The subject of today’s textual conversation, Oliver Cheshire, is proving his smart, savvy, street style to be a big hit with not only the young men but women alike and has given him a social media following of over 100k; resulting in international designers clambering over each other to dress him in their latest collections.
Having started his career in the fashion industry aged just 17 when he was scouted by Select Models. Cheshire’s first campaign was with, a small little brand you may have heard of called, Calvin Klein fronting their iconic advertising. Since then he has gone on to the face of some of the biggest names in the fashion world, including Dolce and Gabbana, Versace, Missoni, Vivienne Westwood and Marks & Spencer.
His versatility and appeal have led him to work with some of the world’s most coveted and renowned photographers, including Mario Testino, Mert and Marcus, Bruce Weber and Steven Klein. Proving he’s not JUST a pretty face, Oliver’s style and in depth knowledge of men’s fashion made him the natural choice to become contributor for the Telegraph Men back in 2013.
This season his status continues to grow from strength to strength; confirming his place among the elite of the front row at London Fashion Week and London Collections Men.
Oliver is regularly heralded in GQ.com’s Best-Dressed poll from the US to the UK, aswell as winning places in similar features in publications such as Grazia, The Daily Telegraph and Tatler. He has also been labelled in the press as the “Model with the Midas Touch”; as brands like Orlebar Brown, Superdry and M&S have seen a direct increase in sales when Chiselled cheekbones has been featured as “Their Face”.
I think my biggest regret would definitely be not eating that piece of chocolate cake! Never turn down cake!
What’s your favourite piece of clothing?
Right now, I think it has to be my M&S pebble dash Derby shoes. They’re so easy to wear and go with everything.
Who is your style icon? Why?
I grew up as a 90’s kid seeing David Beckham everywhere. He took risks with his fashion, and set trends at the same time. He wasn’t scared to try new things. Now he’s a man who knows what looks great and sticks to it.
What piece of style advice do you live by?
Make sure you’re always properly dressed for the occasion and always follow the dress code on the invite.
Can you tie a bow tie? If yes, who taught you?
Embarrassingly, no! I had to look it up on YouTube.
Have you ever bought a piece of clothing and regretted it?
I’m usually quite good and really think about what I want before I buy it. I guess there are trends I wish I hadn’t tried; I’ve worn some pretty OTT printed shirts over the years.
What do you have to do after this conversation?
I’m going to a lovely dinner at the Rosewood hotel, their food is the best.
What would you like to be doing after this conversation?
Having a beer at the Rosewood with dinner and then eating lots of Percy Pigs!
‘Town Called Malice’ by The Jam, definitely my favourite song of all time.
How did you get into the industry, what was your big break?
I was scouted by Select Model Management at 16, they sent my Polaroid’s over to New York and I ended up being booked by Calvin Klein. I was really lucky and my career really took off from there, and I ended up walking (on a catwalk) for some really huge names.
If you could live anywhere where would it be & Why?
Probably New York. The atmosphere is just so cool out there and always buzzing. I have loads of friends out there too so I know I wouldn’t ever get lonely. Other than that I think I’d choose London.
It’s between the W in Barcelona (above) or the Maritime in Manhattan, they are two of the most amazing hotels I’ve ever stayed in.
What music are you listening to at the moment?
Stormzy, he won two MOBO awards, I would seriously suggest checking him out.
Best present you’ve ever received?
Pixie (Lott) took me on holiday to Florence once for a Christmas present; that was pretty awesome.
Best piece of advice you’ve ever been given and by whom?
Nothing is ever as bad as it seems.
Oliver Cheshire is the Face of Autograph at Marks & Spencer