The Perfect Holiday Outfit

‘Tis the busiest time of year, but how do you get through all this month’s social activity with style and ease? Red Typewriter has got you covered. To inspire your December wardrobe selections, we’ve assembled a few fun and fashionable ensembles for seven different occasions. All of them are guaranteed to increase your holiday spirit and turn heads in your direction.

Occasion #1: Formal Holiday Dinner With His Family: Whether you have a brand new beau or you’re going strong with your partner of 15 years, impress the clan by wearing a classic look with a twist. Pair a skate, swing or box-pleat skirt in a festive hue with a soft black cashmere sweater. Or try one of the season’s must-have looks: a colorful, faux fur sweater (see our Pinterest Page for suggestions.) Accessorize with some pearl jewelry, a ladylike purse and a pair of classic pumps. For added holiday glamour, opt for something in festive gold (see our Pinterest Page, “Golden Child” for inspiration). Below: Burberry fitted cashmere sweater. Tiffany & Co. pearl necklace. Van Cleef & Arpels earrings. Christian Louboutin high-heel Mary Jane pumps.

Occasion #2: Picking Out the Christmas Tree: Heading out to select this year’s Douglas Fir show stopper? Throw together a casual look that radiates hipster chic. Start with skinny jeans and a thermal long-sleeve shirt, then top with a chunky cable-knit sweater, a plaid scarf and knit beanie. Don’t forget the fur-trimmed boots to keep your tootsies warm while you’re tromping through the snow. Below: The North Face green thermal layering T-shirt. Old Navy cable knit sweater. Koolaburra Jovi boots at Revolve Clothing. Asos fisherman beanie. Vivienne Westwood green tartan scarf, currently unavailable. 

Occasion #3: Braving the Holiday Crowds: Hitting the stores this time of year is serious business, so arm yourself with a comfortable yet stylish outfit that helps you navigate the mall with ease. First, ditch the shoes that pinch and opt for comfortable boots that give you great mileage. Next, layer a breathable tank underneath a loose-fitting plaid shirt (find some great options here) and black stretchy leggings. Finish off with some fun accessories and a warm jacket. Let the shopping begin! Below: Plaid shirt at RevolveClothing.com and Splendid white tank. Maurices leggings. Frye Shirley over-the-knee riding boots. Stella McCartney Baby Bella tote at Neimanmarcus.com. Parajumpers jacket. Portolano cashmere gloves in winter blue at Lastcall.com. NYC Upper East Side cuff on Etsy.com.

Occasion #4: The Boss’s Annual Holiday Party: Black may be the safe bet for a business-related event, but don’t be afraid to go for a pop of color. This season, it’s all about jewel tones such as vibrant emerald green. Choose a dress in an elegant but up-to-date silhouette and pair it with strappy metallic high heels and an animal-print bag for a striking ensemble. Add shimmering drop earrings and a faux fur coat in winter white, and you can rest assured all eyes will fall on you the minute you enter the room. Below: Simona Jacquard style dress in emerald at Tibi.com. Marchesa Iris calf-hair box clutch at Net-A-Porter, Joie Jena sandal in bronze, pewter and rose gold at Piperlime. Ericsson Beamon earrings and H&M faux fur coat. 

Occasion #5: Your eccentric friend’s gingerbread bash: Daytime holiday parties call for something breezy and festive. For a fun look, don a pair 0f trendy culottes in a substantial material such as leather or wool, and top with a silky white or off-white blouse. Accessorize with playful vintage accents like a metallic scarf, a crystal pin and a collector’s charm bracelet. Where’s the eggnog? Below: Faux-leather culottes from Asos. BOSS Hugo Boss white blouse, currently unavailable. Gold metallic scarf from The National Gallery. Rhinestone scarf slide at OKA jewelry. Vintage Chanel charm bracelet. Tory Burch Sally 2 black-and-gold leather wedge pump at Neiman Marcus. All Aboard Clock Crossbody Bag by Kate Spade New York. 

Occasion #6: An Intimate Night in Front of the Fire: If the two of you plan to meet under the mistletoe or on the couch to watch a holiday movie, wear something sexy and sweet to snuggle up in. For a look that’s just a little naughty and a whole lot of nice, choose toned-down separates that are soft to the touch and feature subtle holiday accents. You’ll appear cute as a teddy bear in this cozy fleece robe—until he catches a glimpse of the sporty yet seductive ensemble underneath (including panties adored with jingle bells!). Below: White Teddy Robe at Topshop.com. Gray Urban Classics cotton tank on Ebay.com. Jingle Bell cotton panty at Victoriassecret.com. RVCA Moon Shadow thigh-high socks on Amazon.com. 

Occasion #7: Evening Bash: If you’re invited to a New Year’s Eve party or another nighttime event, be bold enough to embrace the season’s sultriest hue: deep red. Dare to wear a stunning mini dress adorned with trendy fringe and pair it with strappy high-heel sandals in a similar shade. Glamorous Art Deco jewelry and a metallic clutch pump up the wow factor and inspire you to dance the night away. Below: Stella McCartney fringed stretch-cady mini dressdress and Saint Laurent high-heel sandals, both at Net-a-porter.com. Mary Francis clutch, currently unavailable.

Photo collages by Inga Lim.

Additional styling and market editing by Maryann LoRusso.