I Tried on 50 High-Street Dresses to Work Out Which Ones Go With Tights

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 Team WWW UK has created this offshoot shopping column as part of our We Try Before You Buy franchise, in which I, Joy Montgomery, will be heading to all your favourite stores to test out new-in pieces IRL. From summer dresses to intriguing brands, prepare for changing room selfies aplenty. Is there something you'd like me to cover? Make sure to tweet or message me via Instagram for requests.

We Brits are no strangers to tights. From the laddered woollen pairs we wore on the playground to the sheer pairs we wore for nights out in university, tights have been our constant companions during long, bitterly cold winters. I've never understood the tights snobbery that exists about them in the fashion world. There seems to be a "survival of the fittest" mentality as to who can stay bare-legged the longest. What I love about tights is that you can use them to extend the shelf life of your summer dresses, which can only be a good thing for our bank balances. (As a child, I insisted on wearing my summer frocks even in the depths of winter, so you can't say I don't practice what I preach.)

While I could spend hours waxing lyrical about the joys of tights, I understand they're not always the easiest thing to style. Annoyingly, there's no exact formula, but I generally find that most longer dress styles look good with thicker tights (luckily midis are everywhere at the moment). When it comes to wearing hosiery with shorter dresses, it's best to stick to black boots to create a seamless line—although I do think some of this season's vintage-inspired minidresses would look great with snakeskin boots. Need a bit of inspo to help you on your way? I went to some of my favourite high-street stores to try on the dresses that look stylish with tights. Scroll down to see and shop my edit.

Best winter high-street dresses: Joy Montgomery wearing & Other Stories floral dress

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Joy Montgomery

Style Notes: The bold print, statement ruffles and asymmetric cut of this & Other Stories midi dress instantly caught my eye. I was happy with the proportions, however, I found that the fit was slightly more snug than expected (particularly around the hips), so I would consider buying a size up.

Best winter high-street dresses: Joy Montgomery wearing Warehouse leather dress

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Joy Montgomery

Style Notes: Leather dresses are on their way to becoming this season's look du jour, and this faux-leather iteration from Warehouse gets my vote thanks to its Western-inspired details.

Best winter high-street dresses: Joy Montgomery wearing & Other Stories orange dress

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Joy Montgomery

Style Notes: This sheer stripe midi dress is perfect for the colour ambivalent (aka me), as it feels like a more approachable, autumnal shade of orange. I also love the billowing sleeves, which offer a high-end finish to the whole look.

Best winter high-street dresses: Joy Montgomery wearing Topshop polka-dot dress

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Joy Montgomery

Style Notes: This polka-dot mini is an '80s-inspired dream. While it would be perfect as a party piece worn with heels, I enjoyed layering it over a skinny roll-neck for a more laid-back aesthetic.

Best winter high street dresses: Joy Montgomery wearing Warehouse stripe dress

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Joy Montgomery

Style Notes: I wasn't sure about this dress when I saw it on Warehouse's website, but it's far better-looking IRL. The fabric hung really nicely and didn't feel cheap like some silky high-street pieces do. If I could change one thing, I'd make the sleeves full length.

Best winter high-street dresses: Joy Montgomery wearing Warehouse zebra-print knit dress

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Joy Montgomery

Style Notes: I wouldn't usually go for a maxi knitted dress, however, I can't resist a zebra print (plus, it'll be super warm in winter). This is a rather tight fit, but I like how the dress flares out at the bottom to balance out the top half.

Best winter high street dresses: Joy Montgomery wearing H&M red ruffled dress

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Joy Montgomery

Style Notes: This H&M look is so Little House on the Prairie, and I'm not even sorry. It was born to be worn with lace-up boots, woollen tights and a heritage coat.

Best winter high-street dresses: Joy Montgomery wearing Arket silk midi dress

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Joy Montgomery

Style Notes: This silk midi is the sort of piece Arket has been doing so well since its inception. If you've got an Arket dress lingering from the summer, you'll be happy to hear that they work just as well with tights for the colder months. Steamer required.

Best winter high street dresses: Joy Montgomery wearing Topshop green midi dress

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Joy Montgomery

Style Notes: Topshop just keeps knocking it out of the park with these expensive-looking ruched party dresses. I'm obsessed with the green-and-black print of this long-sleeved midi, which I've paired with a roll-neck for extra warmth. 

Best winter high-street dresses: Joy Montgomery wearing & Other Stories cord mini dress

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Joy Montgomery

Style Notes: This & Other Stories cord dress was one of the few shorter styles I tried on and loved. I purposefully picked it because it works well with a long sleeved top layered underneath (this sheer polka-dot top does the job nicely). Also, this is the sort of dress that actually looks better with tights. So Alexa Chung.

Best winter high-street dresses: Joy Montgomery wearing H&M floral midi dress

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Joy Montgomery

Style Notes: I tried on this dress because it reminded me of a designer piece I loved last season, except this H&M one comes in at a tenth of the price. I particularly like the Western-inspired, yolked collar detail (can you tell that I like this trend?)

Best winter high-street dresses: Joy Montgomery wearing & Other Stories pleated midi dress

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Joy Montgomery

Style Notes: Cutting off just below the knee, this & Other Stories checked dress is a good option if you're worried about longer styles swamping you. The pleated and ruffled neckline skirt is so pretty. Plus, the check is very A/W 18.

Best winter high street dresses: Joy Montgomery wearing Arket knitted midi dress

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Joy Montgomery

Style Notes: The perfect respite from the bold prints and vibrant colourways. Only Arket could create a knitted dress this chic. I'm a big fan of the fitted neckline and was impressed at how the brand managed to create shape with the woollen fabric.

Best winter high-street dresses: Joy Montgomery wearing H&M pussy-bow mini dress

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Joy Montgomery

Style Notes: This drop-waist dress from H&M might not be for everyone, but I like its vintage vibes and think it offers a good mix of distinctive detailing.

Best winter high-street dresses: Joy Montgomery wearing Arket zebra-print dress

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Joy Montgomery

Style Notes: I've had my eye on this zebra-print silk dress for months now, and it's the perfect example of how a dress can be adapted for all seasons. 

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