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What Do You Do When the Party Invite Says ‘Dress to Distress’?

The most wonderful time of the year can also be the most confusing.

What Do You Do When the Party Invite Says ‘Dress to Distress’?

The most wonderful time of the year can also be the most confusing.

relates to What Do You Do When the Party Invite Says ‘Dress to Distress’?

Photo Illustration: 731; Clothing: Vendors; Background: Getty Images

relates to What Do You Do When the Party Invite Says ‘Dress to Distress’?

Photo Illustration: 731; Clothing: Vendors; Background: Getty Images

Dressy Casual. Semi-Fabulous. New York Eleganza. Pimp Chic. Revved Up Rockabilly. Bedazzled Blues.

As if navigating the landmines of office parties wasn’t difficult enough, this season there seems to be an eccentric arms race among hosts for the most outlandish holiday party dress code. (Yes, those missives above are all actual invites we’ve seen.) It’s enough to make you long for the halcyon, casually confusing days of “Dress Festive.”

“There are two types of dress codes: the ones that tell guests how to fit in and the ones that tell them how to stand out,” says the in-demand event planner, Bronson Van Wyck. Even when there’s no dress code noted, but especially when one might demand “Festive Casual Black Tie” (seriously), embracing a bit of eccentricity is all part of the seasonal fun—and it’s easier to execute than one might think.

To start, small accessories can make a big difference, says Van Wyck, just use them judiciously.

relates to What Do You Do When the Party Invite Says ‘Dress to Distress’?
A quality velvet blazer can become a party staple year after year (from left): Tom Ford Burgundy Velvet Atticus Jacket ($4,130), Gucci Palma GG Velvet Jacket ($3,700), Boglioli Charcoal K-Jacket Slim-Fit Velvet Blazer ($1,130)
Source: Vendors

“Swap out your standard dress shoe for a smoking slipper, or add an Alexander McQueen silk scarf to go under your dinner jacket,” he said. If even that feels a bit too risqué, consider subtle tweaks to classic garments. “In a sea of black suits, a deep royal blue or rich charcoal gray becomes immediately memorable,” he says.

Andrew Weitz, a Los Angeles-based stylist and fashion consultant and owner of the Weitz Effect, frames the holiday party as an opportunity to impress friends or co-workers, and implores his clients to approach it differently than you would, say, your day-to-day work attire or even something you’d wear to a non-holiday soiree. He, too, says small changes can yield big benefits.

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Small accessories can make a big difference (from left): Elizabetta Cavallo Silk Neckerchief ($66), Rumisu Silk Aloha Pocket Square ($135), Alexander McQueen Biker Skull Scarf ($260).
Source: Vendors

“You can add a festive-colored pocket square or a pocket square with a print on it,” he advises to those looking to dip a toe into the proverbial shallow end of “holiday” dressing. But for men ready to dive in and make a splash, he has two items that have become standbys for this time of year. “I always suggest a velvet blazer as an option, in a really nice black or some sort of green or a rich red, ruby red.” (If indulging in a bit of velvet, Van Wyck recommends limiting it to one item—a blazer or loafer from a brand like Tom Ford, Saint Laurent, or Gucci.)

Additionally, Weitz says a sweater can be used to add a bit of sophisticated holiday spirit—not to mention it’s cozy. He opts for cashmere or cashmere-blend with a seasonal design, like Fair Isle, or in a classic texture, like cable knit, or an elegant turtleneck. All three are elevated without being too showy, and if they fit well and are worn with confidence, he guarantees people will notice.

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Swapping out a dress shoe for a bold smoking slipper, while keeping the rest of your outfit reserved, is an easy way to stand out (from top): Jimmy Choo Crystal-Embellished Velvet Smoking Slipper ($995), Smythe & Digby Fleur de Lis Embroidered Slippers ($169), Dolce & Gabbana Floral Slippers ($995)
Source:  Vendors

“Wear the sweater with wool pants and a suede boot or shoe,” he says. “All together it will convey warmth and a holiday feel.”

Van Wyck also likes a holiday sweater and notes that it’s a wardrobe staple you can get mileage out of post-holidays. And while he says red and green are great ways to add some festive zest to your outfit, avoid wearing the colors together. “It looks cheesy,” he says.

Both men strongly frown upon what has, in recent years, become a bit of an ironic holiday tradition: the ugly holiday sweater. Unless you’re going to a party where the tacky knitwear is a requirement, it should otherwise be avoided. “It’s not funny, it’s not cute, it’s old, it’s very 1990s,” says Weitz.

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Avoid a tacky “ugly” sweater and opt instead for a bold pattern, like Fair Isle, to get more use out of it into the new year (from left): Burberry Fair Isle Wool Sweater ($890), Brooks Brothers Fair Isle Sweater ($90), Beams Plus Fair Isle Sweater ($259)
Source: Vendors

And if you’re normally nervous about stepping (dressing?) outside your usual comfort zone, use the holidays as an excuse to throw caution to the wind—come Jan. 1 you can blame any fashion foibles on the eggnog.

So this month, perhaps it’s best to take Van Wyck’s guiding principle to heart: “If you’re unsure about what to wear, follow the maxim that it’s always better to be over- than underdressed,” he said. “Effort is attractive, and a lack of it is not.”

Cheers to that.

relates to What Do You Do When the Party Invite Says ‘Dress to Distress’?
Classic textures in with high necks bring a sophisticated spirit to seasonal sweaters (from left): Brunello Cucinelli Cashmere High Neck Sweater ($3,150), Etro Cable Knit Sweater ($710), Camoshita Melange Knitted Rollneck Sweater ($450)
Source: Vendors
relates to What Do You Do When the Party Invite Says ‘Dress to Distress’?
If not velvet, a patterned blazer is also a solid choice (from left): Paul Smith Tartan Blazer ($1,300), Todd Snyder Silk Water Color Jacquard Shawl Collar Dinner Jacket ($798), Suitsupply Havana Purple Jacket ($399)
Source: Vendors