ASK DAN: Combovers, Beltlessness, Short DBs

March 17th, 2015


Q: My dad has no sense of fashion. He’s also been rocking the worst comb-over in history for about the past 10 years. How do I convince him to trim it off, and step up his style game in general? I try and be a good influence on him, but some people are just set in their ways.

A: Find that man a good hat. A combover means he doesn’t have a lot of hair and is self conscious about it – which is a good sign because it means he cares, to some degree. Finding a flattering hat can change all that, so take him to a headwear expert and let him see the difference. As far as getting him on board with a full-on style upgrade, make a bet with him, and convince him that if you take him shopping (including the tailor and the barber shop) and get him a new look, he will feel better and people will be complimenting him like never before… Then prove it!

Q: Tips on going beltless? I know it’s a good look if you can pull it off but I always feel incomplete without one, like I didn’t finish getting dressed before I left the house. Is it okay to do it with slacks that still have belt loops?

A: The first tip is making sure the waist on your trousers fits properly so you don’t need a belt to keep them up. I rarely wear empty belt loops…most of my trousers are designed to be worn beltless, with side of rear adjusters. It’s more comforting knowing that there is some mechanism to ensure your trousers stay in place. The other option is sewing buttons to the inner waistband and experimenting with traditional braces. A lot of guys fall in love with them, because of the comfort and the hidden element of style. 

Q: I love the elegance of the double-breasted jacket, but I’m a small guy (5’7 on a good day). Can short guys pull-off the DB look? What’s the secret?

A: Sure, but the cut has to be just right. When I won Esquire’s “Best Dressed Real Man in America” one of the finalists was a very small guy (I would say maybe 5’3) who wore some incredible double-breasted suits and jackets. He has a combination of confidence and knowledge about his wardrobe, and a great bespoke tailor who makes sure the armholes are high, the lapels lift the shoulders, the midsection is as trim as possible, and the body is just long enough to cover the seat. Check him out here

Got a style question? Hit me!

Thanks, as always, for reading.

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


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