I love the festivity of the holidays—decking the halls, tossing glitter, drinking funny cocktails in antler cups. But there’s one part I dread every year: dressing up. I don’t mean in elf costumes or ugly sweaters. I mean dressing up for cocktail parties, sit-down dinners, and family gatherings (if I show up in jeans, my mother will not-so-subtly ask: “When are you getting ready?”). The thing is, putting on “fancy” clothes is not fun. I find that most sophisticated looks are uncomfortable, time consuming, and usually constructed from sheer fabrics that leave me shivering and miserable. That’s no way to party! It’s not like I lounge in sweats all day, though. My daily uniform consists of cropped or slim jeans, a crisp button-down, and some sort of flats, like oxfords or pointy ballerinas. It’s fine for 9 to 5, but pretty basic after sundown.
Luckily, the fashion community is on my side. With sporty-cool riffs on formalwear from brands like Gucci and Off-White, now seems like the ideal time to up my game and invest in some pieces that are both sleek and easy-going. Could this be the year I find the dressy version of myself, buried under my parka? I decided to consult a few experts to coach me to holiday glory.
“Most people equate dressing up with discomfort, and it becomes an emotional thing,” says Claire Distenfeld, the perennial chic founder of Fivestory boutique in New York City. “But you need to erase that thinking because you can look elevated and comfortable.” She might be onto something. As a kid, I hated dressing up—those tights and scratchy dresses were awful! Perhaps I have negative associations I just need to get over.
“Most people equate dressing up with discomfort, and it becomes an emotional thing. But you need to erase that thinking because you can look elevated and comfortable.”
Distenfeld advises me to think about the go-to pieces I already love, then find their dressier next-of-kin. Since I’m all about jeans with a subtle stretch, she suggests that I try a relaxed-fit suit. “When I worked in the art world, I wore suits all the time,” Distenfeld points out, adding that those from Alexander Wang fit well and look great in grey and navy tones (not black; “a black suit means you didn’t try,” she warns). Allure fashion director Rachael Wang also favors menswear-inspired suits for their posh yet practical attitude. “They’re neat and tidy, and I get them tailored so the hem hits right at the ankle,” she says. “They can be worn with flats, heels, or even sneakers with a tee, a crisp shirt, a silky blouse—or just a lacy bra” (the latter might be a stretch for me, but #goals!). Another option: the tracksuit-meets-tuxedo pants from Valentino and DKNY—pair the suit with a white T-shirt and pumps for a cocktail-ready ensemble.
More holiday style inspirations:
- Can’t Decide What to Wear to Your Next Holiday Party? Try a Puffer Jacket
- Three Top Ballerinas Model Our Favorite Holiday Hair Accessories
- 14 Chic Holiday Party Accessories You Didn’t Know You Needed
But back to my jeans—do I need to give them up entirely? “It depends on the context,” says Los Angeles-based fashion designer Rosetta Getty (i.e. not at my mother’s Christmas party or any champagne affair). Getty prefers wearing a pair of cropped skinny denim with a low heel for a polished touch. In more casual-festive situations, Distenfeld likes pairing jeans with an interesting top. “Blouses are really huge right now, and going forward this is what I’m buying more of,” she says. “Anything in silk will elevate an outfit to be a little more fancy, and I love a bold color, like mustard or orange.” Wang is all about “Victorian high-neck blouses” at the moment, which I can appreciate not only for their feminine charm, but the fact that they don’t reveal too much skin on negative-zero days. Or to go all-out, Wang suggests I “step it up with some gold or sparkly ankle boots,” like those from Brother Vellies or Anine Bing.
Now for those ultra-dressing occasions: Rather than grit my teeth and force myself to wear a barely-there silky frock, Distenfeld says I consider long-sleeve knit dresses that cling to the body but don’t fall into the alarming (for me, anyways) “body-con” category. This dark emerald one from Lemaire checks all the boxes. And since I obviously have childhood issues with tights, Distenfeld says I should pull on tall suede boots to stay cozy. “I have a pair from Stuart Weitzman that hit mid-thigh that I wear with skirts and dresses. On cold days, it’s like having on pants.”
Or I could really wear pants, says Getty. “I like pairing a caftan or dress with trousers as an alternative to a traditional cocktail dress.” Her recent resort collection featured a hammered satin caftan dress paired with straight flare pants in stretch cady. Another statement-making idea: add oversized earrings—it requires almost no effort, but brings a lot of glamour to any outfit. Distenfeld recommends the Rebecca de Ravenel “Bonbon” earrings, which have developed a cult-following and often sell out. “They are by far the easiest way to elevate a look in a milli-second. And they have a little shimmer to them, just like fairy dust.”
No matter the outfit, though, dressing up should be fun. “You want to develop a formula for dressing up that makes you feel like the best version of yourself,” says Getty. “I keep a tight-edit of go-to pieces, so I always have an idea of what will work. Being prepared in that way makes it a lot easier to pull together a look.” And if what you reach for is dressy in your eyes but defies a few dress codes? “It’s good to be unconventional if you’re remaining true to your personal style,” says Getty. (Hear that, mom? I still love you, of course).
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