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I have a basic question for you: Can a guy wear a Hawaiian shirt and still be considered well dressed? Is there any setting where this is OK? I’m trying to understand where the line between “wacky uncle” and “summer casual” is drawn.
The short answer to your question is that no one is going to consider a man in a Hawaiian shirt well-dressed. They’re kitschy! They’re colorful! They have huge flowers on them! Chunk wore one during the Truffle Shuffle! It’s not exactly a dignified look. But that doesn’t mean that you can’t wear one. Though I love classic style, I also love eclectic elements incorporated–in moderation–into a wardrobe. Are Hawaiian shirts my favorite? No, but I also don’t want to see everyone walking around wearing the same thing–boring! I realize this column, and Dappered at large, have been dedicated to classic, elegant style, but the more questions I get from readers, the more I realize that the best part of style is seeing what other people come up with, especially if it’s different from your own aesthetic. If I insist that all of you wear pressed pants and slim fit button downs and navy blazers day in and day out, we’ll all die from boredom. Boo! It’s the kilt-wearer and the ascot-mascot who make fashion fun. So I’m going to give you some pointers on wearing a Hawaiian shirt in case you decide Frank Sinatra-be-damned, you’re giving this look a whirl.
The wide scope of the the Hawaiian shirt. Moving left to right: Seriously? –> As a heart attack
Style in this particular arena is tricky in that it works if it is intentional, but not if it isn’t. Gotta love a double negative. Here’s an example that might illustrate my point: ripped jeans. Woman A is wearing light blue jeans whose waist rests midway between her armpits and belly button. The butt of the jeans is saggy, the crotch of the jeans is too tight. The jeans are a bit shredded around the knees and thighs, and there is evidence that this woman does oil changes in her spare time. Woman B is wearing very dark blue jeans whose waist rests just below her belly button. The butt of the jeans is form fitting, the crotch of the jeans is smooth and flat. The jeans are a bit shredded around the knees and thighs, but are otherwise spotless. Both women are wearing ripped jeans, but one is wearing them because she doesn’t care, and the other is wearing them because she does.
This is how you approach tricky style quandaries like the Hawaiian shirt. It needs to look like you meant to wear it, not like you dug it out of Frank Costanza’s attic. This means it should be in good condition, and it should fit appropriately. The Hawaiian shirt is cut to be worn a bit bigger and baggier, so try on several different sizes besides your normal in order to get a fit you feel comfortable with. Who knows, maybe you’ll be a pioneer in the slim fitting Hawaiian shirt.
As you mentioned, setting for this look is crucial. Backyard barbecues, pool parties, walks along the beach–are you seeing a trend here? Warm weather only, casual setting only, outdoor activities only. Wintertime, your wedding anniversary, dinner out–don’t you dare. If you do, I’ll sense your transgression in my bones and then I’ll have no choice but to hunt you down and shame you. With the cone of shame, naturally.
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