There’s a pretty good post about buyer’s remorse over at A Headlong Dive, covering the basic things you should consider whenever you step up to the retail plate. (The short version: fit matters; brands, trends and markdowns don’t.)

It’s important stuff to know, especially in the age of flash commerce, but we can’t help but think it missed a little bit of the magic that can pop up between a stylish guy, a good shop and a well-made item.

Whenever you find yourself in a fitting room, the question is always the same: Will I wear it? Can I pull this off? Is this me? It’s the most basic question in style, a perpetual final exam, and all the blogs are just homework.

When you get it wrong, it’s usually because you’ve misjudged yourself. We’ve all got pieces that rarely make it out of the closet—a certain black-and-white houndstooth McQueen shirt, to choose a not-at-all-personal example—and it’s almost always because we misjudged who we actually are. As it turns out, I’m not that avant garde of a guy. That’s why I don’t wear the shirt too much, and I don’t have too many other pieces that go with it. Now I know.

It’s even harder now that we’re looking at a fair portion of our wardrobe-to-be through computer screens, distracted by a web of discounts and, not infrequently, with a countdown clock to muddy the waters even further.

But that’s no reason to give up. There’s still a certain magic to the well-taken risk, the vaguely outré item that stretches your style just enough. It’s a moment of self-knowledge, a rare and personal thrill you don’t usually feel in the world of commerce. If it doesn’t work out every single time (and it won’t), at least you’ll learn something along the way.

—R.B.

CONTRIBUTORS

  • Russell Brandom