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How to Dress Festively for the Holidays

Make gatherings warm and bright with these style guidelines

A group of people gathered for a holiday party, dressed casually in solid colors.

Ariel Skelley/Getty Images

No matter how dramatically fashion changes, the seasonal style annually donned in proximity to holly and mistletoe is neither beholden to industry whims or design trends.

That’s because holiday style is not about being cool. It’s all about being warm and embraceable, and is best achieved by enlisting these key factors: color, comfort, texture, sentiment and shine. Let’s take them one at a time.


My No. 1 holiday rule: Unless it’s set off by a shower of sequins or your weight in diamonds and rubies, avoid showing up for any festivities in head-to-toe black. Black isn’t foolproof — it’s lazy. And it isn’t necessarily slimming. (Clothes that fit are slimming). But it’s almost certainly boring. More importantly, no matter how smart your little black dress (LBD) is or how dashingly urbane you imagine yourself in matching charcoal turtleneck and blazer, when you’re surrounded by a room filled with dozens of people also similarly clad like elegant bank thieves, you’ll pretty much vanish.

Come on. You wouldn’t decorate your tree solely in onyx ornaments. The true hues of the season are glorious jewel tones. Find one — be it a rich burgundy, deep lapis, malachite green or burnished topaz — and claim it is as your signature color for the holiday. You may be surprised to discover that the right jewel tone is actually far more flattering to your skin tone, as well as your hair and eye color, than black — which can flatten complexions starting to exhibit winter pallor.

Women wearing various color dresses: a rich burgundy, deep lapis, malachite green.

Westend61 GmbH/Alamy; Steve Granitz/WireImage; Astrid Stawiarz/Getty Images for Full Beauty Brands

Mindy Kaling (center) with lapis accessories, and others in jewel-tone holiday dresses.


While the weather outside can be frightful, a more likely scenario is that as you go about your holiday drop-ins, drive-bys and parties, you’ll probably travel in vehicles and wind up in places likely to be overheated. Now add in collective body heat, the occasional crackling fireplace and a surfeit of drinks that are mulled or steamed.

Unless you’re planning on caroling across several square miles on foot, it’s best to face the elements in a down or wool coat, scarf and gloves that can be easily removed to reveal an outfit more appropriate for a cozy living room than a ski lift. Choose clothes in a fabric that breathes and flows — merino wool instead three-ply cashmere, combed cotton rather than Shetland, gabardine over flannel. If you know you get toasty quickly, dress in easily removable layers (for example, a cardigan rather than a pullover). Anyone hosting an event other than a formal affair that demands men wear ties deserves coal in their stocking.

Also, parties involve standing still and endlessly shifting body weight. Wear shoes, boots or footwear that won’t generate cursing within three hours. A heavy sweater may produce a few beads of sweat. The wrong shoe can ruin your evening.  


Right now, it’s all about feelings, and shifting our senses into overdrive. So step away from the world of careful gray and clad yourself in fabrics that are fun to touch, stroke and brush against. Now is the time to bring out those plush velvets, wide corduroys, suedes, faux furs, raised plaids, brocades, tweeds and leathers. Subtlety wins few points in December.  


If you own anything that makes you feel closer to a friend or relative, because they made it for or gave it to you, take it out and wear it with your heart on its knitted sleeve — because it will never be more greatly appreciated than now. As for that infamous Christmas sweater you may possess, once when I was InStyle magazine's fashion director at the height of its influence, I tossed off a gently sarcastic swipe about how hokey I found knitwear emblazoned with reindeers and gingerbread houses, suggesting maybe it was time to retire them. Before you could sing “fall on your knees …” the magazine was flooded with an avalanche of not-so-nice mail. I surrender. Wear them. I’ll look the other way.  


This is easy. We all gaze at Christmas trees and holiday windows because they sparkle. Why shouldn’t you? Take out your favorite jewelry, your most glittery earrings, your gold watch, a bright satin tie, a sequin shell, jeweled cuff links, a statement necklace, a blazer or shirt with metallic thread, even old love beads. Decorate yourself. Will you make the cover of Women’s Wear Daily? Gosh, I hope not. But it may get you big hug from someone you love who’s bursting with holiday spirit. Let your wardrobe help make the season bright. You may find the reaction so positive that it’s like you’re always under the mistletoe. Or in a Hallmark movie. And just a reminder: Those movies always have happy endings.

5 tips to guide you through the holidays

With more and more invitations eliminating dress codes and with style now declaring “anything goes,” the result is an uneasy mix of freedom and confusion. Because there is enough stress over the holidays, here’s an unofficial cheat sheet to help guide you.

1. An easy and infallible rule of thumb: You can make a mistake dressing down. You can never make a mistake dressing up. Looking your best always wins. That doesn’t mean that you show up in a gown and tiara to a tree-trimming party. But don’t hesitate to don something you wouldn’t step into for a casual night at home. The nice thing about being slightly overdressed is that you usually get more than your fair share of compliments.  

2. For men, you don’t have to wear a sports jacket. A handsome sweater will do fine, and a slim-cut pair of trousers that aren’t the bottom half of a suit. Jeans are OK as long as they are either a dark-wash denim or a deep color. However, if you feel more confident and pulled together in a jacket, slip into one that you wouldn’t necessarily wear to the office: corduroy, velvet, a thicker tweed or brighter plaid, for example. Even if you more naturally gravitate to a tie, don’t. And open the top two buttons of your shirt.

3. For women, neither a dress nor pants are preferred. Choose what you look best and most comfortable in. If you’re going to an event space, pull out a party dress. If you’re going to someone’s house, opt for a fabric that’s pliant, a color that’s warm and a silhouette that grazes rather than clings.

4. There is no more perplexing invitation than one that says “Festive Attire.” The request is a cop-out — the host is aiming for a posh-looking crowd but is fearful of imposing a formal dress code. Your host should realize that for some, a bright colored T-shirt with a cheeky, wisecracking slogan about the holidays is real festive. The easiest solution is for women to opt for a cocktail dress (don’t go long!), or a sparkly stop and dressy pants, plus jewelry with some drama. For men, go for a dark suit with an open, solid-hued shirt (it doesn’t have to be white) and a slip-on shoe. Never having to wear a tie is always a reason to celebrate.

5. But if the invite does say “Black Tie,” follow the rule. It means that your host is probably going to the trouble to do something out of the ordinary. Then why not look extraordinary? For women, go all out and pick your favorite look. For men, a dark work suit will not cut it. You’re a grown man. You should own a tuxedo or at least a dinner jacket, especially since there are plenty of outlets offering them for nominal pricing. You don’t have to wear a bow tie, however. (I don’t own one.) A dark silk or silver one will do just fine. Think positive. If you look that good, someone may steer you toward the mistletoe.  

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