I Went Suit Shopping for a Wedding—and Found a Whole New Way to Dress

It was the week of the wedding when the panic began to take hold. It was my only wedding of the season, and I thought I would wear a suit. “I have a suit,” I thought. But then, on top of that thought, another: “When exactly did I last wear it? And when exactly did I buy it?”

Neither of the answers inspired confidence. I believe the answer to the first was “never,” and to the second, “at least 15 years ago.” The last time I'd gone suit shopping, I'd left with a chalk-stripe grey DKNY, purchased at their boutique on West Broadway, which has long since closed. I’d never worn it because I’d always worn the suit I bought before that, a grey Burberry from Century 21 whose baggy pants made me look like a second-round draft pick from Estonia. That one had finally gone into the Goodwill donation bag some time ago, so I was left with an option I only vaguely remembered.

Out on Long Island at my parents’ house, I unzipped its dust bag like a curator carefully unveiling an ancient artifact. The first tag I saw on the jacket—Made in Italy—was promising. Maybe I had good taste! The second, a single letter—L—was not. Because while the concept of a suit sized like a pair of Nike Prestos seems ingenious, the reality, not so much. And as it turned out, I didn’t even have to try on the jacket, seeing as I could have put the pants on without taking my shoes off first. I still couldn’t remember exactly when I’d bought this suit, but I knew when I’d have to buy the next one: Immediately.

I’m usually paralyzed by the sheer number of options available for any given purchase—honestly, as a sneaker guy, when faced with a tough decision I’d usually just buy both pairs. Fortunately, the foreshortened time frame reduced them considerably. I wasn’t going to get a custom suit made on Savile Row, or get fitted for something at Armani or Prada. (Those choices would have also blown up my non-existent budget.) I could hit up a consignment shop and hope to find something that fit perfectly for pennies on the dollar, but that could take weeks. And while shops that specialized in menswear would have plenty of options, I, Suit van Winkle, did not want options. I wanted a suit that fit properly right off the rack, one that looked like I bought it this decade, where the only thing I would have to think about was the color. What I wanted was J.Crew.

Over the years, even as someone who more often than not wore the same pair of LVC jeans and whatever graphic tee I reached for first, I was aware that J. Crew had democratized suiting turning a formal process into something as easy as, well, picking out a t-shirt. Every time I clicked on their “Extra 40 Percent off Sale Styles!” email blasts, I was greeted by a whole slew of Ludlow separates, two-button wool-cotton-linen jackets and matching slim slacks. Ordering wasn’t an option—I’d have to get it right the first time—so on a Wednesday morning I drove out to the Tanger Outlets in Deer Park, home to a J.Crew Factory Store. Was this the best choice? Not necessarily. But it was the one I had.

At 10 a.m. on a weekday, one can have what essentially amounts to a private shopping experience, even at a college-campus sized outlet mall. I tried on two Thompson suits (the Factory Store takedown of the Ludlow), a navy glen plaid and a plain grey, both in lightweight wool, and experienced several revelations. Chief among them the best fit for me was a 40R, when I distinctly remember buying 42L jackets in the past. This, I surmise, was the size I should have been wearing all along. When paired with the matching pants, the only snipping that was required was to cut off the tags. The fit was perfect.

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