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Classy-Casual Holiday Party Outfit Ideas for Him & Her

‘Tis the season for a ton of holiday events. If you’re in search of stylish yet effortless holiday party outfit ideas, you’re in the right spot. 

Whether you’re getting ready for your family gathering, annual office celebration, or hosting a party with friends, you’ll need to nail down your classy-casual holiday party style. 

To make the most of your winter wardrobe, we believe your best bet is to choose classic layering pieces that are easy to mix and match. 

Below, we’re sharing our favorite festive holiday party fashion picks below, including matching sweaters, pullovers, vests, and pants. All of these ideas will give you the high-quality comfort to keep your focus on what truly matters—spending time with loved ones. 

Get a glimpse at our on-trend outfit options for the 2023 holiday party season.


Trending Holiday Party Layering Styles for Her in 2023


Stretch Oxford Stripe Women’s Long Sleeve Dress Shirt 


Cutter & Buck Stretch Oxford Stripe Womens Long Sleeve Dress Shirt

Simple and sharp, you can never go wrong with a women’s dress shirt. This timeless look features subtle stripes and casual easy-to-roll sleeves, making it exceptionally versatile for every party. The textured cotton blend fabric is easy to move in and will stay wrinkle-free all day.  Pair under a v-neck sweater for extra warmth, or consider some of the styles ahead.

Dress Shirt Features:

  • Textured cotton blend stretch fabric
  • 64% cotton, 34% polyester, 2% spandex
  • Mercerized & wrinkle-free fabric finish
  • C&B pennant on inside placket
  • Machine wash

Price: $100.00 - Select colors $14.00!

Shop the Stretch Oxford Stripe Women’s Long Sleeve Dress Shirt 


Women’s Lakemont Tipped Half-Zip Sweater

Cutter & Buck Womens Lakemont Tipped Half-Zip Sweater for a classy casual holiday party look

Highly rated for good reason, this cozy women’s sweater is equally comfortable and chic. The contrast tipping adds a touch of sophistication, and the half zip allows you maximum layering opportunities. Keep it zipped to show off the mock neck, or wear it as a v-neck to show off a style underneath, like a crisp button-up dress shirt. And to encapsulate the holiday spirit, it comes in a few festive colors such as deep red, green or blue.

Sweater Features:

  • 80% cotton, 17% nylon, 3% spandex
  • Half zip mock neck
  • English shoulder
  • Contrast tipping at collar & sleeve hem
  • Machine wash

Price: $110.00 - Select colors $44.00!

Shop the Women’s Lakemont Tipped Half-Zip Sweater 


Mainsail Sweater Knit Womens Full Zip Vest

Cutter & Buck Mainsail Sweater Knit Womens Full Zip Vest for holiday parties

Completely constructed with our signature warm sweater fleece, this is the women’s vest to grab for Christmas parties on chilly winter days. It looks fantastic over a button-up or sweater and comes with secure zip front pockets to keep your belongings, or mittens, safe and secure.

Vest Features:

  • 100% Polyester Sweater Fleece
  • Exceptionally warm brushed fleece interior with sweater-knit exterior
  • Princess seams and contoured hemline create a flattering fit & shape
  • Secure zip front pockets
  • Machine wash

Price: $125.00 - Ships free!

Shop the Mainsail Sweater Knit Womens Full Zip Vest 


Women’s Response Pants 

Cutter & Buck Womens Response Pants for holiday parties

To tie your holiday party look together, try these agile women’s response pants. Made with a four-way stretch, you will be able to move with ease for long parties, or if you’re stopping by a few. These straight-leg sleek pants also give the gift of storage with side cargo pockets, front hidden pockets, and a back welt pocket. 

Pant Features:

  • 85% nylon, 15% spandex
  • 4-way stretch fabric
  • Moisture wicking
  • Front hidden zip pockets
  • Machine wash

Price: $125.00 - Select colors $24.00! 

Shop the Women’s Response Pant 


Popular Holiday Party Styles for Him in 2023


Easy Care Stretch Gingham Mens Long Sleeve Dress Shirtasy Care Stretch Gingham Mens Long Sleeve Dress Shirt for holiday parties

Nothing says a holiday party quite like a plaid print. This men’s dress shirt offers crips comfort with its smooth and stretchy cotton blend material. And no wrinkles to worry about, as it’s made with a protective finish to keep your look sharp. This shirt looks great tucked into dark jeans or dress pants. And to elevate the look, add your favorite belt. 

Dress Shirt Features:

  • 64% cotton, 33% polyester, 3% spandex
  • Yarn dye plain weave stretch fabric  
  • Wrinkle-resistant finish
  • Plaid pattern
  • Machine wash

Price: $105.00 - Select colors $60.00!

Shop the Easy Care Stretch Gingham Mens Long Sleeve Dress Shirt 


Men’s Douglas Half-Zip Mock Sweater

Classy casual Douglas Half-Zip Sweater Mock

For a warmer option, we recommend this men’s sweater, crafted with cozy merino wool. It’s a classic festive staple for any party and looks sharp over a bright button-up or a polo. And if you’re looking for extended sizing options, this is available in our big & tall styles

Sweater Features:

  • 50% acrylic, 50% merino wool fabrication
  • 1x1 rib collar, cuff, and bottom opening
  • Linked seams
  • Fully fashioned construction, ottoman-stitch detail
  • Machine wash

Price: $150.00 - Ships free!

Shop the Men’s Douglas Half-Zip Mock Sweater 


Men’s Lakemont Sweater Vest

Cutter & Buck Lakemont Sweater Vest for holiday parties

This men's vest offers exceptional comfort and durability and is designed with just the right blend of cotton, nylon, and spandex. Easy to pair with a button-up or quarter-zip, this vest offers the exact style element to create a polished party appearance. And for a bolder look, choose your favorite patterned style underneath. 

Vest Features:

  • 80% Cotton 17% Nylon 3% Spandex
  • Tubular self-trim at neck and armhole
  • Contrast stripe detail at the inside neck
  • English shoulder
  • Machine wash cold delicate; lay flat to dry

Price: $90.00 - Ships free!

Shop the Men’s Lakemont Sweater Vest 


Men’s Bainbridge Flat Front Pant

Men's Cutter & Buck Bainbridge Flat Front Pant

Clean and classic, these moisture-wicking men’s pants will match any holiday party style of your choice. We love these for their modern, tailored fit, and breathable fabric. These pants come in cool earth tones so you can easily match them with a bright festive color. 

Pant Features:

  • Breathable, moisture-wicking CB DryTec
  • 88% polyester, 12% spandex
  • Moisture-wicking
  • Piped front pockets, back welt pockets
  • Machine wash

Price: $120.00 - Select colors $89.00! 

Shop the Men’s Bainbridge Flat Front Pant 


There’s More Holiday Classy-Casual Styles to Shop

While you’ve seen a few of our go-to party picks, we have more holiday-style staples to explore. For ideas, try checking out our clothing gift lists. No matter what you end up choosing to wear, we hope you have fun getting in the spirit, and enjoy all your celebrations!