In Praise of the Traditional American Sack Suit

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Last week, I was fortunate enough to attend a very nice whiskey tasting and dinner hosted by a brand I like very much at an extremely upscale private club in Manhattan. As I was leaving my office for the event, a co-worker asked where I was going, and when I told him, he said, and that’s what you’re wearing?

Now, because you must be wondering, here is what I was wearing: these slightly cropped, fairly wide-leg pants and a well-fitting, very soft button-up, both from Madewell, along with my favorite new chore coat of the year, the French Moleskin Work Jacket from Le Mont St Michel, in forest green. For shoes, I wore these Grant Stone Plain Toe Dune Chromexcel bluchers, which I’ve had for years and recommend to people all the time.

I knew that I was leaning more toward classic workwear than the tailored looks I now feared would dominate the room. They didn’t, though. Because we are in the year 2024, most of the men in attendance were wearing what looked like technical office pants and quarter-zips over non-iron button-downs. There were some sharply dressed folks, no doubt, but…Pitti Uomo this was not. Once I arrived, I felt perfectly comfortable and appropriately dressed. Even later in the evening, when Leonardo DiCaprio and Tobey Maguire set up shop at a table across the room, I did not suddenly feel a wave of embarrassment wash over me. Go figure.

But, rewind to when I was leaving the office. The co-worker I mentioned earlier told me I should consider bringing a suit into my office to have on hand for situations like this when they arise, as if I was simply caught off guard and hadn’t just made a personal decision to dress a certain way.

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It did get me thinking about my relationship with suits, though. I’ve always liked them very much, and at various times in my life, I think I’ve worn your standard J.Crew Ludlow and Brooks Brothers 1818 Regent Fit suits reasonably well. Every time I wear one, someone tells me how tall I look. They make you stand up a little straighter, feel a bit more important or powerful or something stupid.

But I’ve also never quite felt like myself wearing a suit. I came up in an era where the counterculture being what it was sorta mandated that you would not be caught dead in a suit if you could help it. I’ve overcome that hangup for the most part, but it does still feel like a code I’ve yet to crack in a way I feel fully proud of.

I went through a phase at some point around 2011, when, like so many others, I became obsessed with traditional Ivy style. And I don’t just mean I’d been listening to early Vampire Weekend a lot or that I’d watched Mad Men. I was on all the forums (Ask Andy, anyone?). I was buying secondhand Harris tweed blazers off of eBay. Lusting after cordovan Alden longwings. Stocking up on rep ties. Worrying about whether I had the appropriate collar roll on my OCBDs.

Out of nowhere, and at a time when I didn’t even realize they were still making it, I got an email from Brooks Brothers yesterday morning about their No. 1 Sack Suit, which is one of the more iconic items in the Ivy style canon. A sack suit, for the unfamiliar, is an easy-fitting type of suit that came into prominence in post-war America and especially on college campuses in the ‘60s. It’s characterized by a few important features: unpadded shoulders, an undarted front (meaning it doesn’t have that vertical line on each side), an unsuppressed waist, a single center vent in the back of the jacket, and, I’d argue most importantly, what is known as a 3/2 or three-roll-two closure, where the opening of the top button (which you’d never button) is exposed on the rolled over lapel, like so.

J.Press Suit — J.Press is another iconic maker of sack suiting.

J.Press

Eventually, the sack suit fell out of favor, and American suiting began to feature more structured shoulders and pinched waistlines for an all-around more streamlined look. The looser-fitting suits of the past were left behind by everyone but the most conservative of dressers, most notably conservative politicians. George H.W. Bush, for instance, has come to be known as an icon of the style.

So for me, as a then-32-year-old dude who made a living writing about indie rock, there was something lightly subversive about adopting the style. Ironic, even, if we’re being honest. The key, of course, to dressing this way is to carry yourself, or to accessorize in a way, or to get your tailoring just right so that the implied subversiveness isn’t lost and you wind up just looking like…George H.W. Bush. And as a now-45-year-old father of two, albeit with far more tattoos than I had at 32, I do worry that I can’t quite pull it off. That the other dads at school pickup or whatever wouldn’t immediately be like, “Ooh, I get it, he’s a creative type who’s reclaiming traditional American style from the stodgy masses!”

Unsurprisingly, the Brooks Brothers version is a pitch-perfect recreation of the original sack suit design. Real menswear nerds will argue that the quality isn’t what it once was, but the features, anyway, are all correct. I, however, currently have my eye on the Kenmare Relaxed-Fit Suit from J.Crew, which, yes, I know is a step down in quality, and, yes, I know it’s double- rather than single-vented. But I’m impressed by the details they do get right — the 3/2 closure, the generally straight-hanging fit, the patch pockets — and I’m especially drawn to the brown color, which I think reads a bit more college professor than former U.S. president.

Paired with a good blue OCBD, the aforementioned rep tie and those Alden longwings I still can’t quite afford, perhaps my hyper-critical co-worker will approve of my attire at our holiday party this year.