By Even as a stylist, I often get stumped on what to wear. Making my closet feel fresh and exciting takes a lot of unseen effort (read: folders filled with outfit inspiration that I’m constantly turning to), which is exactly what I’m relying on for my revolving door of holiday outfits this season.
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The holiday season is always jam-packed with events that you don’t necessarily plan for. A festive dinner reservation with friends, a last-minute happy hour, your office holiday party—the holiday season requires a whole slew of outfits that are in a genre of their own. Rather than buying carts of new items to carry me through the holidays, I’m opting to rely on my folder of holiday outfits to inspire me to style pieces I already own in brand-new ways.
No matter what events you have penciled in this holiday season, I’ve found an outfit you can recreate to reserve your spot as the best dressed in the room.
10 Holiday Outfits to Wear This Season
1. A Tweed Jacket and Jeans
I’ve never felt the need to add a tweed jacket to my wardrobe until I laid eyes on this impeccable styling. While the jacket itself is quite feminine, styling it with baggy jeans makes it feel cool and understated rather than completely preppy.
Sleeper
Tweed Jacket
Anthropologie
Tweed Jacket
Abercrombie
Mid-Rise Slouchy Jeans
3 colors available
Dolce Vita
Distressed Leather Mid Heels
6 colors available
2. Red on Red
I recently struck up quite a bit of controversy by styling a red cardigan draped over the shoulders of my trench coat, something I often do, so imagine my delight when I saw this outfit as inspiration to double up by doing the same thing over another red sweater. The tone-on-tone layering is begging to be worn this holiday season and can be done with the knitwear that already exists in my closet. Rather than draping it over my shoulders, I’ll be opting to tie my red cardigan diagonally across my body to recreate this look.
NAADAM
Cashmere Sweater
20+ colors available
GAP
CashSoft Cardigan
8 colors available
Levi’s
Baggy Dad Jeans
14 colors available
Madewell
Chunky Cuff Bracelet
3. Sequin Pants
No holiday season is complete without wearing a healthy dose of sequins. My favorite way to style sequins is with juxtaposed pieces, be it a blazer paired with sequin bottoms like the image above or a sequin top paired with everyday jeans. It allows the sparkly details to read as cool rather than too on-the-nose for the holiday season.
Sézane
Chelsea Blazer
6 colors available
I.N.C.
Sequin Pants
2 colors available
Sam Edelman
Slingback Pumps
15+ colors available
J.Crew
Leather Crossbody Bag
2 colors available
4. Bright Layers
Hands down, the best part of cold-weather fashion is the return of layers. What could have just been a polo and jeans here is heightened by the use of color, print, and texture. (Not to mention the killer statement accessories.) While styling bright colors for winter can be intimidating, the double-layered, neutral outerwear helps to ground the warm weather-leaning shade of green, which can be replicated as an unexpected outfit this holiday season.
J.Crew
Cashmere Sweater
15 colors available
Old Navy
Double-Breasted Blazer
2 colors available
Ralph Lauren
Polo Bear Wool Scarf
Anthropologie
Triple Loop Earrings
2 colors available
5. Jeans and a Fur Coat
While this look’s base is a simple crewneck and jeans, what makes it holiday-worthy lies in the details. With the faux-fur trend resurging this season, it’s a better time than ever to add a fur coat to your wardrobe. With an oversized bag and a socks-and-heels combination, the effortless vibe of this outfit is one I’m dying to emulate.
Abercrombie & Fitch
Faux-Fur Coat
3 colors available
Everlane
Cheeky Jeans
8 colors available
Amazon
Suede Tote Bag
2 colors available
Schutz
Slingback Mid Pumps
3 colors available
6. Leopard and Red
I may have worn this outfit just last week, but red and leopard is truly the combination I can’t get enough of this season. With an added pop of silver? Say less.
Free People
Leopard Duster
GAP
Chunky Scarf
8 colors available
J.Crew Factory
Penny Loafers
2 colors available
GAP
Ribbed Gloves
4 colors available
7. A Sheer Skirt
Trust me: You shouldn’t let the words “sheer” and “skirt” scare you. While you could opt for a fully sheer skirt like the above picture, the skirts I personally have my eye on have short slips underneath to provide the sheer effect with a little more coverage. And when paired with a chunky sweater on top? Juxtaposed holiday perfection.
Everlane
Crewneck Sweater
Grey Lab
Sheer Sequin Midi Skirt
Open Edit
Sheer Mesh Midi Skirt
2 colors available
Sam Edelman
Slingback Pumps
3 colors available
8. A Plaid Skirt and Knee-High Boots
Though I’m normally not one to sport a ton of plaid, let alone a plaid skirt, I’ve never saved an image faster than I did this one. Her it-girl accessories—in winter white, might I add—combined with a fur-trimmed vest and knee-high boots give the prairie-girl look a chic new direction.
Free People
Fur Vest
Damson Madder
Checkered Kilt
J.Crew
Stevie Knee-High Boots
2 colors available
Epifene
Marble Resin Bangles
9. Red Socks and Mary Janes
While a maxi dress and trench coat is a simple base on paper, the combination is taken to another level with Mary Janes paired with red socks as a shoe choice. The small detail makes a huge impact and can be used to make virtually any outfit feel holiday-ready.
Banana Republic
Trench Coat
2 colors available
Amazon | CozyWow
Red Tights
20+ colors availalble
Dolce Vita
Patent Leather Heels
2 colors available
Madewell
Mini Shoulder Bag
5 colors available
10. Red Sneakers and Trousers
Although a blazer and trousers pairing is business casual on paper, when paired with a ball cap and sneakers, the duo is totally transformed. Here, the tonal look is made more interesting through different variations of the same shade, a bit of added texture, and a pop of gold. Oh, and need we not forget the standout piece of it all: red sneakers.
Abercrombie & Fitch
Wool-Blend Coat
2 colors available
Aritzia
The Effortless Pants
15 colors available
Adidas
Sambas
Dolce Vita
Crimson Suede Sneakers
12 colors available
