As the nights draw in and temperatures start to drop, it’s fair to say that cosy season is upon us, and with that comes one of our favourite footwear pairings: dresses and boots.
An easy outfit combination for those cooler months, knowing how to wear boots with dresses is an essential wardrobe skill at this time of year. Whether you’re looking for the sophistication of a simple Chelsea boot or the wow factor of some over-the-knee showstoppers, we’ve pulled together ten of our best boots to wear with dresses that’ll have you covered for every occasion on your social calendar.
1. Chunky boots and dresses for extra attitude
Let’s face it. Fashion doesn’t always go our way in terms of delivering both style and comfort; but when it comes to the chunky boot, it has both bases covered! A thick, sturdy sole provides amazing foot support and good grip for those frosty mornings, while the chunky silhouette means you can throw them on with anything and look perfectly put-together.
If you’re in the market for a new pair of black boots to wear with dresses, these Rocket Dog Dekko boots have been a favourite of ours this season. Try teaming your chunky boots with a floaty maxi dress for just enough balance between girly and grunge, or pair with a leather pinafore and black tights for an edgier look.
2. Knee-high boots and dresses for autumn chic
Knee-high boots and dresses are a match made in heaven. Wear them with a mini dress, and they create a flattering look that accentuates your legs, but pair them with a midi dress, and you’ll look like you’ve walked straight off the runway!
These Riva Nowra knee-highs have the versatility your wardrobe needs this season. The lightweight block heel and inside zip make for comfortable wear, and the rich, chestnut-brown leather pairs perfectly with warm-toned dresses. Offering comfort, style and sophistication, what more could you want from a pair of boots?
3. Doc Martens and dresses for a cult-classic look
The original boot that embodies nineties grunge has come back with a vengeance in recent years – and it’s easy to see why. Their classic lace-up style, yellow stitch detailing and reputation for long-lasting quality make them a great addition to any shoe rack. Plus, Dr. Martens are arguably the best ankle boots for pairing with dresses.
These Dr. Martens 1460 Smooth boots have an eight-eyelet lace-up fastening, leather upper and lining, and the brand’s infamous air-cushioned outsole. Don them with some patterned tights and a denim dress for the ultimate nineties look, or pair with a floral midi dress for added edge.
4. Chelsea boots and dresses for casual comfort
Chelsea boots and dresses have been fashion friends for a while now. Their classic, laid-back style make them an easy pair to throw on with your dress of choice – and these S.Oliver Stomp Chelsea boots are no different. A chunky, cleated sole offers plenty of protection from winter weather, while a neutral, faux-suede upper makes them an unbeatable choice for any dress and boots outfit.
Try teaming these booties with a shirt dress and oversized blazer for office chic, or keep things casual with some chunky-knit socks for added warmth.
5. Long, over-the-knee boots and dresses for a serious statement
Now, here are a pair of boots that really make a statement. The Linzi Rachel over-the knee boots are the perfect accompaniment to that Christmas party dress you’re struggling to know what to wear with. The soft, black-suede material and long, thigh-skimming silhouette are the epitome of glamour. Pair them with a sequined mini dress for an outfit fit for a disco queen, or style with your favourite LBD for a sophisticated look that won’t date.
Either way, you’ll be the envy of everyone at the party.
6. Biker boots and dresses for added grunge
Another classic pair of flat boots to wear with dresses, biker boots are an on-trend choice if you’re looking to upgrade this year’s boot collection. Perfect for balancing out ultra-feminine dresses with a more masculine, grungy vibe, they can turn an outfit from ‘meh’ to ‘yeah’ in a matter of seconds. Our Linzi Leader black biker boots could be just the pair for you. With gold buckle detailing, eyelets and studs, these punk-rock style cues will give that floral maxi at the back of your wardrobe a new lease of life.
7. White boots and dresses for cool-girl chic
Easy to pair with all types of dresses and a style seen gracing the feet of many a Kardashian in recent months, a heeled sock boot is this season’s must-have item. The simple, slip-on shape is given a revamp with our Linzi Nala heeled boots in ivory faux leather. Perfect for those meetings where you want to make a statement or those festive drinks where you’re dressing to impress, these boots promise to pair beautifully with any dress in your wardrobe.
8. Ankle boots and dresses for everyday effortlessness
Prefer a little added height, but without the pain that comes with high heels? These low, chunky-soled ankle boots could be just what the doctor (or podiatrist!) ordered. Minimalist yet stylish, these stunning Divaz Taijal Chelsea boots in tan-coloured vegan leather are the best to wear with dresses. Slip on some chunky socks and an oversized knit dress for an effortless look that’s ready for anything, ranging from nipping to the supermarket for a loaf of bread to a smart-casual dinner out with friends.
9. Suede boots and dresses for classic style
Soft suede, delicate buckles and elegant gold detailing; what’s not to love about the Jenna boots from Hush Puppies? If you think they look good on the outside, wait until you hear what’s on the inside. Featuring a cosy fleece lining and a cushion-comfort, memory-foam leather insole, these boots are like a hug for your feet. Pair with a burgundy pleated dress for autumnal sophistication, or a jumper dress and tights for a warm outfit on days where extra layers are necessary.
10. Cream boots and dresses for a photo-worthy outfit
Cream-coloured boots are having a real moment in the spotlight – and we’re totally okay with it! Granted, they may not be the most practical colour for a rainy day in winter, but our faux-leather Linzi Trooper Chelsea boots in beige are just too gorgeous to not shout out. Easily wiped clean on those days where the puddles have got the better of you, these neutral boots will take any dress you choose up a level in the style stakes.
Pair these nude beauties with an all-neutral outfit for an effortless look to envy the Instagram stars, or team with a dark floral maxi for a seasonal statement look.
Hopefully, our roundup has given you some inspiration on how to wear boots with dresses this season. Whether you’re looking for a pair of heeled boots to suit your new maxi dress for date night, or you’re simply after some ankle boots to wear with your favourite midi dress, find the latest styles at affordable prices online or in-store!
