Dressing for a Heatwave, Friendship vs. Fashion, and More Dilemmas Solved

We tackle your latest round of style quandaries.
Photo: Everett Collection

Stay cool.

Okay, so the problem now with being stylish in the summer is that it’s so freakin’ hot here in NYC (feels like 100 degrees). So, how can one be stylish on these dog days? Also, where do you guys hang-out after hours? Can I join? Hahaha.
First issue first. You could always try to pull off the shorts-at-work look, and if you want to do that, Nick Wooster has some advice for you. If you’d rather keep your pegs under wraps, ditch the selvage denim for the lightest chinos you can find (Gant Rugger makes a great pair that at least two of us picked up on Gilt), and get yourself some chambray, which is as warm weather-appropriate as it is trendy. The fabric breathes, doesn’t show sweat, and stands up to repeated washing. There’s a reason it’s the attire of choice for chain gangs from South Carolina to Texas.

As for the second question, I’m sworn to secrecy on where the other guys hang out, but a typical after hours scenario at Chez Thoreson involves putting the kids to bed and contemplating cracking a third beer. You’re more than welcome to stop by provided you like The Giving Tree as much as you like ice-cold Peroni.

As it’s getting hotter outside, what would be the best attire or fabric to go with for, say, a lunch or dinner date?
Every man needs at least one good cotton or linen suit in his arsenal. And at this moment on the calendar, either is—much like yourself, no doubt—perfect date material. Both fabrics are lightweight, breathable and quite a bit less dressy than, say, worsted wool. Which is a good thing, because it’s a date, not a job interview. A nicely tailored poplin or linen suit sends the message that you know the distinction between putting in an effort and trying too hard. Wear a pocket square, skip the socks, and don’t forget to hold the door.

Is it possible to be overdressed by association? I’m trying to cultivate my own style, which usually makes my friends look like neophytes (which they are). I want to keep my friends but still dress well. Any advice? — Matt from Philadelphia
Matt, yours is an all too common dilemma (I have one or two old friends with whom I’d rather discuss politics, religion, or yoga poses than style). Sometimes a guy must choose between his wardrobe and his friends. And you know what? You should choose your friends. Because they’re there to keep you in line, whether that means taking away your car keys when you’ve had one too many or giving you much well deserved crap for wearing a pink blazer to a Mets game.

The first rule of dressing well is to dress for the occasion at hand. Sometimes that means patent leather pumps and a tux, and sometimes that means Chuck Taylors and a T-shirt. (Side note: rarely—ever so rarely—does it call for a hybrid of the two.) So skip the pocket square on poker night and focus on setting a subtle, non-threatening example for your fashionably challenged cohort. Start with footwear. Your dear old pal who won’t give up on the square-toes? When he sees you dress up a well broken-in pair of jeans with a serious pair of wingtips, he just may be inspired to ditch the Herman Munster footwear once and for all. You’ll get the satisfaction of knowing you’ve made a difference in the world—and he’ll think it was his idea.

I live in San Francisco, but I’m moving out to Boston in a few months.  I want to get a good pair of sturdy boots (Red Wing 9011, anyone?) that I can walk around with in the snow if I need to, but that also looks somewhat nice.  The only problem is that I’m a pretty small 7 or a 6.5 shoe.  I know that most companies like Red Wing run a little big for my foot, even in a 7, and don’t make much of anything in smaller sizes.  Can you suggest a place or company where I can look to find a good pair that will fit me?
Your case requires me to call in a specialist: my old friend Michael Williams, who contributes quasi-regularly to Gilt MANual, runs the blog A Continuous Lean and handles PR for Red Wing. Sez MW: “The 9011 is too nice of a boot to walk around in the snow with. The 875 would be much better for that purpose (and it runs all the way down to a size 4). So I think he should find something around his house to sell or save up some extra cash and buy a pair of 875s and also pick up a pair of Alden Indy boots—which are sized every way to Sunday.” There you go. Enjoy Beantown.

As a 17-year-old high school student, I am seeking advice in regards to my upcoming senior photo shoot. Simply put, I’m not exactly sure what to wear. I believe I have the option to change clothes and poses four times, with one of those being shot in black and white. Right now, the only thing I’m sure I’ll be wearing is a light gray Ben Sherman suit. I do know that I’d rather these photos not turn out in any way similar to the attached photo. Thanks for your help. –Ricky

Some may fixate on this young man’s hairdo, for me the real tragedy of this photo is the Reebok Phase 1’s. You’re on the right track with the suit. Don’t ruin the look with the wrong footwear. Keep an eye out for Antonio Maurizi sales on Gilt MAN, and pick yourself up a pair of the brand’s cognac wingtips next time one rolls around. Throw in a crisp white shirt, a solid knit tie from Jack Spade, also regularly available on Gilt MAN, and you’re set. Oh, and needless to say, make sure to match your pocket square to the color of your over-sized novelty jacks.

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