8 Easy & Chic Outfits for The Holidays

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8 Easy & Chic Outfits for The Holidays

The holidays are in full swing – but your schedule may not be as packed with social activities as it usually is. Because the 2020 holiday season is all about being at home and casual evenings. But there’s no reason that you can’t still enjoy dressing up! Because you CAN enjoy your holiday wardrobe, even if your schedule is a bit more low-key this year.

Check out 8 outfits that I created that allow you to still feel as festive as possible, depending on how dressy you want to get. Because yes, you can dress up just because it’s the holidays and just because you’re in a festive mood.


8 Easy & Chic Outfits for The Holidays

So, you have a fancy skirt that you love to wear to cocktail parties – but how can you dress it down a bit? Add a cozy sweater! It’s an unexpected pairing that feels a little more 2020 appropriate, and you still get to wear sequins. I love this combo that keeps it tonal and elevated – just add slip-on heels (and a cute mask!).

WEAR THIS TO: Socially distanced cocktails.


8 Easy & Chic Outfits for The Holidays

Many of my clients love a jumpsuit as a step down from a cocktail dress, since pants are usually a little more casual and a little more comfortable. But a jumpsuit can pose challenges, specifically when going to the bathroom! So, you can get the same look with a matching top and pants. And the benefits are twofold – a top and pants can be a much easier fit than a jumpsuit (especially if you’re a different size on the top and bottom), and it creates a long and lean silhouette with a continuous column of color (read this for more about a column of color). And this year is all about getting maximum benefit with minimum effort.

WEAR THIS TO: Date night – even if it’s on the couch.


8 Easy & Chic Outfits for The Holidays

Ok, I know what you’re thinking. “Paul, why would I wear a cocktail dress this year?” And my answer is, “why not?” Make pulling your outfit together easy-peasy with metallic accessories – because if any year calls for shining brightly, it’s this one. (And click here to read why I’ll always love metallic accessories.)

WEAR THIS TO: A black-tie optional Zoom party – because that’s how you roll.


8 Easy & Chic Outfits for The Holidays

A super simple 2020 holiday outfit (that’s probably sitting in your closet) is an embellished top, comfortable wide leg pants and festive flats. The top does all the work for the outfit, whether you choose lace or sequins or beading – and the pants ensure that you can enjoy a holiday dinner and then flop down on the sofa.

WEAR THIS TO: Your at-home holiday party with your immediate family.


8 Easy & Chic Outfits for The Holidays

Velvet is synonymous with holiday dressing, and nothing is more versatile than a velvet blazer. You can toss it over a cocktail dress just as easily as you can wear it with jeans. A velvet blazer and silky blouse are a natural pairing, and combined with cropped jeans and booties, it’s the perfect outfit for when you want to feel dressed up, but not too much. And if you love a velvet blazer, check out all the ways you can wear it here.

WEAR THIS TO: An outdoor holiday lunch.


8 Easy & Chic Outfits for The Holidays

A sweater dress is a fall and winter staple. Dress it up, dress it down, it can probably take you anywhere – click here to see what I mean (along with a few other versatile holiday styles). Which is why it’s the ideal item when you want to feel cozy but are tired of your jeans & leggings. Just add boots and you’re all set (and if you’re concerned about being cold, wear a long sleeve t-shirt and heavy tights as under layers).

WEAR THIS TO: A day full of dropping off gifts on your family’s and friends’ doorsteps.


8 Easy & Chic Outfits for The Holidays

To beat the chill this season, channel your inner snow bunny with a faux-fur vest! The vest is essentially the ‘star’ of your outfit, so keep the rest of your look simple (if you want to create other outfits with a ‘star’ piece, read this). Pick any shade of neutral faux-fur and throw it over black layers – a slim turtleneck and coated black jeans that look a little like leather. It’s an outfit that’s just as easy as blue jeans and a puffy vest, but with a lot more winter wow.

WEAR THIS TO: Roasting marshmallows on your neighbor’s back porch.


8 Easy & Chic Outfits for The Holidays

When you’re staying at home and you want to elevate your look beyond workout wear, nothing beats a cozy sweater and suede or leather lettings (check out 5 faux leather leggings outfits here). And if you’re heading outdoors, just add boots and your favorite wool coat.

WEAR THIS TO: An evening sitting by the fire.

Do you know someone who deserves to feel better about how they look? Contact me to discuss a Gift of Style – a truly unique gift that they’ll remember forever. I can tailor a Gift of Style to their individual needs (virtual closet audit, shopping & styling), so that they can start loving what they see in the mirror. And if you’re looking for a gift for yourself, check out Style Portfolio – a virtual service that gives you a toolkit to jumpstart your style, so you can start the new year off right.


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