• Intelligencer
  • The Cut
  • Vulture
  • The Strategist
  • Curbed
  • Grub Street
  • Subscribe to the Magazine Give a Gift Subscription Buy Back Issues Current Issue Contents New York Shop
    Subscribe to New York Magazine
  • Subscribe
  • Profile
    Sign Out
Subscribe Give A Gift
  • Style
  • Self
  • Culture
  • Power
  • Style
  • Fashion
  • Beauty
  • Parties & Red Carpet
  • Fashion Shows
  • Cathy Horyn
  • The Cut Shop
  • Self
  • Health & Wellness
  • 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
  • Style
  • Fashion
  • Beauty
  • Parties & Red Carpet
  • Fashion Shows
  • Cathy Horyn
  • The Cut Shop
  • Self
  • Health & Wellness
  • 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
Show Leave a Comment
An Editor Solves the Most Common Holiday Style Dilemmas

Most Viewed Stories

  1. The Return of the Marriage Plot
  2. A Bianca Censori Primer
  3. Este Haim Is Letting Her Freak Flag Fly
  4. What Happened to Maya Kowalski
  5. The Pandemic Skip
  1. The Return of the Marriage Plot
  2. What Happened to Maya Kowalski
  3. A Bianca Censori Primer
  4. Why Can’t Our Friendship Survive Your Baby? 
  5. Este Haim Is Letting Her Freak Flag Fly

Best of The Cut

  • The Cost of Straight Hair
  • Dylan Mulvaney’s Girlhood, Interrupted
  • The Real Houselife of Jenna Lyons
  • Fashion’s Talent Problem
  • A Four-Hour Phone Call With Erykah Badu
See All

The Latest

mfw spring 2024 9:08 a.m.
Everybody is a Critic Gucci’s new designer Sabato De Sarno confronts a fashion consensus. But look closely.
always shopping Yesterday at 4:25 p.m.
18 Best Gift Ideas Under $50 That Are Actually Fun On a budget? No problem.
oh? Yesterday at 3:45 p.m.
Sophie Turner and Taylor Swift Went Out for Spaghetti … Twice What do you think they talked about?
mfw spring 2024 Yesterday at 3:35 p.m.
In a Big Shift, Miuccia Prada and Raf Simons Go Glam Plus: a Tom Ford debut.
sure why not Yesterday at 3:09 p.m.
What If Emma Corrin and Rami Malek Kissed … in the Park? Just two thespians enjoying a romantic dog walk.
life after roe Yesterday at 3:05 p.m.
Nebraska Mom Gets Two Years in Prison in Abortion-Pill Case The woman was accused of helping her daughter self-manage an abortion, which in itself is not illegal, and disposing of the remains.
friday sales Yesterday at 2:47 p.m.
21 Things on Sale You’ll Want to Buy: From Ole Henriksen to Outdoor Voices Including extra-strength vitamin-C serum, work-appropriate backpacks, and golf shoes.
zodiac seasons Yesterday at 2:45 p.m.
Your Guide to Libra Season Libra season brings an energy that’s sociable, harmonious, and fair-minded.
By Claire Comstock-Gay
lfw spring 2024 Yesterday at 2:38 p.m.
Skepta Just Wants to Get the Pleats Right We spent 20 minutes with the British artist as he strived to get his collection runway-ready.
mfw spring 2024 Yesterday at 12:31 p.m.
The Best Street Style From Milan Fashion Week See our favorite looks from outside the shows.
celebrity Yesterday at 12:00 p.m.
A Bianca Censori Primer The woman inside the pantyhose.
the approval matrix Yesterday at 12:00 p.m.
The Sun Sets on WFH Our guide to what’s highbrow, lowbrow, brilliant, and despicable.
explainers Yesterday at 11:50 a.m.
What We Know About the Russell Brand Rape Allegations Several women have come forward with accounts of sexual assault and abuse by the comedian.
gone sale-ing Yesterday at 11:40 a.m.
10 Things You Don’t Have to Pay Full Price for This Week Deals from Outdoor Voices, Everlane, Ulta, and more.
crime Yesterday at 10:47 a.m.
A One-Year-Old Died From a Suspected Fentanyl Overdose at a Bronx Day-Care Police says they found a stash of the drug under a trap door, near a play area for the children.
the group portrait Yesterday at 8:00 a.m.
Give the Liberty Their Crown How New York’s WNBA team became the hottest ticket — with the rowdiest crowd — in town.
By Emma Carmichael
it girl Yesterday at 8:00 a.m.
Este Haim Is Letting Her Freak Flag Fly Haim’s bassist, vocalist, and eldest sister knows exactly what she likes.
the body politic Yesterday at 8:00 a.m.
The Return of the Marriage Plot Why everyone is suddenly so eager for men and women to get hitched.
power Sept. 21, 2023
A Designer Is Now Suing Lizzo for Working Conditions on Tour Asha Daniels alleges she worked 20-hour days without breaks in an “unsafe, sexually charged workplace culture” on the singer’s Special Tour.
back to college Sept. 21, 2023
Five Students Show Us Their First-Day-of-School Outfits One student’s approach to back-to-school dressing is “put-together but not in a try-hard way.”
More Stories
  • Style
  • Self
  • Culture
  • Power
  • About The Cut
  • About New York Magazine
  • Newsletters
  • Help
  • Contact
  • Press
  • Media Kit
  • We’re Hiring
  • Privacy
  • Terms
  • Ad Choices
  • Do Not Sell My Info
  • Accessibility
The Cut is a Vox Media Network. © 2023 Vox Media, LLC. All rights reserved.