Go Big And Nail That Oversized Shirt Look

I’d been on the hunt for a heritage-quality flannel shirt — one of those sturdy sonsabitches that can practically stand up on their own — when my wife insisted she buy me one. Toasty flannel, in winter? No contest here, but it did mark a certain departure from the more fitted looks I’m used to. (Let’s just say these guys rarely come in slim.) After trying on a few around town, I knew that if I were serious about nailing the look I had envisioned, I’d have to relax and embrace the oversized shirt.

The one detail you have to get right

Although you can safely plan to skip the tailor, you’ll still have to pay attention to fit. Overlong sleeves and a little extra shirttail won’t sink you — in fact, “a little extra” is what this look’s all about — but drooping shoulders look sloppy. (It’s the difference between wearing a shirt and having it wear you.) The shirt’s shoulder seam should hit somewhere on the round of your shoulder.

Tighten it up

A looser top demands more fitted pants. Not only will it emphasize your shirt’s fit by contrast, it gives your outfit more structure and purpose. Denim’s an ideal match, and is readily available in slim and straight fits. Doubling down with more relaxed bottoms is a move that’ll take a lot of swagger to pull off.

Wear it all four seasons

Don’t stow your heavy flannel or denim when the temperature rises. Your heavy, loose shirt works just like a lighter version of its warmer, padded cousin — the classic overshirt or shirt jacket (“shacket”) — and makes for an excellent transitional layer during fall or spring. Roll the sleeves up or down as the unpredictable weather shifts.

Gentleman’s word: My wife bought this Fjallraven shirt from O’s Clothes in Hamilton, Ont. I’d recommend going there because they have racks of sweet, sweet flannel and tough-as-hell heritage brands. We have no relationship.


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