The most stylish footballers in the world, as told by Twitter’s most popular fashion expert
The link between football and fashion culture has been long established. Since George Best donned his eclectic, unique style in the 1960s, footballers have always found ways to stand out and try to be more stylish than the next guy. In recent years, this trend has skyrocketed.
Famous footballers are now brand ambassadors for luxury fashion houses. Jack Grealish is signed to Gucci and Jude Bellingham is a Louis Vuitton ambassador. Barcelona have turned their player stadium entrances into biweekly catwalks, with Jules Koundé, Raphinha and Sergi Roberto often competing to see who can pull off the most egregious (*stylish), outfits.
This article will analyse which footballers have really got what it takes to walk at Paris Fashion Week, and which should stick to their club tracksuit. Unfortunately, I don’t have the critical analysis necessary, but I’ve recruited someone who does!
Derek Guy is the most popular menswear expert on X (formerly Twitter). He has gained fame on the app as ‘the menswear guy’, giving fashion tips to, well, anyone who has the app. Since Twitter pushed out the ‘For You’ feature, Derek has become synonymous with men’s fashion and styling tips and his easy-to-read, intriguing content and hilarious tweets find themselves on many men’s feeds.
me tweeting about actors with multi-million dollar careers: “jacket too short. trousers too tight. wrinkles.” pic.twitter.com/q4PNNOFj3V
— derek guy (@dieworkwear) March 11, 2024
Want to know what Keir Starmer and Rishi Sunak got right and wrong with their styles ahead of the election? He’s your man. Do you want to see an extensive amount of sophisticated photos of Ralph Lauren? He’s also your man. Styling critiques of Donald Trump’s suits which shift his shoulders to make him look like a linebacker? You guessed it, he’s also your man.
Now, Derek claims to know close to zero about football. What he does know about is style. When we discuss the following player’s outfits, he has heard of Cristiano Ronaldo and Lionel Messi, but even the term Mohamed Salah was alien to him. So now you know his critiques are purely objective and style-based.
Which players are the most stylish?
Jackson Irvine
Jackson Irvine isn’t particularly well-known for his footballing prowess (sorry, mate), but he is making waves for his off-the-pitch fashion sense, humour and down-to-earth demeanour. He went viral for a clip in which he was visibly touched by Manchester United and Brazil midfielder Casemiro recognising him at the FIFPRO World 11 awards ceremony.
His style often encompasses his profession, mixing football shirts with streetwear items.
“I like it… but tucking in a jersey just seems a little tidy, a little too mannered”, Derek says as he peruses over the slides of Irvine rocking different retro shirts.
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His best outfit is the one in which he’s wearing a green jacket. An outfit works best with layering as jackets tend to have more interesting silhouettes. The jacket lends something to the outfit, and the necklance and the beanie add extra style.
– Derek
I frantically write down this style gospel, reevaluating everything I thought I knew prior about style (not much, to be fair) and he offers some final remarks.
“He looks good…”
Derek Guy – ‘The Menswear Guy’ (henceforth just Derek)
i dont know who needs to hear this, but your identity is not your job. your identity is a sick ass jacket everyone recognizes you by
— derek guy (@dieworkwear) November 15, 2023
Cristiano Ronaldo
Ok, now we’re moving on to one of the heavy hitters. Even Derek has heard of Cristiano Ronaldo. CR7 isn’t necessarily known for fashion, but the amount of awards ceremonies that he’s rocked up to means that there is ample material to pore over.
“I like the use of the turtleneck, although the jacket is cut a bit short”, Derek says of the first suit. “I’m not crazy about the elasticated waistband”.
His eye for detail is quite incredible, I hadn’t even noticed the elasticated waistband. I think that might say more about my lack of an eye for detail in the fashion world though…
“The trousers are a bit low-raised and one should never wear a belt with a dinner jacket. Instead, CR7 should add a cummerbund which would cover the flash below the jacket’s covering point” he says of the second suit.
It’s the worst of the three. A suit jacket with jeans is a NO!
Derek on the third suit
A tailored jacket should not be accompanied by jeans, or for that matter any trouser that isn’t the pair that the jacket came with. As well as that, the tie and pocket square should not be made from the same material.
“The top is very formal, and the bottom is very informal. The top is like a fireman, and the bottom is like a motorcyclist, it just doesn’t go”.
The third suit
i’ve noticed that people don’t wear waist coverings anymore at black tie events (pics 1, 2). this looks very bad, esp if your shirt peeks out from beneath your coat’s buttoning point. you need a cummerbund or formal waistcoat (pic 3, 4). looks much more elegant. pic.twitter.com/628UFHAzwJ
— derek guy (@dieworkwear) July 6, 2024
Jadon Sancho
Sancho is one of the most talked about figures in the football x fashion game. His breezy, streetwear look is a big hit amongst fans, especially young ones. If there is a figure to apply modern terms such as ‘drip’ and ‘aura’ to, it would be Sancho.
I like the looks!
– Derek
“The average person can’t pull off the hats, but he can pull it off”.
I explain that the streetwear style is a big part of Sancho’s vibe. He grew up in Kennington, an inner-city borough of London where fashion is a way of identifying oneself and standing out. He’s a regular attendee at Fashion Weeks or launch parties of designer brands, and this is how Sancho expresses himself.
“The pre-distressed jeans seem a little burnt out at this point. They were, if ever, much more 2014, 2015 than today”. I think this is one thing that I could’ve definitely identified myself, so I was pleased to hear this.
“What do you think of the massive chains?”, I ask.
“I’m a huge fan of diamond Cuban links, and it suits his personality”.
Memphis Depay
Depay is one of the most versatile dressers in the game, and he has all sorts of looks. I show Derek five different outfits, representing five different styles that he has. A footballer who also has a rap career on the side and was engaged to Lori Harvey is always going to have a distinct, stylish look, and Memphis certainly does.
I really hate the faux patina they put on leather jackets. I also generally don’t like any outfit where there’s a tie, but no tailored jacket
– Derek on the final fit
I express my admiration for the first two outfits, the suited ones, and Derek agrees that the tailoring is really nice and he looks sharp.
The other outfits look great!
– Derek
Leo Messi
Like Ronaldo, Messi is not known for his fashion but for his footballing prowess. He might be one of the only men on the planet who look much more at ease playing against Chelsea rather than wearing Chelsea boots. Far better at making Jerome Boateng look silly than looking silly dressed in Ozwald Boateng. You get the gist.
When Messi picked up his EIGHTH Ballon d’Or award, the stars packed into the audience weren’t even the ones that shone the brightest at the Théâtre du Châtelet as the GOAT rocked up wearing a sparkling suit.
Derek agrees, noticing the high quality of tailoring in the suit due to the way it sits on his shoulders.
For the other outfits, he’s not as complimentary.
He’s a guy with broad shoulders and an athletic build, but in the Thom Browne suit, he looks unflattering. He looks pear-shaped.
– Derek on the middle picture (Messi in a Thom Browne suit)
Derek is particularly scathing of this final photo. “It’s the worst. A formal top with a tailored vest combined with predistressed jeans with ankle exposure. There’s no coherence, no message. Messi should get rid of everything and ask himself what he wants to communicate at that event”.
Tom Davies
The Sheffield United midfielder, formerly on Everton, is probably the only man who dresses as he does in the city of Sheffield. Davies has a distinct look, testing the concepts of menswear and experimenting with more typically feminine garments.
Derek laughs as he sees the contrast of Tom Davies on the Citi bike. A man with a jacket worth thousands of dollars sitting on the bike which costs $4.79 to unlock for 30 minutes. The bike has probably never seen such opulence.
The look on the left has Derek confused. Really confused. He studies it for a while before concluding why it doesn’t make sense. For him, the pieces individually are all nice enough, but as an outfit it doesn’t make any sense.
What has happened is that the jacket material is too thin and the shirt below is too thick. As layers progress outwards, it’s easier to do so as the layers get heavier. He looks more at home in the following photo.
– Derek
In that final photo, the cut of the clothes has much better proportions, a much better “rule of thirds”. It has a good silhouette.
King Felipe consistently looks great, and it seems that all of his suits are cut by the same tailor.
— derek guy (@dieworkwear) July 17, 2023
Some basic points:
1. Collar always hugs the neck
2. No pulling anywhere. Things hang cleanly
3. Lapels end about halfway from collar to shoulder bone (nice proportion) pic.twitter.com/JJcgHLrdHf
David Beckham
For me, the GOAT. You don’t get more classy than David Beckham. He’s done all of the looks and is stylish in all of them. In the late 90s, his outfits drew attention weekly in the back pages of the British media. Posh x Becks became the country’s second most famous couple, after the Queen and the King. Everything he wore, said and did was in the papers. So, everything he wore, said and did was done with style.
He looks great in the photo with the tanned suit. It’s coordinated and the pocket square and tie aren’t matching.
– Derek
He’s also a fan of the skipper collar polo and the nice green jacket that Becks sports in the last photo. A big fan of his more recent looks, he’s more sceptical of the classic Beckham looks.
Wearing the durag is just a bit cheesy. Removing it on the bottom (the photo next to Victoria with the drink in his hand) would look good.
– Derek
The leather jacket combined with, well, more leather is very daring. It may be best to slightly unzip the jacket, he mentions. He’s neither crazy about what he calls the Justin Timberlake look (see photo with dirty-looking jeans and purple shirt) nor the second Wimbledon photo of the selection. Beckham sports bellow pockets, which are typically used to hold bullets for hunting. A strange choice for Wimbledon, I must say.
He’s clearly a guy who cares a lot about clothes… but he looks good
– Derek
A slightly fuller silhouette introduces another important quality: romance. There’s very little romance in David Beckham’s slim topcoat. But Delon’s topcoat has broader shoulders, a voluminous chest, and wide lapels. The coat shifts and flows with him. Very romantic. pic.twitter.com/peags1rrZi
— derek guy (@dieworkwear) August 18, 2024
Son Heung-Min
Clean on and off the football pitch, Son is one of the most loved figures in the sport. What’s more, he looks good. His outfits are clean, well-fitting and stylish.
All of these look good to me. The brown tweed combined with the tennis sweater is excellent. He looks really stylish.
– Derek
Apart from suggesting what Sonny might look like with a chunky sweater and an unbuttoned jacket in the middle photo, Derek was very impressed with the Stylish Son.
Mohamed Salah
Salah has torn up the Premier League since he arrived in 2017, and his latest sidequest is to tear up the fashion game too. Salah brings Egyptian style to England, with his quintessential curly locks adding to every look.
He looks great in the tuxedo. I love the waist covering.
– Derek
The Adidas x Gucci jacket looks very slim, but he still looks good. It has a rather unusually wide lapel for a slim jacket.
Some infamous footballers style pictures…
DB x VB: It’s a pretty good cut for a suit although the sleeve is quite narrow. Derek then laughs, pauses and delivers what may have been the most cutthroat but apt evaluation of our nearly one-hour chat.
It’s just so fucking purple. They look like candy in Willy Wonka’s factory.
– Derek
Brutal? Yes. Hilarious? Definitely.
The United Boys:
The outfits in this photo look a lot better than the other two. It matches their personalities and surroundings. Is it going to be on the cover of Vogue? Probably not. But it looks a whole lot better than the other guy (Neymar).
– Derek
Neymar:
It makes no cultural sense. Suede boots, a fedora, shining dinner jacket, baggy shorts. It looks like someone threw clothes on him with a pitchfork.
– Derek
Lol.
The Most Stylish Footballer Rankings – according to Derek Guy:
1. Son Heung-Min
Winning on and off the pitch.
2. Memphis Depay
He’s so versatile, this was expected.
3. Jadon Sancho
“His streetwear style feels authentic to him” – Derek.
I think at this point it’s sensible to leave a little gap. Derek paused for a while before smirking and announcing that “there’s a whole lot that he didn’t like”. I suggest that the next choice could be framed as the fourth least bad as opposed to the fourth best. We continue.
4. David Beckham
DB7 will always be number one in my eyes but he has to settle for fourth on this list.
5. Mohamed Salah
Salah looks clean. Not the best, not nearly the worst.
6. Jackson Irvine
Irvine’s football outfits are cool enough, but a little mannered and unlayered for Derek’s taste.
7. Tom Davies
Respect for the bravery and ambition in the outfits, but not too sure of the exact direction in which Tom Davies is going in some of his outfits.
8. Cristiano Ronaldo
So it seems that Ronaldo didn’t get too many style points from Derek, but he can console himself with his five Ballon d’Or titles and countless trophies.
9. Lionel Messi
Look, it seems like the more focused on football one is, the worse their fashion is. Sort of. I just need a consoling statement to make Messi and Ronaldo feel better. I’m sure they’ll be ok.
A huge thank you to Derek for his input and for his generosity in the time he took to talk to 365Scores. Make sure to give Derek a follow on X as well. @Dieworkwear.
By Nicky Helfgott – NickyHelfgott1 on X (Twitter)
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