Depending on how you look at it, the shift toward winter is either a punishment padded with heavy coats or sweet permission to dive into a pile of oversized knits. But either way, the holidays are a particular, high-pressure microcosm apart from the rest of the season. With them comes a unique set of dressing situations you likely don’t face any other time of year. To help untangle some of these style dilemmas, we put out a call through the Cut’s Instagram Stories for the most challenging, occasion-based queries on readers’ minds. Below, Fashion Partnerships Editor Indya Brown answers a few of the questions we received most frequently, via looks featuring the best of THE OUTNET. Scroll on to find out how to: impress everyone back home when you slide into town (without coming off as obnoxious), avoid cheesy holiday-style traps, and more.
The Less-Obvious Party Look
People really underestimate the versatility of a power suit. It’s unexpected yet sophisticated, and contradicts the notion that holiday-party dressing automatically translates into a dress. When choosing the right suit, consider the silhouette: Oversized and double-breasted feels dressier and less corporate. You want a “party” suit, not something you’d just wear to the office. To add more festive flair, pair it with a bold tennis necklace and colorful heels. This cherry-red satin pair livens up classic plaid and makes the look more evening-formal.
1) Equipment + Tabitha Simmons Hyperion Prince of Wales checked voile wide-leg pants, $219; 2) Equipment + Tabitha Simmons Hamish oversized Prince of Wales checked voile blazer, $312; 3) Casadei Gathered satin sandals, $315; 4) CZ By Kenneth Jay Lane Rhodium-plated crystal necklace, $383
The In-From-the-City Outfit
The upside of being around family and old friends during the holidays is that there’s usually less of an obligation to look ultra-polished. Of course, you probably still want to look your best. My advice: Avoid anything too fussy. You want to spend your time enjoying your company, not making sure you’re perfectly styled every minute — even if you do want your look to wink that you’re doing well. A fail-safe solution is to wear some fancy-looking pants that are also comfy. These loose, silky red trousers are basically glorified pajamas. Add a simple red sweater to create an on-trend monochromatic look. And to hang out with family or for a casual reunion with friends, a cool pair of boots lends some structure to soft separates.
1) Goen.J Quilted shell-trimmed faux fur coat, $424; 2) Nanushka Marie belted satin wide-leg pants, $258; 3) Iris & Ink Lucrezia 18-karat white gold-plated sterling silver faux pearl cuff, $175; 4) Iris & Ink Leather ankle boots, $190; 5) N.Peal Cashmere sweater, $325
The Balmy Celebrations Ensemble
I actually find it more fun to get dressed up during warmer weather — you don’t have to worry about a coat! But it does present a conundrum for the holidays: How do you look temperature-appropriate, and be comfortable, without looking like you’re on a tropical vacation (assuming you’re not on one)? Lean on colors and textures associated with winter — reds, deep jewel tones, metallic colors, and sequins — along with breathable fabrics and shapes. A shorter, ruffled burgundy dress hits the right seasonal notes, but in lightweight silk jacquard. And if the heat in your hometown (or wherever you’re visiting) means velvet or faux fur is too stifling to wear, work it in with accessories. You can easily add on even more holiday glamour with crystal embellishments, seen here on earrings and skin-baring heels.
1) Bounkit 14-karat gold-plated quartz hoop earrings, $162; 2) Tara Zadeh Crushed-velvet clutch, $289; 3) Stuart Weitzman Embellished cutout leather sandals, $305; 4) Zimmerman Cascade silk-jacquard mini wrap dress, $375
The Fresh-Luxe Formal Look
I’m a big fan of a classic wrap dress — you really can’t go wrong with one. If it’s midi or above-the-knee length (who says you have to wear floor-length for a formal occasion?), opt for a pair of sleek over-the-knee boots instead of wearing tights. These ones are like calf-hair stockings that wrap cozily around your legs. There are so many textures to play around with during the winter; it’s okay to explore! The varying iterations of softness provided by a fuzzy coat, animal-hair boots, and a velvet dress juxtapose nicely together for heightened depth. To contrast a deep color palette, choose an accessory or two that shines bright, like these elegant crystal drop earrings.
1) Ganni Bouclé wool-blend coat, $198; 2) Oscar de la Renta Gold-tone crystal clip earrings, $312; 3) Michelle Mason Velvet wrap dress, $350; 4) Oscar de la Renta Frederikke lace-up calf-hair thigh boots, $988
All images courtesy of The Outnet.
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