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As fall arrives, we’re looking forward to seeing loved ones and raising a glass. Do we want to abandon our dignity and return to public in slouchy, formless leisurewear? No, we do not! We want to reconnect with our adoring public in style.

Formality, which for more than a year has been a stranger, can now be a friend. Even more so if you make it personal. Dressing up can be — and really should be — as expressive as everything else you wear. So how do we do it well and in a way that suits our personality? Well that’s the trick, isn’t it?

Illustration by Hilbrand Bos

1 | Don a Bold Patterned Jacket

If you’ve never worn a houndstooth or herringbone jacket, you might find them visually raucous at first sight. I beg you to reconsider. The first sip of Scotch can be a little fiery, too, then it mellows out. There’s a reason Ralph Lauren and Drake’s make coats like these every season: because they look good every season. If you’re feeling shy, stay away from contrasting colors and instead try a cream and tan Prince of Wales jacket or something with warm grays and greens. The pattern is doing the hard work, so the rest of your ensemble can rest easy. A blue oxford, olive cords and a winning knit tie, and you’re playing your A-game.

2 | Think About Counterpoint

Dressing up is about pleasure, so let’s communicate pleasure. The right amount of contrast can be very powerful. If you have a tastefully understated cashmere sport coat, let’s add a bold crimson silk scarf. Now people will think you’ve been spending your time in an esteemed arts residency polishing your memoir. Maybe some suede shoes that are a little lighter brown than you usually wear, which play very well with everything from denim to corduroy. What about a roll neck sweater in an autumnal yellow or orange? Remember: If it’s worn under a dark sport coat, then it’s not too loud at all. You just look like you have a very interesting art collection.

3 | Embrace the Chalk Stripe

Let’s accept the fact that men look good in well-tailored suits. That shouldn’t be hard to do, because it’s true. Gray flannel is classic and a good place to start. But let’s get a little ambitious and add a soft light gray stripe. In a practical way, this elongates the figure. It shows you’re in the business of embracing the occasion. It doesn’t need too much contrast, which gets you into Al Capone henchman territory. But a midnight blue with an easy light blue chalk stripe is wonderful. I would visit a Sid Mashburn store if you’re near one (or his very good website if you’re not). And if you’re in New York City, try the Armoury or Paul Stuart. You deserve a good suit with a little more distinction than usual.

4 | Follow the Velvet Muse

Imagine you’re at the opera or a rarefied dinner party. You see a man wearing an emerald green velvet dinner jacket. At first you think, Is that allowed?  When you realize it is, you wonder, Can I be the man who wears a velvet jacket out and about? Answer: Yes, sir! When you dress up, you set the terms of engagement, and other men look to you as the benchmark of what’s possible. You raise the stakes in the best way possible. A velvet jacket can be worn with a white dress shirt and a solid tie, even with black jeans (though I would opt for gray flannels). You can usually find one in an appealing ruby tone or even black on Mr Porter. You know this strategy is working when the hostess comes up to you, rubs your arm and says, “Is that velvet? I thought so.”

5 | Consider a New Color

We all get into habits, and they can be perfectly reassuring. But sometimes we need to move a few degrees in a new direction. As in all new ventures, it takes a little getting used to. But after a week of wearing moss green cords or a nutmeg sweater, you won’t believe you ever lived without them. The burgundy family is good, as is its sibling, aubergine. Warmer greens and browns, from almond to chocolate, can expand your palette in a winning way. We feel more alive when we reflect a world full of color. As we reconnect with society, let’s do so with verve and a sense of style.

A Minnesotan turned New Yorker, David Coggins is the author of the New York Times bestseller Men and Style and writes a style column for Artful Living.

Read this article as it appears in the magazine.

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