• Intelligencer
  • The Cut
  • Vulture
  • The Strategist
  • Curbed
  • Grub Street
  • Subscribe to the Magazine Give a Gift Subscription Buy Back Issues Current Issue Contents
    Subscribe to New York Magazine
  • Subscribe
  • Profile
    Sign Out
Subscribe Give A Gift
  • Style
  • Self
  • Culture
  • Power
  • Style
  • Fashion
  • Black Beauty Matters
  • Parties & Red Carpet
  • Fashion Shows
  • Cathy Horyn
  • The Cut Shop
  • Self
  • Health & Wellness
  • The State of the Uterus
  • Parenting
  • Advice
  • Sex & Relationships
  • Horoscopes
  • Culture
  • Books
  • Television
  • Movies
  • Music
  • Celebrity
  • Power
  • Politics
  • Work
  • Money
  • Rebecca Traister
  • Latest Stories
  • Video
  • About Us
  • NYMag.com
  • New York Magazine
  • Intelligencer
  • Vulture
  • The Cut
  • The Strategist
  • Grub Street
  • Curbed
  • Share
  • Tweet
  • Pin It
+Comments Leave a Comment
  • Style
  • Fashion
  • Black Beauty Matters
  • Parties & Red Carpet
  • Fashion Shows
  • Cathy Horyn
  • The Cut Shop
  • Self
  • Health & Wellness
  • The State of the Uterus
  • Parenting
  • Advice
  • Sex & Relationships
  • Horoscopes
  • Culture
  • Books
  • Television
  • Movies
  • Music
  • Celebrity
  • Power
  • Politics
  • Work
  • Money
  • Rebecca Traister
  • Latest Stories
  • Video
  • About Us
  • NYMag.com
  • New York Magazine
  • Intelligencer
  • Vulture
  • The Cut
  • The Strategist
  • Grub Street
  • Curbed
Sponsor Story
This is paid content produced for an advertiser by New York Stories. The editorial staff of thecut.com did not play a role in its creation.
Sponsored By The Outnet Sponsored By The Outnet
Nov. 12, 2019

Your Holiday Style Dilemmas, Solved

As told to Katie O'Donnell
Photo: Courtesy of The Outnet
Fashion Partnerships Editor Indya Brown

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.

This is paid content produced for an advertiser by New York Stories. The editorial staff of The Cut did not play a role in its creation.

Tags:

  • sponsor story
  • the outnet
  • fashion
  • the outnet holiday 2019
  • outfit collages
  • More
+Comments Leave a Comment
An Editor Solves the Most Common Holiday Style Dilemmas

Most Viewed Stories

  1. My Mom Has No Friends
  2. Olivia Wilde Didn’t Appreciate Being Served Custody Docs Onstage
  3. Madame Clairevoyant: Horoscopes for the Week of August 8
  4. ‘I’ve Been Overworked for Months and My Manager Won’t Help’
  5. How Jennette McCurdy Survived Child Stardom — and Her Mother
  1. My Mom Has No Friends
  2. How Jennette McCurdy Survived Child Stardom — and Her Mother
  3. My Tinder Decade
  4. ‘I’ve Been Overworked for Months and My Manager Won’t Help’
  5. Olivia Wilde Didn’t Appreciate Being Served Custody Docs Onstage

Best of The Cut

  • An Encyclopedia of Celebrity Beauty Brands
  • My Mom Has No Friends
  • Would You Work in an Amazon Warehouse Just to Get Pregnant?
  • Bad Sex
  • Is This the Abortion Clinic of the Future?
See All

The Latest

accidents 7:30 p.m.
Anne Heche in a Coma, Under DUI Investigation, Following Car Crash According to a representative, she has remained in a coma since shortly after the accident.
style 5:50 p.m.
5 New York City Dance Companies, Brought Together The shows, which continue through Saturday, are free and open to the public.
celebrity 4:28 p.m.
Olivia Wilde Didn’t Appreciate Being Served Custody Docs Onstage In new court docs, she said ex Jason Sudeikis “clearly intended to threaten me.”
power 4:02 p.m.
Did Armie Hammer Really Think Voice Notes Were a Good Idea? In the trailer for House of Hammer, the actor shares a violent sexual fantasy in a voice note played by one of his exes.
recommendations 3:00 p.m.
18 Best Butt Plugs You Can Buy Online According to experts.
okay?? 2:41 p.m.
Oscar Isaac Is Still Struggling to Explain That Red-Carpet PDA Apparently he and Jessica Chastain are … like flatworms?
love and war 2:03 p.m.
Tinder’s Fatphobia Problem The dating app’s hold on the culture began around the same time as the mainstream body-positive movement. So why hasn’t anything changed?
By Kelsey Miller
do i need this? 2:03 p.m.
Do I Need a One-of-a-Kind Piece From Éliou’s New Clothing Line? The collection will pair nicely with the beaded necklaces beloved by Harry Styles.
intimacy coordinators 1:17 p.m.
Amanda Seyfried Reflects on Feeling Pressured Into Nude Scenes “I didn’t want to upset anybody, and I wanted to keep my job.”
??? 12:12 p.m.
Prince William Apparently Has Another Sexy Nickname In addition to the “Prince of Pegging,” of course.
parenthood 12:05 p.m.
Mindy Kaling Does Not Care Who You Think Her Kids’ Father Is Apparently, speculation that it’s B.J. Novak doesn’t bother her.
sobriety 12:00 p.m.
‘Can I Stay Sober Without Counting the Days Since My Last Drink?’ If adding up the days one by one makes you feel bad, rethink the math.
By Ana Marie Cox
life after roe 11:20 a.m.
Mom and Teen Daughter Accused of Illegal Abortion Based on Facebook Messages Police obtained Facebook messages in which they discussed ending the then-17-year-old’s pregnancy with pills.
encounter 10:00 a.m.
Abbi Jacobson Knows the Pressure Is On A League of Their Own, her first big project since Broad City, premieres this Friday.
By Katie Heaney
celebrity Yesterday at 2:29 p.m.
Has Camila Cabello Moved on With a Dating-App Founder? She was recently seen holding hands with Lox Club founder Austin Kevitch.
culture Yesterday at 1:10 p.m.
How Jennette McCurdy Survived Child Stardom — and Her Mother She spoke with the Cut about her memoir, her mother’s abuse, and finding solace in Disneyland.
fashion Yesterday at 12:23 p.m.
Japanese Designer Issey Miyake Has Died at 84 Known for his innovative Pleats Please collections, Miyake was a fashion innovator for five decades.
ask a boss Yesterday at 12:00 p.m.
‘I’ve Been Overworked for Months and My Manager Won’t Help’ You need to be less invested in keeping your office running smoothly.
the bachelorette Yesterday at 11:51 a.m.
So, Who’s Going to Win The Bachelorette(s)’? Mid-season front-runners have emerged.
goat Yesterday at 11:49 a.m.
Serena Williams Announces Her Retirement From Tennis In a Vogue essay, she says she plans to step away from the sport after the U.S. Open wraps next month.
More Stories
  • Style
  • Self
  • Culture
  • Power
  • Newsletters
  • About Us
  • Contact
  • Help
  • We’re Hiring
  • Press
  • Privacy
  • Terms
  • Ad Choices
  • Do Not Sell My Info
  • Accessibility
The Cut is a Vox Media Network. © 2022 Vox Media, LLC. All rights reserved.