From humble beginnings to the incredibly flamboyant outfits he regularly sports on the pages of magazines, Harry Styles’ style is undeniable. It is in the name, after all.

Some have even gone so far as to consider him the fashion icon of our generation.

Although his musical talent is at the core of his fame, like a slew of other celebrities, his fashion choices play a huge part in his public persona. However, unlike most, his outfits and photoshoots are consistently polarising – often sparking public debate.

With the help of his stylist Harry Lambert, Styles’ wonderfully tailored and beautifully paired ensembles he is best known for exceed all expectations – good or bad. And although he’s definitely not the first popstar to shock audiences and bend gender binaries with his fashion choices – and he most definitely won’t be the last – the attention he garners from doing so feels progressive in the current climate.

In admiring his many, many outfits, I wanted to find out, is Harry an enigma of our time or could it be replicated by a mere mortal and still look cool?

And so, I recruited my younger brother, a gracious and helpful soul and a true style king in his own right to try and emulate some of Harry’s most iconic fits throughout the years.

Although I didn’t get him into any dresses, I was proud of his efforts and think he pulled the majority of the outfits off swimmingly.

Here’s to proving that if my brother can do it, so can you.

The Classic

I’m sure this one was the most painless look for my brother and something he would be regularly found sporting. An unfaultable combo, the classic white t-shirt and jeans look was a huge staple for Styles in his early days. Keeping to Style’s preferences, we rolled up the t-shirt sleeves for some cheeky upper arm action.

The Cardi

Unfortunately, I don’t own one of the iconic JW Anderson cardigans that were literally named after Harry, so I instead put my own twist on his often sported grandma-chic look. For this, we layered two cardigans on top of each other, chucked on some pearls and a chain, and paired with some high waisted pants with a chunky belt, bringing back just a touch of masculine appeal.

The Black Suit

This look is a bit of a mixture of a couple of his looks, mixing both feminine and masculine elements. The necktie detail is inspired by his Met Gala frills, while the sleek black suit with white details is taking inspo from his Dunkirk red carpet look.

The Grandpa Vibes

If you haven’t already heard, the sweater vest is in this season thanks to TikTok and Harry does it better than most. To best emulate Harry’s scruffy ‘just-finished-work’ grandpa look, we paired the vest with an oversized striped shirt making sure to roll up the sleeves in true Style’s fashion.

The All White

My personal favourite! We both agreed my brother BODIED this look. I had a vision for this look and was overjoyed with how it came out. It’s such a movie star 70s vibe and although our white suit may not have been as expensive and custom made as Harry’s, it works perfectly. The yellow aviators really top it all off and add a bit of colour into the otherwise totally monochrome look.

The Gucci

Navy suit combo with a jacket over the top. Probably the most fashion forward of all the looks while being obviously so Harry. We had to safety pin the blazer for a more double breasted look but I think the safety pin brings a touch of edginess to the outfit. My brother totally loved this look and maybe he even pulls it off better than Harry himself. Who’s to say?

The Shirtless Jump

Although we didn’t have a mini trampoline on hand for this one, this one was the most fun to shoot. Putting my brother in some loosely fitted feminine pants definitely pushed him out of his comfort zone but he had lots of fun with it still. This outfit is on the unwearable end of the spectrum but I think he still pulled it off. Maybe just not a supermarket appropriate fit.

Lover of people and writer of words, Ruby produces content in an attempt to make some sense of the world. You’ll often find her obsessing over and writing about anything art, design, fashion, culture or internet related. You can find her on Instagram or Twitter.