The Casual Office Conundrum

Here’s your road map to life beyond the suit.

Iwas working as an editor at a menswear magazine in the ’90s when “casual Fridays” first entered the parlance, hovered for a bit, and then puttered out. The nuances of what was deemed appropriate office attire, once a very understandable uniform of suit, shirt, and tie, now stymied the mind with options. Why was a sweatshirt just a bit too casual but a similar-looking sweater was just fine? Jacket or no? And what about footwear?

Ah, the paradox of choice. Men in today’s increasingly less formal workplace have so many options. And that should be a great thing, a liberating thing, freeing us from the shackles of the suit with its seemingly limited opportunity for personal expression.

But there’s a reason why uniforms work: They’re easy. They don’t require a lot of thought, and, by design, they’re absolutely functional. Now that the suit in some workplaces is having a bit of a breakup, splitting the jacket from its matched pant and requiring a new skill set to make office-appropriate combinations, we need a little help, a road map to navigate this new territory of separates.

Let’s start with the sport coat.

Solid colors are certainly easy to master and show more personality in richer fabrics with some nice depth and surface interest, such as brushed flannels, textured cashmeres, or pinwale corduroys. Express your personality with a subtle windowpane in a contrasting but complementary color to a small-scale check or plaid. Neapolitan tailors like Kiton and Cesare Attolini are masters of the bolder yet tastefully colorful sport jacket with impeccable construction, while Brioni and Ermenegildo Zegna offer a slightly more subtle approach in exquisite fabrications.

Now what goes underneath? Finegauge, lightweight sweaters add a polished but relaxed look when worn over a shirt with the top button undone. Stick with crew-neck sweaters (V-necks can seem a bit too 19th hole) in a neutral, rich palette. Or add a turtleneck sweater. It’s pure myth that you will overheat while wearing one. In a light merino wool, it looks effortlessly elegant.

For shirts, try solids and checks on pale grounds for our sport jackets, and in colors that reference those present in the sport jacket’s pattern.

And now for those pants. You won’t go wrong with a flat-front straightleg trouser in a simple worsted wool. Charcoal, light gray, and navy pair with just about anything, while black is a bit too funereal. Consider flannel and pinwale corduroy in rich colors such as dark brown and burgundy for fall and, in spring, cotton versions in khaki and stone colors. In my estimation, Incotex is one of the best makers of this perfect pant for pairing with sport coats. Make it easy: Find the model that best suits you, and return to it each season.

And finally, footwear. A loafer in any of its varieties—penny, tassel, plain vamp, suede, pebbled leather—is the

perfect shoe for a more relaxed look in the office. Handmade Italian shoemakers like Bontoni and Stefano Bemer offer beautifully hand-colored and polished tones in shades of brown, as well as grays and deep blues that are particularly elegant, unexpected options. And as for sneakers, keep it simple and only for your most casual looks and occasions. Berluti and Ermenegildo Zegna have developed sophisticated collections that will pair effortlessly with your casual sport jackets. A personal favorite sneaker line, Common Projects, is a bit more sleek and streamlined, offered in a broad range of neutrals in leather and suede. Its classic Achilles Low court-style sneaker in a charcoal gray, the most versatile color in the sneaker world, goes with almost everything. You will look like the master of informal workwear.