I Tried On 50 High-Street Dresses to Work Out Which Ones Go With Boots

Here at Who What Wear UK, we're all about delivering the latest and greatest shopping edits, as approved by our team. That's why we've created a new shopping column, The Joy of Shopping, which will see me, Joy Montgomery, heading to all your favourite stores to test out new-in pieces IRL. From summer dresses to the brands you might've forgotten about, prepare for changing room selfies aplenty. Is there something you'd like me to cover? Make sure to tweet or Instagram me your requests!

One of my favourite moments in The Devil Wears Prada is when Andy Sachs sashays into the office clad in a pair of leather thigh-high boots. "Are those the…?" asks Emily, open-mouthed. "The Chanel boots? Yeah they are," replies Andy with a serene smile. Much like Julia Roberts's Pretty Woman power suit or Sandy from Grease's biker-jacket-and-perm makeover, these boots become a marker of Andy's new don't-mess-with-me persona—a gateway into a strange new world. Yup, fashion can change lives, kids. 

I might not be rocking Andy's designer stilettos, but I can certainly testify to the outfit-transforming powers of a good boot. Three years ago I purchased a pair of black knee-highs from Zara, and last year was kindly gifted some chunky lace-ups from ASH. They have both been loyal companions over many a cold winter morning and, sartorially speaking, there's not much they can't do. 

From my experience, you can cover most bases with this boot power duo. My knee-highs are perfect for adding a grown-up polish to any outfit, while lace-up boots have a more toughened, cool-girl edge. This season in particular there seems to be a surfeit of winter-ready frocks that are begging for a good boot pairing, from floaty midis and jumper dresses, to thigh-grazing smocks and tweed minis. I'm also using my boots (and good 'ol roll-neck) to adapt my favourite summer dresses for the colder months. 

Not sure where to start? Let me be your guide. Jumper dresses have made a serious comeback this season and exude minimalist chic when worn oversized with knee highs—Arket is great for quality pieces. There's also a resurgence of minis, which will look just as good with heels, for a little '60s styling, as they will with flats (very Alexa Chung). There are also plenty of classic long-sleeved midis and work-ready shirt dresses to go around. Scroll down to see and shop my full edit.

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Joy Montgomery

Style Notes: I never thought I'd see the return of the humble jumper dress, but here we are. This Arket number looks so chic with my knee-high boots and is nothing like the itchy iterations of the noughties. It would also look fab over wide-leg tailored trousers. 

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Joy Montgomery

Style Notes: The utility undertones of this H&M midi were made to be worn with my chunky ASH boots. I've seen a lot of orange around at the moment, and I was surprised by how wearable it was, plus it complements more neutral autumnal shades such as beige and cream.

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Joy Montgomery

Style Notes: When Who What Wear's Social Media Editor Alyss tried the floral version of this dress on, I was totally sold. The polka-dot print offers a more classic alternative and will look just as good with heels or sneakers as it will with knee-high boots. 

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Joy Montgomery

Style Notes: Hot pink is a colour I wouldn't usually try, but Arket knows how to give it a cool, minimalist twist. The sculptural silhouette of this knee-length dress is its selling point, and I can imagine it would look cool over a roll-neck base-layer.

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Joy Montgomery

Style Notes: I'm a sucker for this season's smock dress trend, especially when it's paired with winter-ready black. While some like to embrace the pretty proportions with ballet flats, I prefer to balance things out with my utilitarian lace-up boots. 

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Joy Montgomery

Style Notes: Alongside its more avant garde offerings, & Other Stories always stocks a generous selection of flattering, work-ready styles. I seriously rate the flattering waist-tie detailing of this polka-dot midi, and it's also the ideal length for knee-high boots.

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Joy Montgomery

Style Notes: & Other Stories has really pushed the boat out with this shirred number, which comes with a body-skimming style, statement cuffs and a hemline that falls to the ankles. Due to the long length, I would recommend opting for a heeled pair of boots. 

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Joy Montgomery

Style Notes: When it comes to dresses that go with boots, you can't really go wrong with a printed midi, such as this H&M buy. The statement shoulders and graphic print make it stand out from the crowd, but it would also look great layered under a roll-neck jumper. Shop a similar style below.

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Joy Montgomery

Style Notes: I've been eyeing this puff-sleeved number for a while, and to be honest, in real life it's more princessy than I expected, so I experimented with styling it with my chunky boots and the effect was surprisingly cool. I can also imagine it being a winner for a winter wedding.

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Joy Montgomery

Style Notes: I can't quite work out if this is a party dress or a daytime number, but perhaps therein lies its appeal. The plunging neckline says party, but the loose fit and long sleeves say weekend, so why not wear for both? Match the heel height of your boot accordingly. 

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Joy Montgomery

Style Notes: Minis are making a comeback, and I'm totally okay with it. My favourite way to wear the trend is to embrace the '60s aesthetic with a high neckline, funky print and knee-high boots. FYI Topshop has a great selection of minis right now.

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Joy Montgomery

Style Notes: When it comes to jumper dresses, I tend to prefer looser silhouettes, however, the square neckline of this ribbed maxi caught my eye. It's probably a little on the tight side for my taste, but it would look fab on bigger busts. 

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Joy Montgomery

Style Notes: Topshop Boutique is the place to go for fashionable twists on smart-casual staples. Case in point: this silken green midi comes in a premium-feel fabric and chic and simple silhouette. Adapt for your Christmas party with strappy heels and statement earrings.

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Joy Montgomery

Style Notes: This is another dress that would be useful for those working in more corporate environments. The fit is timeless, flattering and winter-appropriate, but the print gives the get-up a throwback, '70s-inspired edge.  

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Joy Montgomery

Style Notes: If you're a fan of knitwear, then you need to get down to H&M because its Pringle collaboration is seriously good. This long-line jumper dress is so cosy and warm but definitely on the baggy side, so maybe avoid if you're not into the oversized look.

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Joy Montgomery

Style Notes: Arket's famed shirt dress is back for another season, and this time it comes in a vibrant floral print. The cut is slightly looser than past iterations, which is good news for those who loved the Zara polka-dot dress. This would look fab with both flat and heeled boots.  

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Joy Montgomery

Style Notes: This week I unearthed an old tweed mini dress and styled it with knee-high boots and was pretty happy with the overall look. This Mango number creates the same effect when layered over my grey roll-neck and with my black boots—a very retro approach to winter layering.