Skip to main contentSkip to footer
Digital Cover hfm© Kirstin Sinclair

How to style dresses with boots this season

Check out our dress & boots outfit combinations this season...

When you purchase through links on our site, we may earn commission. Read our full commerce guidelines here.

Chloe Gallacher
Style Writer
Updated: August 27, 2024
Share this:

There's a time and a place for every conceivable outfit, and rest assured, we like to experiment with the best of them. But for instant, no-thought-necessary polish, a chic dress styled with boots is the winning formula.

 The all-encompassing appeal of a dress erases the need to faff around with separates, and a stylish pair of boots – I'm personally loving how the street style set have recently adopted the biker boot as their own – delivers on both form and function. 

But which pairings are we looking to recreate this season?

We love the street style coming out of Copenhagen Fashion Week and this matching colour combo© Jeremy Moeller
We love the street style coming out of Copenhagen Fashion Week and this matching colour combo

As Fashion Month descends on us, we're taking inspo from the street style spotted around. The dress and boots outfit combo is a failsafe winner for a transitional wardrobe as summer seems to have gone astray and we head into autumn. We love this brown puffed sleeve mini dress paired with matching coloured cowboy boots. 

We've put together some dress and boot outfit combo ideas to inspire you to embrace the trend.

Shirt Dress With Lace-Up Boots

A shirt dress is a staple in any wardrobe. If you want something a bit different than a crisp white style, opt for a printed iteration. Pair it with a classic chunky lace-up boot and keep accessories simple so it doesn't clash with the print on your dress.

  • DRESS: Leopard Printed Denim Mini Dress, £295.00, Ganni
  • BOOTS: Nari Flat Black Leather Boots With Chain, £1,050.00, Jimmy Choo
  • BAG: The Paris Crossbody, £450.00, DeMellier
  • RING: Molten Wave Stacking Ring, £55.00, Missoma

Sleeveless Knitted Dress With Knee-High Boots

A knitted dress is an essential when it comes to a transitional wardrobe. We'd style a cream maxi dress with a pair of chocolate brown knee-high boots for a tonal look and a great alternative to black. Opt for a matching bag to compliment the boots and we'd add gold earrings to match the gold hardware on the bag for a coherent, polished finish. 

  • DRESS: Róhe Ribbed Cotton-Blend Bouclé Maxi Dress, £340.00, Net-a-Porter
  • BOOTS: Knee-High Leather Boots, £329.00, Arket
  • BAG: Mini Tote du Jour Deep Brown, £445.00, Manu Atelier
  • EARRINGS: Dôme Texture Large Hoops, £178.00, Mejuri

Boho Dress With Chelsea Boots

As we all know, the boho trend is back with a bang. We love this Chloé-esque mini dress from high-street favourite store Mango. To keep up with the modern update its having, we'd style with a trusty chelsea boot and and oversized pendant necklace. You can't ever go wrong with a pair of sunnies, so add them to finish off your look.

  • DRESS: Puff-Sleeved Embroidered Dress, £40.99, Mango
  • BOOTS: Thea Leather Chelsea Boots, £198.00, Reiss
  • NECKLACE: Singh Necklace, £95.00, Daphine
  • SUNGLASSES: Celine Eyewear Triomphe Oval-Frame Tortoiseshell Acetate Sunglasses, £400.00, Net-a-Porter

Denim Dress With Cowboy Boots

We love a denim dress and its a great piece to have in your capsule wardrobe. To mix it up to the usual gladiator sandal in the summer, style it with a cowboy boot for the transitional season. To embrace the coastal cowgirl trend, add a tan bag and a neck scarf - if you don't fancy it around your neck, add it to your hair instead. 

  • DRESS: Denim Mini Dress, £45.99, Zara
  • BOOTS: Heritage R Toe StretchFit Western Boot, £160.00, Ariat
  • BAG: Large Leather Shoulder Bag, £195.00, & Other Stories
  • SCARF: Precious Paradise Twilly, £185.00, Hermés 

Knitted Dress With Knee-High Boots

A failsafe option is to go for a simple knitted dress and style it with black knee-high boots. This allows you to ease yourself into the outfit combo to see if it's for you and your style, and is a sleek, effortless look. A classic black knitted dress will go with so much in your wardrobe, as will a black knee-high boot - so just combine them for a put-together look. Incorporate colour into your look through your accessories.

  • DRESS: Staud Obsidian Open-Back Ribbed-Knit Turtleneck Maxi Dress, £475.00, Net-a-Porter
  • BOOTS: Knee-High Boots, £44.99, H&M
  • BAG: Miu Miu Matelassé Logo-Plaque Leather Bag, £2,200.00, Selfridges
  • NECKLACE: 1990s Vintage Monet Ball Necklace, £225.00, Susan Caplan

How we chose: 

  • Style and versatility: All our dress picks feature a flattering silhouette and work harmoniously with the boots we've suggested. When combing through the internet's top fashion sites for the best pieces, we made sure that each of our outfit combinations either felt trend-relevant or timeless for maximum wearability. 
  • Price: Whether you're planning on splashing out or bagging a bargain, we've got a dress in your price range. We've selected this season's best, ranging from high-street brands to luxe designer labels.

Why you should trust me:

I am Hello! Fashion’s Style Writer, with seven years of experience within the fashion journalism industry. I have a love for fashion and spotting upcoming trends, coveted pieces and scouring online for irresistible new-in finds. Finding luxe-looking pieces on the high street is my forte and I love finding those hidden gems that look so much more expensive than they are. 

HELLO!'s selection is editorial and independently chosen – we only feature items our editors love and approve of. HELLO! may collect a share of sales or other compensation from the links on this page. To find out more visit our FAQ page.

Sign up to HELLO! Fashion for style tips, cultural insights, must-have items, and more

By entering your details, you are agreeing to HELLO! Magazine User Data Protection Policy. You can unsubscribe at any time. For more information, please click here.  

More Hello! Fashion

See more