How To Dress For The Party Season

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How To Dress For The Party Season

Words by Derek Guy | Photography by Rory van Millingen | Styling by Kit Swann

2 December 2025

For the incorrigible introverts among us, Larry David is both our comedic relief and voice. A few years ago, he penned something for Air Mail, unabashedly declaring, as he always does, those curmudgeonly sentiments that we dare not say. “I’m a creature of habit,” he acknowledged, “and can’t tolerate anything that throws me off my normal routine. That’s why I detest all holidays, but none as much as Christmas.”

Among the many things David loathes about the holidays, he lists the ever-ringing music, the faux bonhomie and those “movies with their ridiculous, treacly sentiments”. Most of all, he adds, he resents the nonstop social gatherings. Few of us are so obdurate and misanthropic that we’re not willing to perform a bit of geniality. Even if the wind up to the holidays can be a bit stressful, most of us enjoy the company of friends and family (at least some of them).

The challenge, really, is getting through the next month or so. Between shopping for presents, meeting end-of-year work deadlines and the inevitable winter travel delays, social commitments can feel more like a burden than bliss. Plus, you have to figure out what to wear for these gatherings. What’s appropriate for the office party? How does one do “black tie”? And what exactly does “cocktail attire” mean? Rest assured – we’re here to guide you through the finer points of festive dressing with ease and clarity.

01. The office party

Trading hard written dress codes for softly coded norms has made knowing what to wear to work more confusing than ever. Deciphering how to dress appropriately often means observing the cues in your office. Holiday parties, however, present a unique challenge. They’re annual and rare, making it harder to know where the line falls. A simple rule of thumb: aim for something presentable yet relaxed. It’s a party, after all.

For those in formal workplaces where suits are the norm, consider softening your look with an unstructured blazer in an earthy shade of Italian corduroy paired with a dark cashmere rollneck. Alternatively, a navy sport coat, which you can pair with a white spread-collar shirt, tan cotton trousers and leather shoes just a step below Oxfords in terms of formality, such as Derby shoes, chukkas or loafers. Before going to the party, tuck a tie into your pocket as a backup in case the atmosphere calls for a little extra polish. The navy sport coat or corduroy blazer keeps things a touch more relaxed than a full suit while still looking professional and party ready.

If your office leans casual – think T-shirts and jeans – use the holiday party as an opportunity to dial it up. Try a textured sweater, such as a chunky Aran knit from Inis Meáin, with five-pocket cords and leather boots. Combining textures – such as ribbed corduroy, soft suede and the distinctive patterns of fisherman knits – elevates the outfit while staying true to a casual spirit.

02. Hosting a holiday party at home

If it’s your party, you have every right to dress as you please. But if you’re aiming for that perfect middle ground – polished, but making your guests feel at ease – consider dressing down your black tie by combining classics like a shawl-collar tuxedo jacket in a bold shade of white or ecru with a louche silk shirt sans bow tie, or a more upscale Americana approach, featuring velvet tailoring alongside classic washed denim, and a formal slipper by Manolo Blahnik. Sunglasses inside: optional.

Alternatively, a chunky shawl-collar cardigan can take the place of a sport coat while still feeling as comfortable as loungewear. The best ones feature hefty collars that drape like doughy rolls. Toss one over a T-shirt or collared shirt, then add jeans, chinos or five-pocket cords. This helps the atmosphere feel relaxed, so your guests feel at home, while also allows you to present the best version of yourself. Or at the very least feel like you’re the kind of person with a leather club chair inside a home library.

For something a little more rugged, check Ralph Lauren’s sub-labels, Polo, RRL and Purple Label. The brands’ design inspiration often borrows from sporting and Southwestern American themes, which makes them a natural pairing with jeans and chambray work shirts.

03. The black-tie event

If you’re fortunate enough to receive a black-tie invitation this holiday season, rejoice. Most of us don’t get many opportunities to wear a black-tie rig nowadays, even though it’s the most elegant and flattering thing a man can wear. In fact, no one will blink an eye if you wear a dinner suit on New Year’s Eve at an upscale restaurant or even a hotel bar should you so wish.

Figuring out black tie can feel like learning a forgotten language, but you can simplify the process by following some easy steps. First, you obviously need a black-tie rig (or tuxedo, in the American parlance). A peak lapel will feel a little more formal, whereas a shawl collar conveys the relaxed spirit of smoking jackets. With his new reign at TOM FORD underway, Haider Ackermann looks set to be the new king of contemporary eveningwear with a bit of attitude, including a standout polka dot double-breasted tux in mulberry silk and satin.

Next, get a traditional tuxedo shirt with a fly front or pleated bib, as well as the studs and cufflinks that you may need to wear with it. Most men will benefit from wearing a cummerbund, as this will cover up the edge of the bib and any shirt fabric that might otherwise peek out from beneath the coat’s buttoning point. Finally, get the right pair of shoes. Black patent leather formal pumps and Oxfords are the most traditional choices, although Belgian loafers and velvet Prince Albert slippers can look charmingly louche if you’re hosting something at home.

For something less traditional, play around with fabrics. A dinner jacket in brown velvet or cream barathea, for example, can be worn with traditional tuxedo trousers while still conveying the kind of sophistication that you want to communicate.

04. Cocktail attire

Historically, the term “cocktail attire” was quite literal, referring to what people wore to get drinks. Cocktail hour was a social ritual primarily involving two types of attendees. One group consisted of professionals unwinding after work, often wearing dark worsted business suits, white dress shirts and conservative silk neckties. The other group was on their way to evening events, such as the opera, and they were dressed in black tie. Consequently, cocktail attire meant the sort of things people naturally wore to work or evening shows, back when tailored clothing was part of people’s regular routines.

In contemporary times, the definition of cocktail attire is still somewhat synonymous with “dressing up”. If you see it on an invitation, try to wear a tailored jacket. Given that cocktail attire is primarily reserved for evening events, opt for colours and materials that exude elegance, like a vintage-inspired velvet blazer from the likes of Dunhill, a formal shirt with a couple of buttons undone, adding in an accessory like a silk bandana or swapping out classic dress shoes for a black leather Chelsea boot.

You’ll never go wrong wearing a dark worsted suit to a cocktail party. To make things look a little more celebratory and less corporate, consider teaming it with a thin cashmere turtleneck. A dark suit without a tie can look like the night sky without stars, but a thin turtleneck allows you to sidestep this issue while still creating the necessary visual interest to lead the viewer’s eye up to your face.

For a glamorous late-night approach, try a statement TOM FORD coat embellished with sequins, or a dark suit in a mohair-mix. Mohair is a stiff, slipper fibre with a natural lustre. When used for tailoring, the garments glimmer, glow and create pockets of light and shadows as you move. They look particularly good at night when under artificial light, such as you’d find in dimly lit restaurants and bars. When teamed with an open-collared, white dress shirt and black suede loafers, you’ll look like a charming social butterfly, even if you secretly harbour a bit of Larry David’s introversion.