So when he showed up for a date looking the way he did, it’s no wonder Michele was less than impressed. “He probably wasn’t,” said my stylish guy friend Will, who’s been divorced for two years.
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. As we age, we tend to wear clothing that’s too big.
A first impression is a lasting one and, once made, almost impossible to change. Your look should be sleek and semi-fitted, which isn’t always easy after 50. Jackets should be contoured and gently hug the body, regardless of your size. It’s no cliché that many if not most women immediately check out your footwear.
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. But if you’re not sure of it, take your cue from well-dressed guys where you live. If it's been decades since you last went clothes shopping, it’s time for a wardrobe update. Your soul might be in Montana, but if your date isn’t, dress to fit the local culture. The hat is really unsophisticated unless you live in a place where they’re the norm. Achieving this may necessitate a trip to the tailor. Not only do shoes have to work with what you’re wearing, but they also have to look like they’re cared for.
And the following classic suggestions will help you look great for any date. And the best way to do that is invest in a few timeless classics. And a cap screams Peter Pan, especially if you wear it backward. She’ll notice whether you notice, and take care of, the details. 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. Forget readers or bifocals with a line across the width of the frame.
She thought he’d be stylish because of his French heritage. The two met online, and Michele liked the photo of him in a pressed shirt and the fact that he was French.
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.
A Francophile, Michele appreciated that culture’s easy stylishness and had spent many vacations in Paris, especially after her divorce a dozen years ago. Born in France to a French mother and American father, from the age of 7 he grew up in the United States.
Most of the French men she’d seen had a great look: well-fitting pants, shirts, jackets … 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.