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Wearing Shorts in the City: Ever Okay?

The latest in an ongoing series in which we debate current style topics with an intensity that is—we'll be the first to admit—a little out of proportion to the actual significance of the issue at hand.

Photo: Everett Digital

Evan Rachel Wood explains the shortcomings of short pants to Larry David in "Whatever Works"

On Apr 22, 2011, at 5:44 PM, Andy Comer wrote:
Tom Ford says a lot of things in the current issue of Another Man. Here’s one I happen to agree with. In response to the question, “Should a man ever wear shorts off the tennis court?” Ford says, “No. Absolutely not. If I’m on holiday, occasionally I’ll put on a pair of shorts with my T-shirt and go barefoot with my towel down to the beach…But in the city? Never. That’s an American thing, which I just don’t get.” Okay, so maybe the tone is a wee bit condescending. But I don’t get the appeal of shorts, either; and I’m not looking forward to this particular wardrobe item’s return to the streets of New York, where I must concur they have no place at all. And with that I declare Reply-All in session…

On Tue, 26 Apr, 2011, at 11:09 AM, Tyler Thoreson wrote:
I grew up in Minnesota, land of 10,000 lakes and five-month winters. The kind of place where, when summer finally comes, you feel compelled to make the most of it. To me, that means showing a little leg as soon as temperatures rise into the 60s. Admittedly, I don’t wear shorts much in the city these days, but I don’t see anything wrong with taking a Saturday stroll in the West Village in say, an untucked linen shirt, a nicely broken-in pair of loafers or bucks (sans socks), and a good old pair of cutoff chinos. In fact, I think I just finalized my weekend wardrobe.

On Tue, 26 Apr, 2011, at 11:48 AM Jared Flint wrote:
I would normally fall squarely in the no shorts in the city crowd. But there’s some pretty big caveats out there. Shorts should never be worn to the office, any meal, or out at night. Basically any place or setting where you wouldn’t wear a baseball cap. Yet, there have been some occasions when wearing pants in the city was just a recipe for contrived sweating. Rooftop parties in July and August? Those are boiling and shorts are entirely appropriate. All Points West, Williamsburg’s Pool Parties, Governor’s Island, or Lollapalooza for our Chicagoans are all sweat-soaked daytime music scenes squarely within urban confines where shorts may just help in avoiding heat stroke. I bring these up because my heart is with the pants argument, but the facts on the ground just don’t back it up.

On Apr 26, 2011, at 2:39 PM, Josh Peskowitz wrote:
I made the mistake of wearing shorts to the office once, in my halcyon youth. My editor at the time walked by me, did a double take and said “Christ Peskowitz, what are you going to do Monday, wear a Speedo?” He had a point, shorts have no place in the office, or anyplace else once the sun sets, but I can’t categorically ban them as Mr. Comer would. Here’s the key: Length. A grown man can not and should not wear shorts that go farther than halfway down the knee. Above the knee is generally preferable. They are not for every occasion, but there are times (the aformentioned roof top jams, trillions on the thermostat, weekends in the neighborhood) where, when worn with a crisp polo and some vans, a pair of shorts will do you very right. It is an American kind of thing, and should be used sparingly, but can be a damn fine look.

On Apr 27, 2011, at 4:32 PM, Andy Comer wrote:
Not sure I buy the “functionality” argument for shorts. Yes, summers in New York City are brutally hot and humid. But that doesn’t mean we’d get behind tank tops or mesh shirts or, worse, wearing no shirt at all in public under those or any other conditions. And yet we feel obliged to defend a garment that until the late twentieth century was identified primarily with preadolescence. With all the great-looking, great-feeling summer fabrics out there—cotton, linen, seersucker—is it really so hard for a man to put on a pair of pants before he leaves the house?

On Apr 27, 2011, at 4:46 PM, Christopher Wallace wrote:
Arguing with you on this point is more difficult than backpedaling down stairs in flip flops (which I won’t be doing). But what if we carve out a compromise? What if we say no, absolutely not, to anything mesh, remotely athletic, baggy or below the knee at any hour of the day, but allow for something tailored, at least 1″ above the knee, worn within sight of a body of water, booze, bikinis or a barbecue between the hours of 10am and 6pm?

On Apr 27, 2011, at 5:14 PM, Andy Comer wrote:
You’ve awakened my diplomatic side!

On Wed, 27 Apr 2011, at 4:17 PM, Christopher Wallace wrote:
Don’t worry, I won’t go all Henry Clay over flip flops.

On Apr 27, 2011, at 5:24 PM, Jared Flint wrote:
Finally, a reference to the Great Compromiser in Reply-All. So, mesh shirts and baggy cargo shorts = Seward’s Folly?

On April 27, 2011 at 5:40:59 PM Tyler Thoreson wrote:
You and your fancy book learning remind me of this fine image from Take Ivy.

Photo: A Continuous Lean

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  1. Igael says:

    i agree with Josh, length is key! one should not wear shorts that go farther than halfway down the knee. Indeed there are times when its hot and your not going to the office (its the weekend or a day off) and pants can be a bit much, so worn with a polo shirt, a boat shoe or a loafer it looks great. I don’t think its an “American” thing. Ive seen this look done very well in Paris and Rome.

  2. David says:

    i just bought a pair of +J Uniqlo long shorts (yes, falls well below the knee – GASP!) and they are quite fetching. Of course, I can roll them up but I like the length. Reminds me of what the chic Europeans wear.

  3. James says:

    As much as I want to side with AC, it’s still NYC in 2011. Mid July can get brutal (last summer being a great example and btw, I’m strictly a trouser wearer year round) but JP and CW hit it right on the nose. There should be some kind of leeway but at the same time acknowledging when and where shorts are acceptable. Great job, boys.

  4. Anonymous says:

    I don’t know what universe Andy is living in. Not sure you buy the “functionality” argument? It reaches 90+ degrees and 100% humidity at least a few days every summer in New York! To say nothing of Washington, Atlanta, or the other hotter cities. Suggesting that “summer fabrics” are a remotely effective away to deal with that heat is intentionally oblivious. You would be an order of magnitude hotter, sweatier, and more uncomfortable in seersucker pants than you would be in even thick wool shorts – and by the way, you don’t have to choose between summer fabrics and summer-length lower coverings. You can get linen shorts. You *should* get linen shorts.

    Obviously, shorts are off-limits at most offices. (I work next door to the Facebook offices, so that’s a different sartorial story – but I digress). But anywhere else, on one of those especially hot summer days if I see a guy in trousers (even if linen, seersucker, etc.), one of my first thoughts is, “Poor guy, he must be hot.”

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