We Went Street Style–Spotting in London—These 7 Outfits Impressed Us

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We're back! After what feels like a very drawn-out winter, we've kicked our warm-weather street style series back into gear, and 2023 is already off to a stellar start on the outfit front. With the buzzing streets of London on our literal doorstep, we set out to find out what the capital's most stylish dressers are wearing this May, and we have thoughts—good ones. 

Our shoot was called off on account of rain, and when we did eventually venture out on a bright and airy Saturday, we didn't know what to expect. The skies may have been blue (at the start of the day at least), but there was still a discernible chill in the air. Ah, London—what are you like? Undeterred, we headed to the city's heart in the hopes of capturing the current mood of the streets and how people just like you are dressing this season.

After hours upon hours of scouting out the looks that grabbed us, some clear trends began to emerge. Firstly, heels are all but obsolete in London. Of course, I'm exaggerating, but it was surprising to see how few heels there were pounding the pavement, confirming that flats are where it's at right now. 

As it's nearly the start of summer, you might assume that the city's fashionable dwellers would be sporting their finest dresses. While we spotted a handful of classic white dresses on our travels, we observed significantly more trouser and skirt looks than ever before. Although full skirts and loose-fit trousers are trending on Instagram, there's no doubt this is transcending into real-life outfits too. 

Shall we see the street style looks that grabbed us in London this May? Simply scroll on. 

1. BALLET FLATS

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: Flat shoes have always been essential for navigating London, and right now, there are so many trending styles to consider. The most prevalent is ballet flats, which development manager Nicoletta makes a case for with her tonal ensemble. Her flats may be Chanel, but there are plenty of options on the market to suit every price point. For a fashion-forward take, style them with wide-leg trousers just like Nicoletta's H&M pair. 

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2. VIVID GREEN

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: In terms of the street style colour palette, neutrals are reigning supreme, but that doesn't mean bright hues are on the black. In fact, if anything, Vittoria makes a case for standing out with her green Zara blazer which matches her Bottega Veneta Jodie bag perfectly, something we're sure is no accident. 

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3. FULL SKIRTS

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: Make no mistake. This is the year of the skirt, with many versions—denim, plissé pleat, maxi and so much more—breaking through as major trends in their own right. Our favourite, however, is the full midi, which looks especially cool worn casually day-to-day. Although, it looks great dressed up for evenings out too. Make womenswear designer Ainslie your muse and style yours with a denim jacket and serious boots. 

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4. CARGO TROUSERS

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: If there's one thing we're certain of after our street style stint, it's that cargo trousers are still high on the style agenda in London. Although you can't beat a classic khaki pair in cotton, we are seeing fashion types gravitate towards fluid, softer silhouettes. Take inspiration from Bryonie, whose loose-fit Pangaia trousers further elevate her vintage jacket and velvet Zara shoes. 

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5. MARY JANES

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: While heels might not be quite as prevalent as they once were in the London wardrobe, some styles still prevail—so long as they're genuinely wearable for long periods. Cue kitten heels and Mary Janes, the latter of which we clocked immediately on marketing executive Lisa, whose Vagabond Mary Janes work perfectly with her pleated-skirt-and-cardigan ensemble. The socks? They complete the trendy, preppy aesthetic. 

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6. LITTLE WHITE DRESSES

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: White dresses are a staple in the wardrobes of many of us. (We know they're the first thing we reach for when temperatures allow.) Brit demonstrates the ideal way to wear yours when the weather isn't playing ball, styling her light Urban Outfitters midi with chunky black H&M boots. 

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7. BOMBER JACKETS

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(Image credit: MADDI KNIGHT FOR WHO WHAT WEAR UK)

Style Notes: It's the jacket trend that's dominating at Zara and Mango, but it's just as easily found on the second-hand shopping circuit too. We're talking about bomber jackets, the cover-up of choice of countless city dwellers if our day spent shooting is anything to go by. Nursery teacher Catherine's brown iteration feels especially current (rich chocolate brown was all the rage on the runway), and we enjoy the colour contrast between it and her creamy Cotton On jeans. 

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Next Up: 5 Throw-On Shoes Londoners Are Exclusively Wearing With Skirts

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over twelve years of experience in fashion journalism. She been creating engaging and elevated style content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories, and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, works closely with influencer talent on content initiatives, represents the brand at industry events, and regularly contributes to social media. Previously, Maxine appeared on TV in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o. 


Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship, she was offered a position on the Look magazine fashion desk. She accepted, leaving university a year early in the process. She went on to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion writer along the way. She later served as Look’s acting Editor in Chief before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others. Maxine works remotely from her countryside home near Edinburgh.