Every once in a while, a reader will email us to ask for advice on how to dress casually (e.g. “What can I wear when sport coats are too formal?”). It’s hard to give direction, unfortunately, since the world of casualwear is so big. Our friend Graeme does well in classic pieces – motorcycle jackets, field coats, chambray shirts, chinos, and denim – but it can also be rewarding to experiment with things off the beaten design path.
For example, take my friend Kyle in NYC (who we’ve featured before). Here he’s wearing a quilted sport coat with some Tyrolean shoes. They’re slightly offbeat items that look odd on their own (indeed, John Oliver lampooned quilted sport coats in his piece on Land’s End), but they can also work well in the right outfit.
“I rarely wear sport coats in a casual context, but I’m a big fan of sport coat styled outerwear,” says Kyle. “This is the kind of thing I grab when I’m wearing denim or faded blue chinos. I usually wear it with crewneck sweaters, turtlenecks, OCBDs, or white tees. The collar is typically worn up, which I find tips it more towards outerwear and away from tailored clothing.”
The shoes are a traditional walker style that comes from the French Alps. Back when Free & Easy was still publishing, you’d often find something like these in their pages somewhere (they even did a collaboration pair with Ando Shoe Company). Kyle admits they look a bit odd in isolation:
“They’re a little overwhelming when you see them close-up in photos, but on foot, everything comes together. They go well with jeans, the kind of jackets you see above, and outfits that have a bit of workwear mixed in. I really like them with the things I’ve been getting from Frank Leder, one of my favorite designers right now. His styles and fabrics lean towards the heavier, ‘sturdier” side of things, and these shoes serve as the perfect visual anchors.”
For better or worse, casualwear has fewer rules. You can always stick to classic pieces such as leather bombers and field jackets, but don’t be afraid to experiment. Sometimes the thing that leaves you scratching you head when it’s on the rack can be your favorite item when worn.