Is there a growing gap between what designers are making and what regular men are willing to wear? Is there a growing disconnect between menswear designers and men?
-Jon S.
I think that each season the same debate is always present about whether designers are making clothes that regular guys are comfortable wearing, and my answer to this is that you always have the ability to wear pieces from different designers that fit your style.
I love Thom Browne, but the only thing that fits me are his ties; the same goes for Dior, as I can really only fit in the jackets and tops. This is a key to making your wardrobe work even if you feel like the runway isn't working for you!
Are you as irritating to sales clerks as you are to opposing players?
The worst thing about sales clerks is when they are too pushy. When that happens, I move on to the next store!
I live in NYC and I am 30 years old. Most of my first dates are drinks at nice lounges or wine bars, and I usually put on a funky pair of jeans, cool button-down and white trendy sneakers, i.e., Prada, etc. I like the sneaker look but I am now wondering if that is a turnoff to women being that I am now 30? Should I just be myself and continue to show my personality through my funky sneakers or should I start to play it more conservative with a dressier shoe and look?
Thanks,
Daniel
The sneaker debate with jeans is always a point of concern -- keep your sneakers clean and have them match a piece of your outfit. If you have a white dress shirt on, try not to wear a red shoe; if you wear a black shirt, don't wear a white sneaker.
I love wearing sneakers with jeans, but I don't recommend the New Balance runners with jeans. You may as well write “banker” on your forehead.
What’s your ideal first-date outfit?
I feel like your first date attire should never be more than jeans, T-shirt with boots and a leather jacket. Even if you’re not cool, you should at least try and look it to see if you can get the second date. Always underdress on a first date.
5. What’s the simplest way to update your look without breaking the bank?
The best way to update your look is to be smart where you spend your money; go and get your cashmere sweaters at Uniqlo instead of Prada. This allows you to spend the important dollars on a new pair of driving shoes, which are my new obsession. The money should be spent on jeans, jackets and dress shirts.
6. What's your take on leather coats over suits? I'm currently looking at a brown leather (I believe calfskin) coat to wear over my brown suit, but seeing as I'm usually a pretty fashionable man and this coat will set me back a pretty penny, I have to know if it'll work to save face and money.
-Contemplating in New York
Unless you’re Shaft, do not ever wear a leather trench coat over a suit or your pajamas... Jesus.
7. I have a question that pertains to shoes and belts. I seem to have a difficult time finding a belt that matches my shoes, or vice versa. Do the belt and shoe have to be the same color or can one be a couple of shades off?
Thanks,
Adrian
Your belt just has to be in the family -- it can be any shade of brown or blue. The only rule I have is never wear a white belt with white shoes.
Actually, don't ever wear a white belt ever!
Winter is on its way, men, so start wearing a lot of black -- you really can't f*ck that up....
Peace & Love,
Sean
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