How To Repeat Outfits This Holiday Season (& Not Get Caught)

Photo: Courtesy Of Pixie Market.
Don't be a serial outfit-repeater this holiday season. While establishing a signature look that consists of a few pieces you can wear over and over again has its merits, there's a fine line between rocking a personal style uniform and straight up wearing the same exact item of clothing every single day.

But alas, as holiday party season approaches each year, we always seem to feel like our closets just don’t cut it — and neither will wearing the same dress to every celebratory event and friend-group gift exchange. To face this wardrobe-challenging time with grace, you’ve got to know how to make a few staple pieces feel totally different for every occasion that presents itself from now until the New Year. Outfit repeating is all but mandatory this time of year, but you've still got to do it right.

So, we’re arming you with the sneakiest, easiest ways to make three core pieces work for three different scenarios — without anyone even pausing to question whether they’ve seen you in that look already. Believe it or not, with staples like a little red frock, cute chunky sweater, and pair of wide-leg jeans, you can tackle nine ho-ho-holiday fêtes and look damn good at every single one. Keep reading to see how.
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1 of 9
The Core Item: Red Dress
The Scenario: Office Holiday Party

You've been waiting for this night all year long, but that doesn't mean you should go straight for the sequins. A bold red minidress with a ruffle neckline is both on-trend and festive-meets-professional. Make it your own with playful accessories like a candy-colored clutch, and let the socks do the glittering. Simple as that.

Pixie Market Red Shift Babydoll Dress, $102, available at Pixie Market. Aldo Newhaven Heel, $69.99, available at Aldo. Mayra Fedane Milo Cloudy Pink Clutch With Studs, $631, available at Runway2Street. Topshop Glitter Lace Ankle Socks $6, available at Topshop. & Other Stories Ball Drop Back Earrings, $25, available at & Other Stories.
2 of 9
The Core Item: Red Dress
The Scenario: Secret Santa With Friends

To make the same dress you wore to your holiday party work for a more casual affair, wear it as a top over some cropped-flare trousers. It's a totally different look that's still festive, but also a little bit more edgy and unexpected. Then, swap the heels for a funky embellished brogue, and your everyday cross-body bag instead of a clutch this time around. Fortunately, this is a totally different friend-group than your work crew, so with this changed up look, they'll have no idea you wore that red number already (despite all the photo booth evidence).

Pixie Market Red Shift Babydoll Dress, $102, available at Pixie Market. Toga Embellished Leather Brogues, $339, available at Net-A-Porter. Mackage Pebbled Leather Crossbody Bag, $320, available at Nordstrom. & Other Stories Ball Drop Back Earrings, $25, available at & Other Stories.
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3 of 9
The Core Item: Red Dress
The Scenario: Outdoor Holiday Festivities

Your whole fam's visiting you this year, and it's time for a tree-lighting and tour around town. How to look good for family photos without buying a new dress? Throw a statement coat over — you guessed it — the same red dress. This way, just the cute little neck ruffles show under the closed coat, and you have an extra layer of warmth and style (feel free to add in some tights if the weather calls for it).

Pixie Market Red Shift Babydoll Dress, $102, available at Pixie Market. Aldo Newhaven Heel, $69.99, available at Aldo. Mayra Fedane Milo Cloudy Pink Clutch With Studs, $631, available at Runway2Street. & Other Stories Ball Drop Back Earrings, $25, available at & Other Stories. Aritzia Beckledge Coat, $98.99, available at Aritzia.
4 of 9
The Core Item: Wide-Leg Jeans
The Scenario: Office Holiday Party

Jeans probably aren't the first thing you put on your list of necessities for holiday season, but as you know, they're the most versatile bottoms in the game. If you already own a cool wide-leg pair — even better! — it's pretty easy to dress them up. All you need is a ruffled blouse and some statement earrings, and then you can take it even further with some thick heels and a beaded clutch. You'll look just as dressed up as the girl in the bandage dress, but be way more quirky and comfortable.

Wood Wood Gwen Wide Leg Jeans, $217, available at MyTheresa. Zara Roll-Neck Studio Blouse, $69.90, available at Zara. Lanvin Tassle Earrings, $590, available at Farfetch. Clare V. Beaded Clutch, $499, available at Clare V. Gianvito Rossi Gina Suede Platform Sandals, $776, available at Matches Fashion.


5 of 9
The Core Item: Wide-Leg Jeans
The Scenario: Secret Santa With Friends

For a more casual night, it's not rocket science to style a pair of great denim. Throw on a cozy turtleneck and your favorite black bootie and you're good to go. But, you can keep the earring and clutch around to keep things feeling fun and festive — why not, right?

Wood Wood Gwen Wide Leg Jeans, $217, available at MyTheresa. Theory Turtleneck Sweater, $270, available at Net-A-Porter. Lanvin Tassle Earrings, $590, available at Farfetch. Clare V. Beaded Clutch, $499, available at Clare V. AGL Booties With Heels And Shearling, available at AGL.
6 of 9
The Core Item: Wide-Leg Jeans
The Scenario: Outdoor Holiday Festivities

It's great that your neighbor's having a holiday bonfire, but that also means you need yet another outfit. But, have no fear — if you haven't caught on, great cold-weather outerwear makes outfit repeating a whole lot easier. You can wear a floor-length topper over that same turtleneck outfit from the other night's gift-exchange without anyone thinking twice about it — because the whole thing's practically covered up. Boom.

Wood Wood Gwen Wide Leg Jeans, $217, available at MyTheresa. Theory Turtleneck Sweater, $270, available at Net-A-Porter. Clare V. Beaded Clutch, $499, available at Clare V. AGL Booties With Heels And Shearling, available at AGL. Front Row Shop Camel Longline Coat, $224, available at Front Row Shop.
7 of 9
The Core Item: Grandpa Sweater
The Scenario: Office Holiday Party

If your work party is an ugly-sweater one, you know you still have to bring your style game — start with a chunky sweater that's more trendy than ugly, but will still fit in with the theme. Keep it elevated yet festive with a car-wash skirt and metallic bootie, and finish it off with a seasonally appropriate bag with a little added sparkle. Just because it's an ugly sweater party doesn't mean you have to abandon your eye for style for a night.

StyleNanda Striped Sweater, $48, available at StyleNanda. Tibi Car Wash Midi Skirt, $192.50, available at Tibi. & Other Stories Velcro Strap Ankle Boot, $225, available at & Other Stories. Charles & Keith Embellished Clutch, $73, available at Charles & Keith. Ale Bremer Jewelry Diamond Wadjet Ring, $78, available at Local Eclectic.
8 of 9
The Core Item: Grandpa Sweater
The Scenario: Secret Santa With Friends

For a 'tis-the-season dinner or drinks with the girls, just slip into a pair of mom jeans and a flat metallic shoe instead of a high-heeled one. Keep your jewelry simple and keep on toting that glitzy cross-body from the other night. It's an outfit that's equally as comfy as it is cute and in-the-spirit (with or without a Santa hat).

StyleNanda Striped Sweater, $48, available at StyleNanda. Topshop Mom Jeans, $70, available at Topshop. Zara Flat Lace-Up Shoes, $59.90, available at Zara. Charles & Keith Embellished Clutch, $73, available at Charles & Keith. Ale Bremer Jewelry Diamond Wadjet Ring, $78, available at Local Eclectic.
9 of 9
The Core Item: Grandpa Sweater
The Scenario: Outdoor Holiday Festivities

You're not the best ice-skater, but somehow your bestie drags you along with her and her S.O. every year. If you're going to third-wheel it, might as well do it in style by adding a turtleneck under your sweater to change up the look from that Secret Santa gathering (and for warmth reasons). But, not just any turtleneck will do, of course — a studded one is twice as nice.

StyleNanda Striped Sweater, $48, available at StyleNanda. Topshop Mom Jeans, $70, available at Topshop. Zara Flat Lace-Up Shoes, $59.90, available at Zara. Charles & Keith Embellished Clutch, $73, available at Charles & Keith. H&M Studded Turtleneck Top, $49.99, available at H&M.
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