FROM OUR JANUARY ISSUE: SEPARATING THE MAN FROM HIS CLOTHES

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When I was young and dating, and my mother would ask how the date went, I’d describe what the guy was wearing—and why his “outfit” would definitely preclude a second date. As a fashion stylist and writer, I gave no second chances to guys wearing too-tight jeans or Bermuda shorts at a somewhat fancy cocktail bar.

My mom would admonish me: “You can change the clothes but not the man; if you find a good one, give the poor guy another shot.” Older and wiser now, I completely understand what she meant. If you’re lucky enough to find a guy who loves, respects, and is there for you as a romantic partner and/or best friend, does it really matter what he wears?

Eventually, he’ll give up his socks with holes and maybe even his favorite team sweatshirt, a garment so threadbare you can barely make out which team it once celebrated. Eventually, he might even take your not-so-subtle hints about more fashionable wardrobe alternatives. These days, most of the men I date aspire to dress like a pop star, be it Bruno Mars, Chris Martin, or Bruce Springsteen, depending on their age. Worse still are the guys who dress like Brad Pitt in his “colorful” outfits – all perfectly styled for Brad but clearly wrong for the finance guy or environmentalist lawyer you might be dating.

So, how do you separate the guy from his clothes? As my mom tried to tell me, don’t make snap judgments. Always go on the second date, and if he’s wearing puka shells and a Hawaiian shirt, then ask if he’s planning to jet you to a tropical island for dinner. If he laughs at himself and your humor works, score a point or two for him. Another option: suggest a fun shopping day!

Okay, fun isn’t usually in a guy’s vocabulary when it comes to clothes shopping, but it can happen. It’s all about the delivery or what you promise him in return. While shopping, suggest a well-cut sport coat in navy, black, or grey, a solid or patterned woven shirt, and a longsleeve crew, V-neck, or quarter zip in fine gauge cotton or cashmere. If he’s dead set on jeans, remind him that after a certain age, a relaxed fit is more flattering and more comfortable than jeans glued to the body, except if worn by The Boss himself.

(Yes, this Jersey Girl is a big Springsteen fan!) Although fashion from the 1960s and ’70s (exuding an anti-establishment or disco vibe) is very much in style these days, looking like a hippie or like you stepped out of Saturday Night Fever is best reserved for those who weren’t around to wear these looks when they were first in style.

As for the guy who loves Hawaiian shirts, invite him for a luau-style dinner, wear a lei and flower in your hair, and try and get to know the man beneath the clothes. (My mom is surely smiling from heaven.)

Beth Bernstein is a freelance writer specializing in fine jewelry and contemporary culture.