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What to Wear to a Holiday Party Now: A Modern, Smart Casual Style Steeped in the Fits of Classic Menswear

gossipstodayBy gossipstodayDecember 18, 2024No Comments5 Mins Read
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What To Wear To A Holiday Party Now: A Modern,
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When you don’t want an ugly Christmas sweater OR a velvet tux.

For decades, what we now refer to as “classic menswear” was the standard—the surefire way to look polished, confident, and put together. Then the pendulum swung, and everything became slimmer and more casual. What often gets lost, though, is that classic menswear traditionally embraced fuller cuts—suits and trousers designed for both comfort and clean drape. In the process, guys began to associate tailored clothing with stiffness or outdated formality.

Some guys hear that fit has loosened and they immediately reject anything similar to the ultra baggy styles we wore in high school. But in actuality, it’s an advantage: we can now pull details from these classic menswear eras.

This outfit shows exactly how it’s done: timeless, functional, and modern in all the right ways.

While some folks throw end of year bashes that call for being suited up with green velvet blazers, most holiday parties today are rarely formal, but showing up in our normal style seems insufficient for the end-of-year feeling.

This outfit answers that middle ground with precision. The coat is sharp, the sweater is soft, and the trousers add subtle sophistication. It’s menswear that feels classic without being stuck in the past. You’re dressed, you’re comfortable, and you’re ready to toast the night—no fuss and no costume, just a sharp, modern take on holiday party style.

The Fit That Does the Heavy Lifting

Fit has always been the linchpin of great style. Classic menswear often prioritized fuller cuts that allowed fabrics to drape naturally, striking a balance between comfort and form—a principle that’s returning in today’s silhouettes. The proportions here are what make this outfit work. A long, structured coat paired with fuller cut trousers and a thoughtfully detailed sweater nails the balance. Each piece has room to move while staying intentional, creating a silhouette that feels confident, natural, classic and modern.

The Topcoat: Why It’s the Star Player

men's gray topcoat over beige sweater
(similar): Cole Haan / J.Crew Factory / Dockers / J.Crew

The dark topcoat is the backbone of the look. Historically, a topcoat was a staple for staying warm in cold weather when suits were the everyday uniform. Today, it’s a surprisingly versatile option that elevates almost anything you wear underneath from dress clothes, yes, but t-shirts, denim jackets, flannel shirts, and many others.

This coat bridges formal and casual seamlessly—it works as well over a sweater and trousers as it does over a suit. Its construction is key: broad lapels lend balance and structure to the shoulders, while the relaxed tailoring gives it an ease that feels natural, not stiff. For anyone stuck between a nautical pea coat or an overly technical puffer, this is the refined middle ground.

The Sweater: A Modern Nod to Vintage Workwear

banana republic herringbone french terry sweater sweatshirt
Banana Republic, $60 / Similar: J.Crew, Mack Weldon, Grayers, Flint & Tinder

This sweater plays a quiet but essential role in the outfit. Its simple design—a crewneck with a fuller cut—borrows elements from vintage sweatshirts, pieces originally built for comfort and utility. But here, those details are elevated. The herringbone texture gives it depth, while the cream color adds a soft, refined note to an otherwise dark palette. The fuller shape ensures it layers comfortably under the coat without clinging.

What sets this sweater apart is its balance. It’s relaxed without looking sloppy, thoughtful without buttoning-up. It’s what you wear when you want to look at ease but still considered.

Pleats: What You Need to Know

Pleats went out of style—hard. For years, they were shorthand for bad 90s khakis: baggy, shapeless, and altogether uninspired. But as fuller cuts return to menswear, pleats are following right alongside them due to their function. When trousers have more room through the leg, that extra fabric has to taper into the waist somehow. Pleats help manage the material, creating structure and ease while mitigating bulk. They’re not a trend gimmick, they’re a practical solution rooted in tailoring tradition.

For a guy who’s spent 25 years hearing that pleats are a relic, this shift might take some getting used to. But these aren’t the overdone pleats of the past of the late 80s. They’re sharp, shallow, and intentional—just enough to let the pants drape naturally while maintaining a clean, tailored look up top. Pair that with a high waist, and the result is balance: trousers that sit comfortably without squeezing and flow into a cuffed hem that adds weight and finish. It’s proportion at its best.

The Palette: Understated and Sharp

men's holiday outfit with beige sweater and gray pants

Charcoal, dark marled gray, and cream is a masterclass in simplicity. These are neutral tones that work for everyone, but the key here is how they’re combined. The cream sweater breaks up the dark coat and trousers, brightening the look without straying into festive overload.

This palette works because it’s minimal without being boring. There’s balance—the coat grounds everything, the trousers add texture, and the sweater design detail while keeping things light. It’s the kind of combination that’s confident and clean, where every piece feels considered but not precious. It’s an evening holiday party look without a hint of glitter, velvet, or plaid in sight.

Casual classic Fits Holiday Menswear Modern Party smart Steeped Style Wear
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