The 27 Street Style Outfits That Have Inspired My Style

September 27, 2020 at 06:00AM

The street style phenomenon might’ve only kicked into gear in the last decade, but in that time, it has had a fundamental impact on the way that fashion has evolved and adapted to an ever-shifting consumer landscape. No longer focused on the hallowed halls of the runway, the camera has gradually turned its lens to the pavements outside of the venues, capturing the well-dressed attendees in all their finery. 

While it has been called a circus by some (and there’s no denying, at some points the peacocking did reach excessive levels), but ultimately it has been an exercise in democracy, allowing “the people”—albeit very shiny people—to have a say in the trends they actually want to wear. Yes, there are always cases of #spon outfits and not-so-candid group posing, but I have always loved scrolling through the latest intake of street style imagery every season, particularly from London Fashion Week. Eclectic, joyful and individual, London has quite rightly become known as the personality city in the fashion week lineup. 

Of course, this season, we haven’t had the usual lineup of looks due to the 2020 spectre that is COVID-19, so in its place, I went down a bit of a Getty hole (technical term) to find the outfits that have captured my imagination and inspired my style over the years. From Alexa’s minidresses to the dawn of the tonal outfit, scroll down to see my highlights. 

I’ve long been an Alexa fashion fan, and in my opinion, this 2017 look perfectly optimises her cool-girl-with-a-retro-edge aesthetic. 

When I spotted this ’70s-inspired Eudon Choi jacket in the London Fashion Week street style shots, I was instantly besotted. 

I’ll never say no to a bit of Western-inspired styling, and a fringed jacket is one my fave ways to elevate a pair of jeans.

Sometimes it’s the low-key looks that make the biggest impact. Case in point? This chunky knit-and–tailored-trousers combo is perfection. 

If you’re a coat lover, then London is your place for you. This high-shine trench is ideal for September’s transitional temperatures. 

Back in September 2016, Pandora Sykes championed the now hotly coveted fashion brand Rejina Pyo with a sunny yellow frock.


I don’t usually wear super-bright colours, but this street style shot totally converted me to the “neutrals with a pop of neon” cause. 

Pale yellow was all over the LFW pavements in February 2020, and it made for the perfect pairing with the season’s beige-toned neutrals. 

Londoners know how to layer, and this chic outfit shows the power of a well-chosen roll-neck. I now use this cold-weather styling hack every winter.

More often than not, the big fashion editors aren’t the ones in the look-at-me ensembles. They generally stick to immaculate tailoring and quietly chic accessories. Less is always more. 

I am always here for a good coat, and I enjoyed the statement-making powers of the oversize trench trend. I wear my & Other Stories iteration every autumn without fail. 

A boxy blazer, flares and a printed roll-neck? Yep this is my perfect outfit formula all year round.

This model snapshot might date back to September 2013, but the pared-back appeal of a chunky cardigan and jeans remains. Classic styling embodied. 

This showgoer braved the storms in this dreamy checked coat, and I’ve been thinking of it ever since. 

Another day, another fringed jacket. I love the proportions of the knee-high boots with the thigh-grazing oversize jacket. 

I’m not going to lie—I was (and still am) a total convert to the tonal beige outfit trend. It’s my one-stop shop for expensive-looking style.

Oh, Alexa, have you ever not looked good? Back in Feb 2017, Ms Chung made us all want to buy a shearling biker with this high-low look. Okay, I still want one now.

The frou-frou feather trim on this pair of trousers instantly adds interest to this showgoer’s neutral blazer and white tee. A dreamy cocktail party outfit if I ever saw one.

This is one of the most perfect leather coats I’ve ever seen. Going head-to-toe leather might not be the most practical option, but this outwear hero would look just as good with jeans.

Another example of the powers of a tonal outfit, but this time in 2019’s pale-yellow trend. So elegant yet seemingly so effortless.

I couldn’t not include a jumpsuit in my street style roundup, as I think I wear a one-piece at least once a week. I like how versatile they are. For example, this white iteration looks super polished with heels.  

I told you fashion editors love a bit of tailoring. Vogue’s Sarah Harris opts for a classic navy-blue suit layered over a camel-coloured roll-neck. The effect is beautiful yet so powerful. 

We lost count of the number of people we saw in this JW Anderson jumper last year. It remains a favourite of mine. 

I stumbled across this retro-inspired look in the London Fashion Week archive, specifically June 2015. I would happily recreate this outfit now (except without the baker boy hat).

From being a “Who can wear the most outrageous item of clothing?” parade, street style has become more subdued in recent seasons, and I’m not sad about it. I really enjoyed the pairing of a longline blazer and midi skirt in this classic ensemble. 

An oldie but a goodie. You know that someone has an amazing personal style when an outfit from four years ago looks just as good in the present day. I’m a big fan of the waistcoat layering situation here.

It was all about the headband for A/W 19, and I like the almost Tudor-esque vibes of this midi-dress–and-boots pairing. 

Up Next: Autumn/Winter 2020 Trends: The New Fashion Looks You Need to Know

Author Joy Montgomery | Whowhatwear
Selected by CWC

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