How to Dress for the Holidays Like a Cool Girl - Cupcakes & Cashmere

How to Dress for the Holidays Like a Cool Girl

5 tips for looking your best this season.
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If anyone knows how to dress for a cocktail party, it's Anita Patrickson. On any given day, she's styling two to three girls for a red carpet, dressing Chanel Iman for a magazine cover, or fitting Emma Watson for an Oscar gown—and that's when she isn't going to a party herself. As a former fashion editor for Allure (which is where we met, at Condé Nast just over ten years ago!), she constantly inspired me to up my own after-work game, with glamorous accessories and riskier pieces that always paid off. When I sat down with her recently, she said, "Fashion is really an opportunity to showcase yourself the way you want people to see you, and if you have the opportunity to make a great impression, why not take it?" Here are some of her top tips for dressing for holiday parties:

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"It isn't just about being 'fashion-forward," Anita said, "It's about being your version of 'fashion forward.'" Which sounds like a less cheesy version of "be yourself," and exactly the kind of fashion advice I can get behind. "A black dress is great and you can wear it a million ways," she said, "but I'm not a little dress girl. I love a suit, which I throw on with a cute lace bra, some slides, and head out the door." Cocktail attire isn't as one-dimensional as it used to be—take advantage of that and wear whatever you feel best in, whether that's a jumpsuit, LBD, or suit! 

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"If you aren't having fun and pushing the envelope, then what's the point?" Anita said, "If you make a mistake, it means you're doing everything right, quite frankly." Don't play it safe just because you're nervous something won't work—holiday parties are fun, and your outfit can be too! "I guarantee, if one person doesn't like it, someone else will absolutely love it. I like to tell my clients that if you're the best-dressed in Vogue, you're going to be the worst-dressed in People." Lesson learned: Go for the velvet suit, bright-red dress, or tulle ball skirt

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"The one thing I tell clients is to have always something fabulous, that you know looks good, ready to go and steamed in your closet for when you get invited last-minute," Anita said, "We all have those days where we're not feeling great and are in a rush—this way, I know exactly what I'm going to put on so that I can just put on my makeup and leave, without working myself into a tizzy."

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When in doubt, opt for a velvet or metallic option in a beautiful green, pink, or silver with a black shoe. "Metallics are just so sassy and gorgeous and feel very festive—go big or go home and wear an entire metallic outfit," Anita said, "and velvets just feel really luxe, especially if you go with a burgundy or black color and wear a really fabulous pair of earrings." 

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"If you’re going to show a lot of skin," Anita said, "Make sure the dress isn’t tight and thin—or, do something really sexy and skin-tight, but with long arms and a high neckline to balance it all out."

P.S., Looking for more styling tips from Anita? Check out her favorite things, common fashion mistakes, and what really goes into styling for an award show.