outfit inspiration holiday plans

The Holiday Dressing Staples We’re Loving This Season

Dress for the occasion, no matter where your holiday plans take you. In collaboration with Polo Ralph Lauren.

Although we cherish spending time with our loved ones this time of year, the holidays are all about some of our favorite words, like comfort and indulgence. With that comes a considerable dilemma: How do you dress when you need to log adequate face time with pretty much everyone you know, but also want to throw caution to the wind, drink all of the drinks, leave no oyster unturned?

The trick to looking your best no matter the occasion is expert-level mixing of textures and separates for an outfit that feels layered and compelling (and sure to score many a compliment) but still casual enough that you can actually enjoy yourself. And since there’s no one that nails that combination of ease and polish quite like Polo Ralph Lauren, we’re turning to the brand (especially their Prince Street store in Soho) for the cold-weather essentials to see us through the season. Here’s how:

PS. Come shop our Holiday Picks at Polo Ralph Lauren’s Prince Street Store in Soho, get a quick sketch courtesy of Fashion Illustrator Brooke Hagel and enjoy complementary CYO on Men’s and Women’s knit items 12/15, 12/21 and 12/22 from 1 to 5pm.

Meagan Wilson

Associate Creative Director

1. Double-breasted Wool Blazer: A blazer is an easy go-to for looking dressed up and put together when you’re feeling anything but. I love the dressy feel of this crisp white double-breasted number, while the luxe look and feel of wool tweed goes with just about anything.

2. Lambskin Legging: My other wear-everywhere-with-everything piece of choice: a slouchy pair of leather trousers. While it’s the exact opposite vibe of the jacket, the finish still feels luxe.

3. Croc-embossed Tote: Give me all of the embossed croc, all of the time. I love this for toting around holiday party essentials (emergency mints, last-minute bottles of wine) *and* whatever I’ll need to pull myself together the following morning.

Leah Faye Cooper

Editorial Director

1. Shearling Leather Jacket: My general philosophy about winter dressing is that no matter what I wear, it must be topped with a fantastic, warm coat. Living in NYC means that I do a lot of walking, and even on the coldest days, I’m not one to sacrifice style. I’d happily wrap myself up in this stunning suede shearling all season long.

2. Fringe-trim Suede Skirt: Oh how I love holiday party season. Cocktails…revelry…an excuse to wear fringe multiple times a week. I can already see myself twirling to “All I Want for Christmas Is You” in this skirt. See you on the dance floor, friends.

3. Satin Slip Dress: A slip dress may not scream “winter” at first glance, but as someone who wears dresses all year long, I promise, you can make it work. When layered under a chunky sweater and paired with boots, it’s the perfect look for the office. And if you swap the sweater for a blazer, you have a great party look.

Noah Lehava

Director Lifestyle, and Talent

1. Moto Down Jacket: If you expect me to survive the cold, I need to own a down jacket. I love that this one is in a moto silhouette—not common for a winter coat—which makes it cool enough to wear from the office to holiday cocktails.

2. Ribbed Turtleneck Sweater: If a winter wardrobe doesn’t include a cashmere turtleneck sweater, is it even a winter wardrobe? So luxe, so warm, so versatile that I can make it work for pretty much any occasion.

3. Suede Skinny Pant: I’m not the type of person that can wear skirts or dresses in the winter—kudos to those who can, like Leah!—because I get chilled really quick. That’s why my pant rotation needs to be robust with options, like this buttery suede pant. Just throw on a pair of knee-high boots to complete the look.

Jodi Taylor


1. Suede Military Jacket: Leather is a year-round staple for me (yes, that means summertime, too). I think it’s the perfect material to dress up or down, especially if it’s a jacket. Add to that the fact that this particular one is military style, and I’m game to wear it all holiday season long.

2. High-rise Slim Jean: Call me crazy for wearing denim throughout the holidays, but I find jeans to be insanely comfortable (weird, I know). Plus, they’re much warmer than you think and can be worn with practically anything.

3. Plaid Scarf: If there is one thing I am 90 percent of the time, it’s cold. There is a high chance that on the days I choose to wear this scarf (read: every day), it will be around my neck from morning to night. Life’s too short not to be cozy.

Photo: Courtesy of Polo Ralph Lauren
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