10 Essentials for Your Chic Holiday Wardrobe

Holiday Outfits Feature

I get tired of wearing the same thing day in and day out, but to be honest, there’s really no reason to get dressed up on a frequent basis. That’s why when the holidays roll around, I get excited to upgrade my wardrobe choices a bit and get outside my daily comfort level. However, after taking last year’s holiday festivities off, I’ve found that most of my special occasion wear is a bit outdated. And let’s face it, getting something new and fashionable is a fun way to ring in the holiday season – and subsequently, a new year! 

There are some basics that you should have in your wardrobe so that you’ll be ready for any special occasion – from winter formals to holiday parties. All it takes are a few dressy basics to mix and match your way to glamorous holiday outfits! Here are the key items we recommend you keep in your closet so you’ll be prepared for anything.

Happy Holiday dressing!! 

Little Black Dress

One key item to include in any wardrobe is a perfect little black dress. The trendiest ‘midi’ lengths fall modestly between below the knee and mid-calf, and the ‘classic’ LBD hemline is right at the knee. Satin, velvet, jersey, and crepe are some of the best fabrics for this style. Looking for arm coverage? Here are three options that will fit any situation and are easy to dress up or keep casual. They definitely bring the glam and provide both comfort and fashion – a winning combination. 

If you prefer to go with a sleeveless option, you’ll find seemingly endless opportunities to dress your LBD up with a cardigan, jacket, or blazer. And don’t forget to accessorize! 

Fraiche By J Empire Waist Long Sleeve Dress
Fraiche By J Empire Waist Long Sleeve Dress, $99
JM Claughlin Bertha Dress
JM Claughlin Bertha Dress, $228


onlypuff Fishtail Dresses
Onlypuff Fishtail Dresses, $40.89

Sparkly Top

A sparkly top is festive enough to stand on its own, and an embellished cardigan looks especially fresh right now. You can pair your top with black trousers or a straight skirt, then pull back your hair and apply party-ready red lips for a classic look.

Aqua Long Sleeve Sequin Top
Aqua Long Sleeve Sequin Top, $62.40
Vince Camuto Balloon Sleeve Sequin Blouse
Vince Camuto Balloon Sleeve Sequin Blouse, $99
Open Edit Sequin Wrap Top
Open Edit Sequin Wrap Top, $69

Soft Trousers

Trousers are en vogue for any part of your day. Plaids and corduroys make great daytime selections, but for the holidays, it is best to keep the bottoms simple because of all the other bling head-to-toe. Black and winter white are faves – and festive fabrics, like velvet, can make a fashion statement all on their own.

INC Petite Velvet Skinny Pants, Created for Macy's
INC Petite Velvet Skinny Pants, Created for Macy’s, $29.99
Loft Velvet Pull On Slim Pants
Loft Velvet Pull-On Slim Pants, $79.50
Wide Tuck Wool-Blend Pants
Wide Tuck Wool-Blend Pants, $148

Dressy Wrap

A beautiful shawl does more than just look good: it can cover bare shoulders, too. Embroidered styles go great with basic strapless dresses; velvets and fringed pieces add richness to separates. Stick with a shawl in approximately the same fabric “weight” as your outfit (you wouldn’t want to pair a heavy velvet piece with a gossamer gown).

Ann Taylor Faux Fur Wrap
Ann Taylor Faux Fur Wrap, $98
Calvin Klein Satin-Trim Chiffon Evening Wrap
Calvin Klein Satin-Trim Chiffon Evening Wrap, $22.50
Lily Pulitzer Autumn Wrap
Lily Pulitzer Autumn Wrap, $78

Perfect Clutch Bag

Complete your holiday outfits with a sophisticated clutch bag. Look for clean lines with subtle details (like gold or silver hardware) to get the most mileage. Some styles have a short strap to go over your shoulder or a loop to hang around your wrist, but holding a dainty bag in your hand is still the chicest way to go.

INC Teresa Mother of Pearl Clutch
INC Teresa Mother of Pearl Clutch, $99.50
BHLDN Torelle Bag
BHLDN Torelle Bag, $68
Kate Spade tonight crossbody clutch
Kate Spade tonight crossbody clutch, $89

Festive Pumps/Sandals

A great high-heeled shoe will go with everything from pants to little black dresses. Can’t wear heels? No need to fret! There are some fabulous glitzy flats and kitten heels for you to choose from. Fabric is the key element and woven sparkly fabrics make evening shoes adaptable to many occasions.

Naturalizer Tiff Block Heel Sandal
Naturalizer Tiff Block Heel Sandal, $125
Badgley Mischka Cher II Pumps
Badgley Mischka Cher II Pumps, $265
INC Zitah Embellished Pointed Toe Pumps
INC Zitah Embellished Pointed Toe Pumps, $89.50

Brocade or Velvet Jacket

The dressy jacket is a staple because it classes up everything from simple white blouses to plain black trousers. Burn-out and embroidery are two finishes that add interest; look for traditionally rich velvet colors like black and burgundy.

WHBM Velvet Studio Blazer
WHBM Velvet Studio Blazer, $180
Karen Kane Animal Pattern Jacquard Blazer
Karen Kane Animal Pattern Jacquard Blazer, $179
WHBM Velvet Studio Blazer
WHBM Velvet Studio Blazer, $180

Blazing Fashion

This year you’ll find oversized blazers trending at every holiday party you attend. They work well with a pair of slacks and a nice blouse or with a festive skirt. Are you going to a more casual affair? Don’t hesitate to wear a pair of fashionable jeans and elevate your look with a blazer and a pair of trendy heels. 

White House Black market Herringbone Blazer
WHBM Herringbone Blazer, $160
Macy's Women's The Oversized Blazer Jacket
Macy’s Women’s The Oversized Blazer Jacket, $41.99
Tommy Hilfiger Plaid Topper Jacket
Tommy Hilfiger Plaid Topper Jacket, $149

Fabulous Earrings

If you can swing it (and there are plenty of good buys out there), real diamonds are the only way to go. If that’s not your style go for colored stones and earrings with swagger. Hoops, drops, and studs are all popular styles. Just pair your earrings to your updo (the more pulled back/up your hair, the longer the earring).

Alta Capture Mini Link Earrings
Alta Capture Mini Link Earrings, $101.25
Kate Spade pearl caviar statement earrings
Kate Spade pearl caviar statement earrings, $128
Garden Party Earrings
Garden Party Earrings, $48

Don’t Forget The Details 

There’s always room to elevate your outfit after bringing together the staple parts of your wardrobe. A flashy necklace can kick up the look of an LBD or bring together your blouse/blazer combination. And never underestimate how much flash a little hair accouterment can bring to your look. Have some fun with it! We took a year off; this year, go big! 

Calvin Klein Women's Unified Choker
Calvin Klein Women’s Unified Choker, $146.43
Lagos 'Luna' Long Pearl Necklace, $375
Lagos’ Luna’ Long Pearl Necklace, $375
LELE SADOUGHI Mix Metallic Knotted Headband
LELE SADOUGHI Mix Metallic Knotted Headband, $75

Now that you’ve got the key pieces for your chic holiday outfits you can feel confident attending any party or get-together. Have some fun with your selection and enjoy your time out with friends and family. 

Read Next: 

Holiday Beauty Gift Guide

Fashion to Imitate