Yesterday, I visited the relatively new men's shop Winn Perry for the first time. Owner Jordan Sayler has assembled a fine collection of Cary Grant worthy clothes, which at first glance seem a little intimidating.
I shy away from suits, wing tips, and pocket squares for two reasons: I don't want to look like I'm wearing a costume and I hate being uncomfortable.
Luckily, Sayler has a bunch of tips for dressing elegantly, yet looking modern, and most importantly, keeping it all comfortable!
His 5 tips after the jump.

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Jordan Sayler

1. Get a heavy knit sweater. "It's accessible," says Sayler. "Put-together, but casual at the same time. People in Portland aren't going to be wearing suits all the time."
Consider investing in one that will last, like this hand-knit S.N.S Herning cardigan at Winn Perry
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2. Wear a tie. I know! I thought ties were the most uncomfortable accessory imaginable. Not so, says Sayler. He suggests wearing the tie slightly loose (think Paul Newman playing pool in The Hustler), top button undone or buttoned. I love the way it looks, not stuffy at all. Can't believe I didn't think of it.
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3. Stick to a palette. Sayler suggests stocking your closet with four or five colors that you love. "It takes me five minutes to get ready in the morning," he says. "Everything I own goes together." Brilliant! Spend your time shopping, making sure what you're buying will work with everything else you own.

4. Don't be afraid of accessories. Winn Perry is full of all sorts of out-of-the-ordinary accoutrements. Suspenders, a pocket square or a fine pair of leather gloves can transform an ordinary look into something special and add a pop of color. Sayler cautions about overdoing it, though: "There should only be seven points of interest on a man. Anything more will draw attention away from what should be the focal point--the face."
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5. Fit is everything. Whether you're wearing a suit or a pair of corduroys, your garment shouldn't be so tight that it looks super-trendy, or so loose that it looks sloppy. There aren't any hard rules about fit anymore (take a look at what Thom Browne is doing), the key is finding the fit that works for your body and style. This doesn't mean you have to get everything custom made, however. "Don't be afraid of alterations," Sayler says. "Just taking something in by two inches can make a big difference."
The best in town? Lady Ariel Arrow of Duchess.