What Should a Guy Have in His Wardrobe?

Dear Lovesick Billy,
I’m a recently divorced man in his 30’s, who’s getting back out into the dating world, and I need a few pointers on what I should have in my wardrobe. Any ideas?

  • Role Models – Celebrities enjoy the benefit of stylists, and you can too, by emulating the styles of celebrities whose style you like, and who have a similar body to yours. David Beckham? Tiger Woods? Eddie Izzard? If their style suits you, knock off what they have on and once you’re comfortable with that, develop it into your own style.
  • Good Denim – Basic denim that suits your shape is crucial, and it doesn’t have to be exotic or cost a fortune. If you’re the Abercrombie body type, the fashion world is your low fat oyster, save yourself the trouble and simply remain naked at all times. For regular guys, a regular rise, not too baggy, not too tight. Trendy jeans are fine if you’ve lots of cash to spend when the trend changes. Classic never goes out of style. Great jeans, a nice pair of shoes and a collared shirt and sweater or jacket, and you’re set for most occasions, including a lot of workplaces these days.
  • Good Shoes – Indulge your inner Sarah Jessica Parker and score some good shoes. They don’t have to cost a fortune to look great and be comfortable. Zappos has crazy selection at the best prices around, and Aldo makes some great stuff too. They don’t have to be boring either: a stylish black lace-up, a rich brown or oxblood, and in styles that look good with your suits as well as jeans, and you’re set.
  • Black Underwear – Simply put, briefs are sexy. The right size and a little lycra will go a helluva long way to making you look better in less. What’s the right size? Your stuff should enjoy some firm support and not be lost in the wide open spaces of the front, and the ass shouldn’t say ‘granny’. The best advice? Buy all black underwear and never face a skidmark again. If you like the big impression of pitching a tent in a pair of boxers, save those for special occasions and keep them white. Seasonally patterned boxers are cute for only a minute, unless they were a gift from the person you’re peeling down to them for. Dingy drawers are for guys who don’t like getting laid.
  • Age Appropriateness – A&F models are twenty-something at best because that’s the demographic – for a reason. If you’re in your early thirties and so is your waist, you might be able to pull it off, but know your limits. Mature men in young printed t-shirts look like unsuccessful chicken hawks. Move on. Don’t be sad. Good labels that A&F punks can’t pull off or afford await you.
  • Jackets & Vests – Vests that were or are a part of a 3 piece suit are an invaluable addition to the old button shirt/jeans combo. Look at Becks. Jackets are equally valuable. Nice fabrics and classic cuts that aren’t ironic will never steer you wrong. You can often find good suits and tuxedos in consignment and second hand stores. Get a nicely styled, single-breasted jacket that fits, and the pants will likely be 40” waist and a 25” inseam. Chuck ‘em. You just want the jacket. If it’s a little big, take it in to be tailored and dry cleaned. Be a snob on this: good designers will likely have better lines than the Stafford Collection from JCPenney.
  • Two Good Suits – Black, Charcoal, Glen Plaid, Dark Olive, or Dark Navy. Two or three buttons, single breasted. Good proportions and a nice feel to the fabric. Bear in mind that with the exception of the glen plaid, most of these will go great with jeans too. Macy’s kills every other store twice a year or more, with their killer sales. Stalk a good label until it’s on sale for the right price vs. buying a cheap label. You won’t be sorry.
  • Plain T-shirts – Printed t-shirts, with little exception, are made to promote things and turn you into a billboard. Plus, they’re two years ago. You’re promoting your own brand now, one that doesn’t need clever slogans to say who you are. It’s hard but you can do it.
  • Fitness – The most expensive designer clothes will look like laundry bags if you’re not putting your best body into them. Looking good in clothes is not the reason to get or stay fit, but a healthy man looks better in everything.

I’m not going to tell you to have fun with it. It’s not always fun. It can be very frustrating, and we’ve all been there. Hang in there, show yourself some love and have confidence in what you choose. You can’t lose.


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