box at the bottom of the v-neckline make this such a perfect winter party dress.
These boots are calling out to be your next party plus one.
I cannot stop thinking about this coat—it’s such a cool, minimalist take on the leather trench.
