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Single, Male and Clueless How to Dress for a Date? Here’s Help

A foolproof guide to making a positive first impression when you're back in the dating game

She thought he’d be stylish because of his French heritage. But when Michele M. met Roger B., he was anything but. A widower in his 50s, clad in faded, acid-washed and roomy jeans, a baggy T-shirt and scuffed running shoes, he looked like he was ready for a game of pick-up basketball rather than a cappuccino and conversation with a lady.

The two met online, and Michele liked the photo of him in a pressed shirt and the fact that he was French. A Francophile, Michele appreciated that culture’s easy stylishness and had spent many vacations in Paris, especially after her divorce a dozen years ago. Most of the French men she’d seen had a great look: well-fitting pants, shirts, jackets … some even wore ascots.

Then there was Roger. Born in France to a French mother and American father, from the age of 7 he grew up in the United States. During his 27 years of marriage, his wife had chosen all his clothing, but since her death a few before, he’d taking to dressing, shall we say, rather haphazardly. So when he showed up for a date looking the way he did, it’s no wonder Michele was less than impressed.

So what was he thinking?

“He probably wasn’t,” said my stylish guy friend Will, who’s been divorced for two years. Although he doesn’t know Roger personally, he knows the type. “Many men, especially those who haven’t been on the market for 20 or 30 years, have no idea how to dress for an actual date — especially if it’s a casual meeting. They don’t realize that as much effort has to go into dressing casually as professionally.”

What you wear can be as important as what you say when you want to make a favorable first impression on a woman. If you don’t look successful and confident, you may not get a chance to wow her verbally before she summarily decides she doesn’t want to get to know you.

To make matters even more challenging, you have only a blink of an eye to express yourself visually. A first impression is a lasting one and, once made, almost impossible to change. But if you’ve been dressing for comfort rather than for dating success for the past years, or decades — or have relied on a woman to make your sartorial selections for you — fear not. Every region has its own unwritten dress code. But if you’re not sure of it, take your cue from well-dressed guys where you live. And the following classic suggestions will help you look great for any date.

7 Foolproof Tips to Dress for Dating Success

1. Modernize your wardrobe. If it's been decades since you last went clothes shopping, it’s time for a wardrobe update. And the best way to do that is invest in a few timeless classics.

  • A long-sleeve cotton shirt with a collar in some shade of blue, solid or patterned, that fits as if it were custom-made. Women are attracted to men wearing blue, says color consultant Leatrice Eiseman, director of the Pantone Color Institute and the author of Colors for Your Every Mood. “Guys who frequently wear blue are stable, faithful, constant and always there,” she says. “The ‘blue guy’ is a fantastic candidate for a long-term relationship: He’s dependable, monogamous and can match his own clothes.”
  • A pair of flat-front, non-cuffed pants in khaki or gray (or both). Pleated pants make any man look fat (and they’re not hip), plus, unlike flat-front pants, they are traditionally worn cuffed, which can make you look shorter.
  • A two-button navy sport jacket: It never goes out of style and is almost universally appropriate. Avoid brass buttons unless you have a really big yacht and are taking her out on it. Landlubbers should stick with horn, black or gray buttons.
  • A pair of black or brown loafers or boots (brown if your pants are khaki, black if they’re gray). You can wear brown loafers with gray pants, but you shouldn't wear black loafers with khaki.
  • A pair of dark denim jeans that hug your hips and butt and do not flare in the leg, ideally with a moderate a boot cut.
  • A new leather or skin belt with an unobtrusive buckle that matches your shoes.
  • If your style is a little edgier, substitute a lightweight sweater or long-sleeve T-shirt for the dress shirt, black jeans instead of dark blue for the trousers and a leather jacket for the sport jacket.
  • If all this sounds like Greek to you, make an appointment with a personal shopper at a department store, an image consultant or a sharp-looking salesman at your local men’s shop.

2. Don’t wear a cowboy hat. Your soul might be in Montana, but if your date isn’t, dress to fit the local culture. This goes for baseball caps, too. The hat is really unsophisticated unless you live in a place where they’re the norm. And a cap screams Peter Pan, especially if you wear it backward. You are now a grown-up. Dress like one.

3. Wear clothes that fit your body. As we age, we tend to wear clothing that’s too big. Your look should be sleek and semi-fitted, which isn’t always easy after 50. Shirts shouldn’t bag; pants shouldn’t sag. Jackets should be contoured and gently hug the body, regardless of your size. Achieving this may necessitate a trip to the tailor.

4. Polish your shoes. It’s no cliché that many if not most women immediately check out your footwear. Not only do shoes have to work with what you’re wearing, but they also have to look like they’re cared for. She’ll notice whether you notice, and take care of, the details. That says a lot about you.

Be sure to match the correct shoe type to your outfit. With suits, wear lace-up shoes, unless you are foregoing a tie — then you can get away with dressy loafers. With slacks and a sport jacket or any casual pants and a shirt, wear low boots or slip-in shoes, like loafers. Save deck shoes for the boat or beach, and sneakers for the gym. Pop quiz: Should your socks match your pants or your shoes? Correct answer: your pants.

5. Sport cool eyeglasses with transitional lenses. Forget readers or bifocals with a line across the width of the frame. Get contact lenses or really cool frames with progressive lenses that flatter your face. These days, glasses are stylish accessories as well as necessities so don’t settle for anything less than spectacular. Classic, Clark Kent–type black plastic frames are chic now, so if you have them, even if they’re years old, flaunt ’em.

6. Look good enough to touch. You’ll seem appealing and successful wearing fabrics that feel good and look like they do: buttery leathers, cashmere, fine-gauge woolens, Egyptian cotton, worn denim, flannel, soft linens and the like. High-quality, high-touch garments are a sound investment.

7. Smell good. Of course, you want to begin with clean skin and clothes, antiperspirant and mouthwash. But a finishing spritz or slap of a lightweight scent is a good thing and one known to attract others. Dr. Alan Hirsch, director of the Smell and Taste Treatment and Research Foundation in Chicago, conducted research on behalf of AXE body products to determine women’s scent preferences in 10 different cities. Guys, take note:

  • New York: coffee.
  • Los Angeles: lavender.
  • Chicago: vanilla.
  • Houston: barbeque.
  • Atlanta: cherry.
  • Phoenix: eucalyptus.
  • Philadelphia: clean laundry.
  • Dallas: smoke/fireplace.
  • San Diego: suntan lotion/ocean.
  • Minneapolis/St. Paul: cut grass.

Don’t laugh: Our olfactory sense is our stronger, triggering powerful memories, often from our childhood, which is why it still can affect us later in life. Be guided by the above selections or seek out one of your own and try it — just don’t apply it too liberally.

Style and communications coach Susan Sommers, founder of Dresszing.com, helps people achieve success by looking and acting the part.

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