17 Holiday Party Looks That Will Never Go Out of Style
17 Holiday Party Looks That Will Never Go Out of Style
By Jane Dunn — December 9, 2024
The holiday season brings a host of festive occasions, from glamorous galas to intimate gatherings.
Article cover image from Dupe Photos.
When it comes to dressing for these events, there’s a temptation to go for trendy, of-the-moment pieces. However, timeless elegance will always trump fleeting fashion. Whether you're celebrating Christmas with family, ringing in the New Year with friends, or attending an elegant cocktail reception, finding the perfect outfit is essential.
From sophisticated metallic gowns to cozy yet elegant cashmere sweaters, these 17 outfits will have you radiating confidence and festive cheer all season long.
1. The Little Black Dress
The quintessential holiday outfit, the Little Black Dress, never goes out of style. Whether you opt for a sleek midi or a flattering mini, this classic staple serves as the perfect canvas for accessorizing. Go for clean lines, a structured silhouette, or add a contemporary twist with details like a velvet finish or subtle metallic thread.
Elevate the look with bold, colorful jewelry and a slick back bun or a red lip for a refined yet festive vibe.
2. The Satin Slip Dress
Satin has a lustrous sheen that makes it the perfect fabric for holiday parties. A satin slip dress, particularly in a jewel-toned hue like emerald, ruby, or sapphire, exudes understated glamour. Its simple, fluid shape makes it both timeless and flattering for a wide range of body types.
Pair it with strappy heels and delicate jewelry for an effortlessly chic look that transitions beautifully from Christmas to New Year's.
3. The Tailored Tuxedo Suit
The tuxedo suit is a chic and bold choice for those who prefer a sharp, modern silhouette. A tailored tuxedo, whether in classic black or rich midnight blue, combines the sophistication of menswear with the elegance of evening attire. Look for sleek, well-structured lines, a satin lapel, and a tailored fit.
Pair with a silk camisole underneath, pointed-toe heels, and a bold red lip for a fresh take on classic glamour.
4. The Sequin Gown
There’s something undeniably festive about sequins, and this season, sequin gowns are an iconic way to shimmer through the holiday season. Go for a floor-length gown in gold, silver, or black, with a form-fitting silhouette or a dramatic, flowing skirt for maximum impact.
Keep your accessories simple — let the gown shine with sleek heels and minimal jewelry.
5. The Velvet Midi Dress
Velvet has become synonymous with holiday style, and for good reason. Its rich texture and opulent look make it a perfect choice for winter festivities. A velvet midi dress, with a figure-flattering silhouette and subtle detailing like puff sleeves or a wrap-around design, feels both luxurious and timeless.
Add a delicate clutch and gold accents to maintain a polished, yet festive look.
6. The Feathered Detail Dress
Feathers make a bold statement without feeling too over-the-top, and they are a chic and timeless holiday trend. Whether used as an accent on the sleeves, hemline, or bodice, feather details add texture and whimsy to any outfit. A feathered cocktail dress in deep burgundy or classic black will always feel appropriate for any festive occasion.
Pair with simple black pumps and a refined clutch to keep the focus on the feathers.
7. The Brocade Dress
Brocade fabrics, with their intricate patterns and metallic threads, have long been associated with opulence. A brocade dress, whether in a fit-and-flare design or a sleek sheath cut, is an elegant choice for formal holiday events. Its timeless appeal comes from its rich, woven texture and regal aesthetic.
Keep jewelry minimal, allowing the rich texture of the fabric to take center stage.
8. Satin Slip Skirt and Cashmere Sweater
This effortlessly chic combination pairs the flowing elegance of a satin slip skirt with the softness and comfort of a cashmere sweater. Opt for jewel-toned colors like emerald or ruby, and finish the look with sleek heels and delicate jewelry for a polished yet approachable outfit.
Complete the look with knee-high boots and a structured handbag for a sophisticated yet cozy holiday vibe.
9. The Silk Blouse and Tailored Pants
A silk blouse is the ultimate in understated luxury, making it an ideal choice for holiday gatherings. Pair it with high-waisted, tailored trousers in a classic color — black, navy, or charcoal — to create a balanced and elegant look. A blouse with delicate details like a bow tie-neck or pleats gives the outfit an air of refined sophistication.
Pair with pointed heels and a clutch to keep the look sleek and timeless.
10. The Faux Fur Stole
While not a full outfit, a luxe faux fur stole or wrap can instantly elevate any holiday look. Drape it over a dress, suit, or tailored jacket to add instant glamour and warmth. Faux fur in soft shades like ivory, taupe, or classic black adds sophistication while staying in line with the season’s opulent mood.
Pair it with a metallic or satin dress for a contrast of textures, ensuring you stay warm without sacrificing style.
11. The Draped Silk Gown
A silk gown, draped to perfection, offers an elegant look that never goes out of style. Opt for a fluid silhouette that gently cascades to the floor for an ethereal effect. Whether you choose a minimalistic design or subtle ruching, such gowns guarantee that you'll turn heads at any black-tie event.
Pair with statement earrings and a sleek, low bun for a sophisticated and classic finish.
12. The Sequin Two-Piece Set
Two-piece sets are a chic and modern alternative to dresses, offering versatility and style in equal measure. When crafted in sparkling sequin fabric, especially in metallic shades like gold, silver, or deep bronze, they effortlessly capture the essence of festive glamour. A sequin two-piece set—whether with a cropped top and high-waisted skirt or tailored pants — combines sophistication with a playful edge, making it the perfect choice for holiday parties and celebrations.
Keep the accessories minimal and opt for sleek, metallic shoes to let the bold sequins take center stage. A simple clutch or delicate jewelry will allow the dazzling texture of the set to shine without distraction.
13. The Chic Midi Skirt and Cashmere Sweater
Midi skirts are a staple of timeless elegance, and they work beautifully for holiday parties. Opt for a metallic pleated midi skirt paired with a soft cashmere sweater. The contrast of the fluid skirt and cozy sweater is an effortlessly chic combination that feels festive without trying too hard.
Pair with heeled ankle boots or classic pumps to keep the look grounded yet elegant.
14. The Tailored Shift Dress
A shift dress is a wardrobe staple that can be worn across seasons, and its clean lines and minimal design make it ideal for holiday parties when paired with the right accessories. A shift dress in a bold color like scarlet or deep green feels festive while maintaining a refined, timeless appeal.
Add statement earrings and a delicate bracelet to enhance the sophisticated nature of the dress.
15. A-Line Wool Coat and Heeled Boots
A luxurious wool coat in a neutral tone, such as camel or charcoal grey, can be just as glamorous as a dress when paired with the right accessories. Team it with tall, heeled boots and a statement scarf for a look that transitions from the chilly outdoors to a festive indoor affair with ease.
16. The Classic Midi Dress with a Modern Twist
A timeless silhouette, the midi dress, will never go out of style. This season, embrace classic cuts with a modern twist — think high necklines, open backs, or structured pleats. A midi dress in a rich velvet or silk fabric can transition effortlessly from Christmas dinner to New Year's Eve.
Pair with a statement belt or vintage-inspired jewelry to add a unique touch to the timeless design.
17. The Plaid Cocktail Dress
Plaid can be an unexpectedly chic choice for the holidays. Choose a plaid pattern in rich colors like burgundy, navy, or deep green for a sophisticated yet festive look. A plaid dress with a flattering A-line or wrap silhouette offers a classic, feminine shape that's perfect for a holiday cocktail party.
Keep accessories simple with metallic heels and a refined clutch to let the plaid pattern speak for itself.
When it comes to holiday dressing, the key is timelessness — investing in pieces that transcend trends and can be worn season after season. From the elegance of the little black dress to the opulence of brocade and velvet, these 17 outfits embody sophistication, luxury, and festive cheer. This holiday season, choose pieces that make you feel confident, comfortable, and forever chic. With these 17 holiday looks, you’ll have every reason to celebrate in style, knowing that elegance is always in fashion
Keep reading Square Magazine for more 25 Days of Square content and be sure to follow Square Magazine on Instagram and TikTok for exclusive content.
All images belong to their respective owners.