My Style: Oliver Cheshire

Portrait of Oliver Cheshire

Portrait: Courtesy of Oliver Cheshire

Are there any style combinations that you object to?

The only thing I object to is dressing in one style—who wants to eat the same food every day? Why would you want to stick to a certain polo and trousers combination when you have unlimited options and can be anyone you want? People say I'm a chameleon when it comes to style, but the only thing I really do is dress for the music I listen to the day I wake up or by what catches my eye. I truly think that no one should have one style only.

Please describe your style in three words.

Sporty, daring, and smart.

What is the biggest mistake one can make when getting dressed?

Not asking about the dress code before they go somewhere. If you don't dress for the occasion you will look and feel out of place. Men are so bad at it whereas women always do that—and it’s a very simple and easy rule.

Do you believe in role models?

Yes, I take style cues from a lot of people around me. David Beckham was a role model for me when I was growing up. Straight males rarely take risks and push the boundaries of fashion, but David has always been an exception to this.

What are your favourite fabrics?

There are quite a few. Definitely leather, I am a big fan of leather jackets. I also think that linen is very underused and it can be extremely chic if done correctly. Every man should have a silk shirt moment in their life (or make one). Wool is rather underestimated and I am really excited about the fact that it will be used extensively in sportswear during the next few months—something that I find very intriguing.

Which city has the best-dressed men?

London obviously, Savile Row is second to none. Having said that, I do like the way Scandinavian men dress — they have a minimal way of dressing which is quite pleasing visually.

Would you say that you are conservative or bold?

I wouldn't say I'm a mad dresser; I stick to the rules but I do try to experiment and push boundaries whenever I can. I probably am a bold dresser to quite a few people out there, but they too could pull off more styles. They don't think they can, but they do.

What are the rules in the way you dress?

Shape and fit are very important to me. If what you are wearing doesn't fit right, it's not going to look nice regardless of your body type. Little changes can do wonders to your outfit if you really know how to pay attention to the details.

Celebrities and style...

Love them or hate them, you are going to be stuck with them for a while!

Name one garment/accessory that you can never have enough of?

White trainers, they literally go with everything. I feel the world has moved on and sportswear is a major influence in all spectrums of fashion, therefore the right trainers can pretty much be combined with everything.

A man should always look like…

A man.

Who taught you what you know about style?

All the editors, stylists and the very creative people I have worked with throughout the years. They definitely opened up my eyes to possibilities and ways of catching attention with my style—and when you are interested in style as much I am, you read, learn and absorb all that knowledge.

How do you select your clothing every morning?

I don't plan at all, I literally decide based on the mood I wake up in and the songs I have been listening to. If I'm having a bad hair or skin day I go for a hat and hoodie, if not I go for something bolder and fun.

What is your biggest regret?

There are quite a few photos that I look at and go “Jesus, what was I thinking?”. However, if you can’t look back at older photos and cringe, then you probably weren't cool at the time. You are totally meant to have style regrets and not be the guy who always wore a plain polo and chinos in every period of your life.

The three essential things a man should know about style are…

Know what suits you, what you feel comfortable in. For me, maturing means that I am now more comfortable in wearing fewer tracksuits and more tailored clothing in general. Understand colour combinations. If you look great in blue or black, don't push the boundaries too much with colours. Stick to four or five combinations and mix around. Find a good hairdresser. It's so important to be able to groom yourself — but not too much. I think men have probably gone a bit too far with all the waxed eyebrows out there. So, find a happy medium with your grooming regime. Also, have a good tailor around or at least get your clothes tailored at the shops you buy your clothes from.

Do you have any shopping rituals?

I see a lot of things on the runway as well as in the press and I avoid buying full outfits, I go for individual items that I really love and mix them in a hundred ways. I do have a wardrobe of basics from classic brands and then drop in some special items from various designers.

We will never see you wearing...

Never say never, but I don’t think socks and sandals is a combination I will adopt anytime soon. Also, Pixie doesn't like me wearing vests so that’s off the list as well. [laughs]

Which new designers do you follow and why?

Agi and Sam and James Long. Also, A. Sauvage as their collections are amazing, I really love their bold prints.

Who is the most stylish person you have ever seen?

Ryan Gosling has amazing style. He always appears to be so effortless on the red carpet. So cool and easy.

What is the first thing you notice on a man?

If they have a good handshake and whether they are polite or not. Nothing says gentleman like being polite. Always treat the people around you right.

What are the most treasured items in your wardrobe?

All of my Dolce & Gabbana tuxedos, I have so many special memories from the GQ awards. Also, my first Belstaff leather biker jacket and my Gucci swimsuits.

The one image that defined your approach to style...

There isn’t only one, but The Talented Mr. Ripley is definitely a movie that really opened my eyes about how cool the right clothes can make you look like. American Gigolo and what Giorgio Armani did in that movie has also influenced me. It's tailoring but in a cool, casual way that was at that time risk-taking.

Which fashion house never fails to impress you?

Dolce & Gabbana with their slimline Italian suits and Louis Vuitton which is always cool. Both of them really nice.

One article of clothing that a man needs to pay close attention to is…

His jackets, their fit, and shape. It can really make or break an outfit.

Is comfort an enemy of style?

They don't often go hand in hand, but as fashion and functionality are really coming together, I think this is changing.

Who would you like to recommend for My Style?

David Gandy and Sam Webb.

The best words of advice you have ever heard?

Live your life to the fullest and don't let anybody let you down.

Portrait taken at Domes Noruz.

Share this on:   Twitter | Facebook | Pinterest

You might also like:

Flashback with Dsquared2

Flashback with Dsquared2

November 16, 2012
Natasha Slater

Natasha Slater

July 01, 2013
My Style
Dean and Dan Caten

Dean and Dan Caten

September 16, 2014
My Style


September 25, 2012
My Style