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Dining outdoors is evolving our winter style. Here's how to keep stylish and warm. 

Cassidy Litvack, 31, of Manhasset, Meg Gitlin, 34,

Cassidy Litvack, 31, of Manhasset, Meg Gitlin, 34, of Roslyn, Lisa Hayim, 32, of Port Washington and Jaclyn York, 31, of Muttontown, dine outdoors in cozy style at Trattoria Diane in Roslyn on Nov. 6. Credit: Bruce Gilbert

"Cheers!," exclaims a 30-something quartet of women in unison as they barely clink glasses during a recent outdoor "girl’s night out" dinner at Diane’s Trattoria in Roslyn on a very cool night. They are among the cautious customers who value the social aspects of going to a restaurant but have opted to continue al fresco dining despite the cold, because they consider it safe.

But while they’ve given up the of ease of indoor dining until further notice, fashion, along with comfort and warmth, is still playing a starring role.

"Heat lamps are a help but they only make it tolerable. You need more," says Cassidy Litvack, 31, a psychotherapist from Manhasset. Litvack feels safer dining outdoors. She relishes this bimonthly night out with friends, and she’s definitely not ready to sacrifice style for it. "You want to wear something that’s warm but not too bulky," she says. "You want to wear fashionable outerwear that is functional and still looks cute, and you can do it," she says wearing a cozy, plaid wool coat and a knit metallic headband.

It seems like eons ago when dressing for dining out used to be a fairly simple affair — cute top, cool shoes or boots, a saucy dress or perhaps a favorite pair of jeans. But now, with temperatures dropping, well, it takes a little planning. That coat that you once checked or flung over a chair becomes a major player and may stay for the entire dinner.

Adam Glassman, creative director of "O, The Oprah Magazine," echoes Litvack’s sentiments. "You don’t want to be in a giant puffer coat trussed up at a table and looking like the Michelin Man." But not to worry, he says. "We’re lucky because it’s a fabulous coat season."

Litvack’s friends and dining companions have gotten the memo. Lisa Hayim, 34, a registered dietitian and wellness counselor from Port Washington turned out in a sweater-topped dress layered over jeans, a star-printed faux-fur swing coat and pale knee-high leather boots with a heel for the night. "It defeats the purpose of going out to sit there shivering," she says. "Pre-COVID I was a lot more casual but now I give it a little more effort."

As the temperature drops further, she expects her wardrobe adds to include an extra layer of socks and "hand and foot warmers that we typically take skiing."

Fashion stylist Melanie Lippman of Remsenberg says her clients, mostly female attorneys, are clamoring for fashion pieces that work outside and way beyond the courtroom, including for dining out. "It doesn’t really matter what you’re wearing on top anymore. It’s all about the jacket or coat," she says adding that her clients "are looking for accessories to coordinate with their jackets like hats, fingerless gloves and scarves.

At Diane’s Trattoria, Jaclyn York, 31, a public relations executive who lives in Roslyn Harbor says, "There’s a new strategy. I’ve added over-the-knee boots to wear on top of skinny jeans and I layer a tank top, sweater and jacket over it." This night, she dons a furry, fingerless pair of gloves. "They’re just so cozy and warm, and you still have your fingers to eat."

Hot tips for dining out in cold weather

If there’s one overarching piece of advice for dressing up for dining outside in cold weather, Adam Glassman, creative director of “O, The Oprah Magazine,” summarizes: “Layering is key. And you want to dress kind of like you’re going snowshoeing or skiing in the spring.” Here’s some advice from Glassman and other experts:

— It’s all about that base: “Live in layers,” says Alexandra Karcev of Farmingdale, who is the marketing director of layering brand Cuddl Duds. “A good layering wardrobe will never let you down. There are sensible, smart pieces made to be combined with each other and mixed with other items in your closet to make any outfit temperature-friendly.” If you only buy a few pieces Karcev recommends a stretch thermal, “because you can wear it alone or wear it over something.”

— Leg liners: Line your feet and legs advises, well, everybody. Glassman says, “Start with slim long johns and keep in mind long socks and tights.” Stylist Melanie Lippman of Remsenberg is a fan of the season’s leather and faux-leather pant trend as a wind blocker, while Karcev says that thermal leggings are “super soft and keep you warm.”

— Boot camp: “It’s a great boot season,” says Glassman. “Look for something that will keep your feet warm somewhere between a hiking boot and a fashion boot.” Lippman agrees and suggests paying attention to materials. "Choose boots that are lined rather than just fashionable boots. Consider thicker and waterproof materials."

— Move it: "When you’re eating, movement is so important," says Lippman who favors the warmth of faux-fur vests. “Puff sleeves are still popular and you can show them if you wear a vest,” she says. She suggests looking for coats with a mixture of materials and embellishment and urges her clients not to shy away from color. "It’s the star of the season.” Glassman says, “There are a lot of sleeveless coats available this season that you can wear over a chunky sweater. Or consider a slightly longer puffer vest. When you’re sitting outdoors think about the length and side slits of what you’re wearing so you’re not sitting on your coat.”

— Scarf it up: Scarves can be your outdoor multitasker, says Glassman. “Go for a big one that can double as a blanket. If you get too warm in your coat you can take it off and toss the scarf over your shoulders.”

— Glove love: “A lot of restaurants are giving out QR codes instead of menus so go for gloves with touch technology,” says Glassman who also likes fingerless styles so you can eat and styles with pop-tops just in case you get cold.

— Hat’s on: “I think at this point we have to give up the notion of not wearing a hat at dinner,” says Glassman. “You lose all the heat through your head so wear knit headbands, ear muffs or a hat that’s lined in a material that doesn't ruin your hair and keeps you from getting static.”

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