Yellow dress with black boots for Women by HUGO Yellow dress with black boots for Women by HUGO

Combining dresses
with boots:
the best styling tips

Combat boots, cowboy boots, calf-length boots, and ankle boots – with a whole range of different styles, boots never go out of season. They’re a classic companion to trousers, but they also pair nicely with dresses. From long, flowing maxi dresses to elegant mini dresses, you’re free to experiment with an assortment of different styles.



But all these possibilities just makes it harder to settle on the right outfit. That’s why we’ve put together this guide on combining dresses and boots, so you can always master the perfect outfit for every season. Whether you prefer a midi dress with boots or a shorter dress with ankle boots and tights, let the following looks inspire you to create wonderful styles!

Boots and dresses: styles for every season

Dresses of all types pair well with boots, giving you endless flexibility when selecting your outfit combination. Whether you pick a light summer dress with boots or you need a warmer winter dress with boots, every season is dress and boots season! For more inspiration on how to wear boots with dresses in each season, check out the following style tips.







The question of “which dress and boots outfit should I wear for the summer?” doesn’t have a clear answer. Instead, you can choose between a whole host of different styles, materials, and colours. That said, lighter colours and materials are best for the summer months, since they’re often much more comfortable and radiant on brighter days. Wearing ankle boots with a long dress, for instance, makes the ideal lightweight summer outfit.



Want an edgy look that’ll turn heads wherever you go? A boho-style summer outfit is perfect for you! Pick a long, flowing maxi dress with boots that complement your clothes’ light colours – whites, beiges, and browns are best – and round your outfit off with a long necklace, large sunglasses, and a western-style hat for a truly trendy look.



For a summer night out, buckled boots and a sequin dress are a classic combo. Platform shoes are also making a comeback in the fashion world and can add that extra layer of extravagance to your outfit. Even if it’s just a simple summer dress with tights and boots, every dress and boots outfit can be put together quickly and effortlessly – leaving you more time to enjoy your evening.







Boots continue to shine even when the sun doesn’t. In colder months, boots are equally as eye-catching as they are frost-defying, keeping your legs nice and warm while they work their magic as a fashion statement. Combine flat Chelsea boots with a knee-length dress for a perfect cold weather outfit. Adding a cashmere beanie and a coat over the top completes your winter look.



If you’re braving the weather and wearing a short dress, over-the-knee boots make the best addition to provide a bit more warmth. If you’re a hardy Brit and don’t fear the cold, you can leave a gap between where your dress ends and the boots begin to flash a little skin. Alternatively, ankle boots go incredibly well with a bodycon dress, while studded boots make a great companion to mini dresses.



Calf-length boots also work well with knitted dresses. Combine them with tights or stockings in matching colours for a uniquely autumnal outfit. Who says a short dress with boots can’t keep you warm? With our styling tips, you can look good and feel cosy all year round!

Black dress and boots for Women by HUGO Black dress and boots for Women by HUGO

Enhance your outfit with added accessories

Even a well-considered dress and boots outfit isn’t complete without a little something extra. To really refine your looks, check out the following styling tips for how to pair high-quality accessories with your dress and boots combo:





The type of jewellery you should add depends on your dress. If strapless, always remember that less is more. If you’re sporting a square neckline, a choker or collared necklace is best. And for patterned summer dresses, thin necklaces with modest pendants are the most flattering.



Hats & Caps

For casual and sportier looks, try adding a baseball cap to a midi dress with boots or pairing a summer dress and boots with a Panama hat. Wide-brimmed hats are great for warmer months, while knitted and woollen hats are perfect for the autumn and winter.




It’s very important you choose a bag that matches your outfit’s tones, particularly if your boots pop with a bright colour. A clutch works well for formal occasions, elegantly complementing a nice party dress with ankle boots. For sunny days outdoors, however, a small backpack can really enhance your look.

Pink belted dress with black boots for Women by HUGO Pink belted dress with black boots for Women by HUGO

Outfits with a dress and boots offer a variety of styling options

From busy office days to leisurely weekends, eventful nights out to long journeys abroad, there are so many suitable occasions to wear a dress and boots outfit. Here are some ideas on how to adapt your look to fit whatever situation you find yourself in:




Outfits that combine a dress with boots are absolutely appropriate for the office, particularly in the colder months where calf-length boots are ideal for warmth. Your overall dress code will depend on your company’s culture, but neutral colours like blacks and dark browns are always safe choices. For casual Fridays, brighter colours like burgundy and scarlet also work.




Leisurely strolls in the park or shopping sprees around town are the ideal occasions to flaunt a dress with boots. Flat ankle boots are very popular since they’re so versatile and make your legs look longer. Chelsea boots are especially beloved due to their comfort and the fact that they can be combined with just about anything. A knee-length dress and Chelsea boots make the ideal leisure outfit.




Wearing a dress with boots is the perfect combination when travelling, not least because it keeps you cool and comfortable on long train or plane journeys. If you’re packing your outfit in your suitcase, make sure to choose a soft and wrinkle-free piece. That way, it will survive the trip in good condition, and you won’t have to spend time ironing while on holiday.

You can go as daring as you like with your boots but remember to take note of the temperatures of your destination. Be sure to choose the ideal combination of comfort and style, especially if you are going to be doing a lot of walking. That said, flat boots make the ideal footwear for long holiday treks.