Casual Outfits for Men: 5 Foolproof Outfit Ideas That’ll Make You Want to Dress Up Again

After of two years of wearing gym shorts to work, does “casual outfits for men” still mean anything? If your answer to that question is a half-whimpered “No—please, god, no”, we feel your pain. But if you’re mentally preparing to venture back into the office (or, at least, an office) at some point soon, it’s worth reacquainting yourself with those erstwhile 9 to 5 stalwarts you used to rely on. Turns out, they look kind of different filtered through the prism of a post-quarantine reality. Frankly, they look kind of cool. Which means there might not be a better time to carve out a lane as a bona fide business casual expert. 

Right now, workplaces seem to fall along a spectrum of two extremes: those that still require you to wear a suit, and those that have thrown up their hands, donated their ties, and declared free rein to wear whatever the hell you’d like. If your office falls squarely into the former camp, you have our sympathies. (Here’s a dozen razor-sharp suits to cheer you up.) But if you’re a deeply-relieved member of the latter group, building a rock-solid business casual wardrobe might actually be the most effective way to distinguish yourself from your crushingly swagless co-workers. As it happens, the best of what the genre has to offer comprises a grip of pieces we’ve been singing the praises of forever: unstructured blazers, roomy trousers, wild-style loafers. Which means even if commuting to a cramped cubicle never becomes part of your daily routine again, they’re worth investing in. 

Still not convinced? You’re in luck: Over the last few weeks, we thought deeply about the best casual outfits for men, and condensed the results of our brainstorms into five foolproof looks, each of which you can wear to seal the deal in the the conference room (virtual or otherwise)—and then continue wearing long after you’ve logged off for the day. Here’s where to start. 

The Modern-Day Power Lunch Look

The power lunch used to be a sacred mid-day ritual where the drinks flowed freely and the designer suits were protected from buttery ruin by nothing but a napkin flung across their lap. Today it might mean a sad desk salad or an afternoon dose of caffeine, but it’s still an opportunity to look your best—even if French cuffs are no longer on the menu. An unstructured blazer should already be the centerpiece of your business casual wardrobe, but instead of pairing it with a stuffy dress shirt, opt for a knit polo. You could wear sneakers here, but if there’s any element worth carrying over from the boozy lunches of yesteryear, it’s a snazzy pair of loafers—tasseled or otherwise. 

Engineered Garments “Bedford” jacket

Abercrombie geometric sweater polo

Club Monaco hemp dress trousers

Beckett Siminon “Bernard” tassell loafers

Omega Planet Ocean 600m Co-Axial Master Chronometer

The Logged Off But Not Checked Out Look

Sometimes, inspiration strikes after you’ve already logged off for the day. The same holds true for your outfits. So to really set yourself up for after-hours success, plan ahead accordingly. If you know you’re headed out post-work, do better than simply ditching a tie or shimmying out of a blazer. (Hell, if you’re wearing a tie in 2022, leave the damn thing on!) An A-list suede jacket doesn’t just ooze Old Hollywood style—it shows you’re always thinking long-term, in and out off the office. And when it comes to schlepping your laptop home, ditch the sporty backpack you usually stuff your gym shorts in and reach for a sleek leather bag.

Mr. P “Metis” suede blousson jacket

Orslow US Army fatigue pants

G.H. Bass & Co “Larson” heritage weejun loafers

Shinola vachetta leather weekday briefcase

The New-School Suited Look

In the mood to dress up…sort of? You can still embrace the essence of a suit without wearing any capital-T tailoring. An almost-matching set—like the shacket and trousers combo here—is the perfect opportunity to bust out your dandiest dress shirt (we dig one with a bold candy stripe) provided you distance yourself from the cursed Big Bank™ crowd with some unabashedly wiiide pants. The real trick to ensuring you don’t look like a white collar criminal en route to a court date? Replace those soul-sucking dress shoes with a pristine pair of leather sneakers.

G. Inglese “Lavoro” shirt jacket

Turnbull & Asser candy stripe shirt

Cartier Tank Américaine watch

Jack Purcell low-top leather sneakers

The Mid-Week Blues Look

When you’ve made it through Monday but Friday still feels like a lifetime away, the last thing on your mind is cheffing up a week’s worth of pattern combinations. The simple fix? Ditch ’em entirely and go fully tonal instead. Blue is the classic choice, but regardless of what color you choose, best to avoid wearing the exact same shade head to toe. Keep everything in the same color family—and contrast textures and tones strategically—and no one will mistake you for an extra trying to make himself invisible in the background of a big-budget action flick.

Brunello Cucinelli garment dyed bomber jacket

Portuguese Flannel button-down chambray shirt

Buck Mason Japanese selvedge saddle jeans

Common Projects Track 80 leather-timmed nylon sneakers

Everlane Renew transit backpack

The TGIF Look

Just because the weekend is a few hours away doesn’t mean you should turn up at the office in your binge-watching finest. Sure, you can lean a little heavier into the casual side of the “business-casual” equation by wearing some slyly comfy elastic waist pants—but anchor them with a quality pair of gum-soled chukka boots. A short-sleeve button-up in a summer-y pattern will help remind you it’s about to be the weekend, but a could-be-shirt, could-be-jacket will keep your prying, dress code-minded colleagues on their toes.

Imogene + Willie military shirt jacket

J.Crew short sleeve organic cotton poplin shirt

Warby Parker “Hatcher” sunglasses

Aime Leon Dore linen leisure pants

Drake’s moc toe chukka boots


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