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Dresses with boots: the best outfit formulas

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

Outfit consisting of grey cable knit, champagne slip, gold huggies and off-white wedge boots
Orin Carlin
Content Writer
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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, every single time.

 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?

MORE: Best designer black boots if you're looking to invest

 Valentina Ferragni wearing bomber jacker, puffy white mini dress and lace-up boots © Getty
Milan Fashion Week AW23

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.

READ: Jackets to wear with dresses: the failsafe outfit combos

RELATED: Best winter dresses for a hit of cosy chic

Hello! Fashion shares our favourite dress and boots outfit combinations: 

Chunky jumper dress + Biker boots

Outfit consisting of cream knit midi dress, biker boots and cream shoulder bag
Featuring Golden Goose's Embroidered Knitted Wool Maxi Dress

A straight-fit midi with chunky knit detailing is a cold month must-have, and the detail on this piece from Golden Goose's Journey collection feels a little different to your average cable knit. The relaxed shape looks great alongside the edgy appeal of a biker boot, and Celine's pair, complete with elegant gold hardware, has a certain timeless appeal. I'd complete the look with a slightly off-beat accessory - JW Pei excels in this area, and its Janna bag feels sculptural and cool.

Golden Goose Embroidered Knitted Wool Maxi Dress, £790.00, Net-A-Porter; Biker Mid Boot, £1,400.00, Celine; Jana Bag, £100.00, JW Pei

Printed mini + Knee-high boots 

Outfit consisting of print mini dress, monogram bag and croc-effect knee-high boots
Featuring Zara's Animal Print Tulle Dress

I love the drama of a mini alongside the sleek, sultry energy of a knee-high boot. Zara's abstract animal print version features flattering ruching down the sides and I think it would pair really well with a textured boot. Reformation's croc-effect Nylah design feels high drama, but with a functional block heel - great for a big night out. 

Animal Print Tulle Dress, £29.99, Zara; Nylah Nappa Knee Boot, £448.00, Reformation; Jacquard Shoulder Bag, £35.99, Mango 

Flowy ribbed midi + Cowboy boots

Outfit consisting of blue ribbed midi dress, silver cowboy boots and silver flap shoulder bag
Featuring H&M's Rib-Knit Dress

Knitted midis are worth their weight in style gold when you want to look put together sans the effort. I love this version by H&M in a pretty petrol blue - the boat neckline is practically guaranteed to flatter and the viscose-polyamide blend looks perfect for the ever-tricky transitional dressing period. I also love the gentle fluting along the hem for a hint of movement. Add a splash of Western drama via these silver cowboy boots from the Annie's Ibiza x Terry de Havilland collab and complement with Coach's molten metal Tabby 20 bag.

Rib-Knit Dress, £49.99, H&M; The Silver Cowboy Boot, £350.00, Annie's Ibiza x Terry de Havilland; Coach Tabby 20 Shoulder Bag, £395.00, House of Fraser 

Satin dress + Wedge boots

Outfit consisting of satin dress, grey cable knit, gold earrings and cream boots
Featuring Zara's Satin Dress

The silky lustre of a slip is hard to resist, and by layering Zara's champagne-coloured version under H&M's chunky grey cable knit, it feels pared down enough for everyday. Layering two relaxed-fit pieces results in an easy-breezy effortlessness, and I love the idea of the champagne hue alongside these faux leather H&M boots - they look far more expensive than they actually are. Top it off with a hint of metal via Mejuri's lobe-hugging earrings in 18k gold vermeil.

Cable-Knit Dress, £32.99, H&M; Satin Dress, £35.99 £9.99, Zara; Wedge-Heeled Boots, £64.99, H&M; Dôme Huggies, £58.00, Mejuri

Romantic knit + Sleek ankle boots

Outfit consisting of brown knit, croc-effect boots, khaki tote
Featuring Dôen's Estella Dress

Dôen's dreamy Estella dress has caught my eye, and I'm head over heels for the pretty ruffle detailing around the neckline, sleeves and hem. I love the earthiness of the chocolate brown hue, and think it would pair harmoniously with these sharp croc-effect ankle boots by Everlane. The curvature of the heel looks extremely luxe, and to close the ensemble I'd turn to Demellier's classic The New York tote for a chic office moment.

Estella Ruffled Pointelle-Knit Alpaca-Blend Midi Dress, £447.96, Net-A-Porter; The Banana Heel Boot, £261.00, Everlane; The New York, £480.00, Demellier

Why you should trust me: 

Orin Carlin is Hello! Fashion’s SEO Content Writer. Promising to leave no stone unturned in the name of fashion and beauty journalism, she is the proud creator of our ‘Try The Trend’ series. With a particular interest in formula innovation, microtrends, royal and bridal beauty, perfume, rituals, treatments, fashion history and vintage icons, she can either be found interviewing major industry names (previous subjects include Georgia May JaggerMary Greenwell and Sam McKnight) or scouring the internet for must-have pieces. It's not just a job; it's a personal quest to unearth noteworthy pieces that resonate with style and beauty enthusiasts.

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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.

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