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Men's Style: What to wear on a date…
Man starting over needs dating wardrobe

I find myself looking at dating again, and it's a little scary... mostly when I look in my closet. After 24 years of marriage, my wife passed away and I don't know what to wear on a date.

It's been almost 30 years since I've had one. I'm 50, in good shape, with a V body: 34 to 35" waist, 45" chest. I want something stylish, but am having a hard time picking out casual clothes that aren’t jeans, or end up being not casual enough. It seems that the clothing I like is really for a younger man, 25 to 30 or so.

Can you help with some suggestions and perhaps stores to try? Thanks, I’m tired of being the 3rd wheel! (Clark, NJ)


While most folks find it scary to begin a new chapter, you find your personal fear factor in the guts of your closet. My sincere condolences about your wife’s passing and applause for having the courage to start out fresh again.

First off, having a killer V-body at age 50 is pretty darn hot, so do choose clothing that suits a more athletic physique. Dressing for your body does not necessarily mean dressing young.

I’m not sure about what you think looks more appropriate for a 25 to 30 year old guy, but style is not about age, but how the clothes hang on you. If form fitting clothing looks great, go for it. Stay away from obvious teenybopper fads and opt for a cleaner, sophisticated design in a similar style.

Well-fitting jeans are a great anchor for a casual night out. Pair them with a single breasted dark jacket and a sport shirt in a gorgeous color for a nice, relaxed dinner first date. Keep the baggy jeans for kicking a football around. A flat front, relaxed fit cargo pant paired with an untucked tee and a graphic print sport shirt worn as a overshirt is a solid sporty look. On a dressier date, try a dark suit (you borrowed the jacket to wear with jeans) and forgo the shirt and tie for a simple pima cotton sweater or vivid stripe shirt unbuttoned at the neck.

There are so many choices to shop, both online and brick and mortar. What you want is to find a store with an overall style which appeals to you. At times, it’s easier to start our in an environment where everything is merchandised to work together, like a Banana Republic, rather than a small boutique with specialty items. What counts is that you feel at ease shopping there and there is a sales staff available to help you if you need them.

Remember that clothes do make the man, but a woman dates a man who she has fun with, respects, admires, and finds engaging. Spend some time in stores to check out different looks, but spend more time enjoying life as a whole.

--January 24, 2005

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