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Enlightened packing is a sign of a well-edited mind. It shows you have a strong sense of what you actually need and, in contrast, what’s unnecessary, redundant or even frivolous. A well-considered arsenal of clothing is a testament to self-knowledge. Packing well in turn makes you a better dresser because you develop an understanding of what matters and how to wear it. These essentials belong in the thinking man’s duffel, whether you’re headed to London or Los Angeles, Tokyo or Telluride.

An Unstructured Sport Coat

When men ask me where to start their wardrobe, the first thing I tell them is to get a good sport coat. This is probably the most useful thing you’ll own. There are so many great unstructured ones these days that are perfectly balanced between formal and relaxed. This is your sartorial warhorse; you should wear it often and be associated with it. You can go to a tailor and have one made, you can go online to Mr Porter, you can go to Ralph Lauren. They’re not hard to find. But one thing is crucial: It should feel comfortable the first time you wear it. If there’s restriction in the shoulders, it’s not right for you — and no amount of tailoring will solve that.

A Chore Jacket

I find myself wearing a chore jacket or overshirt more and more. This is usually canvas or twill, has a big collar, and buttons up most of the way. I wear it with a knit tie for my preferred sense of relaxed formality. Most importantly, it’s an easy coat to wear worldwide. Drake’s makes my favorites, but there are more and more about, for good reason.

  A Cashmere Sweater 

I don’t care how much it costs; I don’t care where it’s from. You want a sweater that causes intrigue, curiosity, possibly jealousy. This should feel terrific and make you happy every time you touch it. Maybe it’s time to branch out and try a new color. Something almond or in the wheat region? That sounds nice. Maybe plum or, dare I say, aubergine? Now’s the time. You can break the bank at Loro Piana or find something from Italian designer Massimo Alba, who’s legendary for his knits.

Illustration by Hilbrand Bos

A Good Sport Shirt

A sport shirt, in industry parlance, is the slightly more casual cousin to the dress shirt. The latter is made from a fine fabric in white or blue, usually has a stiff collar, and is meant to be worn with a tie. The former, meanwhile, has a softer collar that looks good unbuttoned, often has a more adventuresome color or pattern, and looks great with a sweater or sport coat. When I travel, I like a shirt that doesn’t wrinkle much, so I pack mostly Oxford cloth, poplin and chambray. And remember: A gentleman doesn’t mind washing his own shirt in an emergency and hanging it to dry.

Twill Trousers

These can be cut like jeans but are a bit more formal because they’re not denim. They’re versatile enough to be dressed up with a sport coat or dressed down with a polo shirt. Plus they don’t crease, so they’re ideal for the road. This is a chance to stray from the standard gray or blue. Sid Mashburn makes them in a series of winning colors. Try burgundy if you’re feeling daring or deep olive if you’re more sober-minded.

Unlined Loafers

The loafer is a universal shoe. I’m thinking an unlined one that is broken in from the moment you put it on. Suede is the way to go. I love tobacco, chestnut or any of the warmer browns. A loafer is at home at any nice restaurant, but you can also wear it to play a little backgammon by the pool. You might experiment with the wonderful Sagan loafer from Baudoin & Lange, which is elegant and addictive. Or stick with the old-guard shoemakers: Alden here in America and Edward Green or Crockett & Jones in England.

An All-Season Scarf

A light-colored scarf looks very good wherever you are and whenever you are. It can do the heavy lifting of being expressive when you’re wearing something dark. A scarf allows you to lighten it up while bringing some whimsy and warmth to your dressing. And it couldn’t be easier. Look for something thin and lightweight, as if you’re boarding a plane to Palm Springs. Showing a bit of your personality is always in season. 

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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