Shipping to
United States
Shop The Story
Photography by Mr AJ Numan | Styling by Mr Tom Stubbs
Words by Mr Simon Mills

The navy blue padded gilet and sweatshirt combo isn't quite doing it for Mr Seán Dermot Fintan O'Leary Jr. His stylist, Mr Tom Stubbs, tries to talk him into wearing the sleeveless garment for our photo shoot, but the team reckons it looks a bit too Back to the Future. The Essex-born Radio 2 DJ and The X Factor host grimaces at this reference and removes the offending item. Now he's in a Paul Newman-esque waxed cotton car coat, a well-cut pair of chinos and some simple brown lace-ups. Much better; much more Mr O'Leary's style. He's happy now, and after a quick fiddle with iTunes (lots of King Creosote, Madness and Morrissey) the photographer can start work again.

The closer Mr O'Leary gets to his impending wedding day, the fussier he becomes about his clothes. Certainly, the rugby playing, James Joyce-reading Arsenal fan has come a long way from the football terrace gear he wore when his career began on Channel 4's T4 show 10 years ago. Now a primetime TV mainstay, Mr O'Leary prefers to look the part in super-sharp tailoring with a carefully folded handkerchief in the jacket breast pocket. "Just because it's Saturday night, it doesn't have to be bling or shiny," he says. Here, Mr O'Leary shows what ensembles manage to make the cut.

Your style has changed quite a bit over the past two years. Sharper, more dapper suits with narrower lapels and slimmer trousers...
I've been on TV since I was 25, and I am 38 now. You just evolve, don't you? Which is only natural, as I really should not be dressing the same as when I was 25. I think you just get to a certain age when you start caring much more about the way you look. When I first started my TV career I would get loads of clothes sent to me for free and I would just be grateful they'd arrived. Now I'm a bit more discerning, I hope. I tend to be quite critical of the way I look.
What was wrong with the way presenters dressed in the past?
What I love about Gary [Barlow] being on The X Factor this year is that the shiny suits of garish Saturday night TV wardrobes aren't there any more. Both of us are flying the flag for proper tailoring, which I think is cool. It's nice that boys are reclaiming the clothes thing now.

Everyone goes on about Steve McQueen but for me it was always Paul Newman. McQueen was tormented and chippy but Newman seemed so sanguine, cool and at peace with himself

Aren't you a little jealous when The X Factor judges do their starry walk-on at the beginning of each show and reveal their outfits?
Not really, because I get the spotlight, head to toe, for the whole show. After we've wrapped, I've noticed that Gary gets out of his suit pretty quickly but I like to stay in mine all night.
What's the secret to good style?
It has to fit. I now realise that having a suit that fits properly makes such a difference, especially for TV. It actually makes me look taller. I love Acne, Spencer Hart, A.P.C. and Paul Smith; with shoes it's Grenson and J.M. Weston. Women are always going on about the importance of a good pair of shoes, but it's not until you get your feet into a well-made pair that you realise what they are talking about.
Who has, over the years, influenced your style?
My dad. He is the greatest schmoozer on earth. He was a hurling champion who came to England from County Wexford with only £30 in his pocket. He encouraged us to read up on Irish politics, James Joyce and Brendan Behan. When I was a kid I was into The Pogues and Bruce Springsteen, but I never aspired to dress like them. I grew up in Colchester, which was close enough to London to be influenced by it. I love clothes but I haven't always been able to afford them, so I was one of those guys into football casual gear. I wore whatever I could cobble together from Topman. Then I started playing rugby... Thank Christ I never went down the rugby boy-style route, which has never been a good look. The great thing about London is that you don't have to be wealthy to look stylish. There are all sorts of ways of getting a look together that won't cost a fortune.
Is there an age at which a man should stop wearing sneakers?
No, because no matter how old, a guy can always rock Jack Purcells, can't he?
Professionally, you live quite a schizophrenic life. The music you hear on The X Factor is not the sort of thing you play at home or on your Radio 2 show...
I know what you mean. At the moment I'm listening to stuff by We Are Augustines, Lana Del Rey and King Creosote. But, there is a bit of crossover sometimes. Last year, I put out an album of songs from my radio show called The Saturday Sessions, which had a slowed-down cover of Michael Jackson's "Thriller" by Imogen Heap on it. The people at Simon Cowell's Syco office heard it and went crazy; Imogen's take on the song ended up being covered on The X Factor by Aiden [Grimshaw]. I'm not going to walk on afterwards and say, "By the way, that's from my album," but I was proud as punch.
What's the secret to being a good interviewer?
Never treat anyone as if they are more or less important than you.
You are one of those rare TV personalities that appeals to both men and women. How come?
I think blokes like me because I'm short - only 5'9" - and not especially good looking.
You recently announced you are getting married to your long-term girlfriend, TV producer/director Ms Dee Koppang. What took you so long?
We've being going out for more than nine years. Yeah - long time, I know. All our friends have been putting a bit of pressure on us for a while. We thought the secret of our success was that we spend a lot of time apart. For the first five years I spent quite a long time away, and then for the past four years she's been away a lot, so there has never been much consistency in our relationship. But when we are together we have great fun, so I decided it was time to do something positive. It was all fairly traditional. I asked her parents' permission beforehand and then took her to New York and proposed in a restaurant called Saxon + Parole in Manhattan's NoHo.
So, the big question is, what are you going to wear on the big day?
Well, I'm not doing the morning suit thing but I want to have a suit made. I think I'll work up a few ideas with my stylist, Tom. We have a lovely relationship. I didn't want someone who just told me what to wear. I wanted to find a stylist I could talk to and occasionally have a bit of conflict with, and that's who Tom is. He's a great character - he really should be on TV.
Whose style do you admire?
When you are growing up it tends to be anyone who is on TV, doesn't it? I used to like the way George Peppard looked on The A-Team, for instance. I like to learn about the heritage and origins of certain items of clothing, find out who wore what first, and why. Everyone goes on about Steve McQueen but for me it was always Paul Newman, especially in Cool Hand Luke, The Hustler and Somebody Up There Likes Me. McQueen was tormented and chippy but Newman seemed so sanguine, cool and at peace with himself.