Holiday parties shouldn’t mean squeezing into uncomfortable outfits that leave you counting down the minutes until you can change. This season, the fashion world has embraced what we’ve all been secretly wishing for: oversized silhouettes that let you actually enjoy those holiday cookies without worrying about restrictive waistbands. From chunky knit sweaters to relaxed blazers and flowing wide-leg pants, oversized pieces have moved beyond loungewear to become the foundation of seriously chic party looks. The secret? It’s all about intentional styling—pairing that cozy oversized sweater with sleek accessories, tucking in strategically, or balancing proportions with fitted bottoms. In this guide, you’ll discover 15 ways to rock oversized Christmas party outfits that prove comfort and style aren’t mutually exclusive, complete with shopping recommendations, styling hacks, and tips for looking polished without feeling restricted.
1. Oversized Fair Isle Sweater with Sequin Skirt
The unexpected pairing of cozy knitwear with glamorous sequins creates that perfect holiday balance between comfortable and party-ready. This combination lets you stay warm while still bringing serious festive energy.
Choose a classic Fair Isle or holiday-patterned sweater in rich jewel tones, pair with a black or metallic sequin midi or pencil skirt, and finish with pointed-toe flats or low heels. The oversized sweater provides comfort and warmth while the sequins add instant glamour.
Shop Fair Isle sweaters at J.Crew ($80-120), Target ($30-45), or Ralph Lauren for investment pieces ($150-200). Find sequin skirts at Old Navy ($40-60), Zara ($50-70), or Nordstrom ($80-120). This outfit works beautifully for office parties, family gatherings, or casual cocktail events.
Tuck just the front of your sweater loosely into the skirt waistband for a more polished silhouette.
2. Chunky Knit Turtleneck with Wide-Leg Trousers
Nothing beats a cashmere turtleneck during the holidays—it’s the perfect dress-casual option that reads as both sophisticated and approachable for various holiday occasions.
Select an oversized cream, camel, or burgundy turtleneck sweater, pair with high-waisted wide-leg trousers in a complementary neutral, and complete with leather loafers or ankle boots. The combination creates elegant vertical lines despite the oversized top.
Invest in quality turtlenecks from Everlane ($100-150), Uniqlo ($50-80), or splurge on cashmere versions from Naadam ($120-180). Pair with trousers from Mango ($60-90), Banana Republic ($80-110), or J.Crew ($90-130). This versatile outfit transitions seamlessly from holiday brunches to evening dinners.
Add statement gold jewelry or a silk scarf to elevate the neutral palette without overwhelming it.
3. Oversized Blazer as a Dress
Channel major boss energy by wearing an oversized blazer as a standalone dress—a trend that’s both daring and surprisingly wearable for confident party-goers.
Choose a structured oversized blazer in velvet, tweed, or metallic fabric, wear it solo with nude or black tights underneath, and finish with pumps or T-bar heels. The blazer-as-dress creates a sleek, sophisticated silhouette that turns heads.
Shop oversized blazers at Zara ($80-120), H&M ($60-90), or invest in designer options from Mango ($120-160). This look works perfectly for trendy holiday cocktail parties or New Year’s Eve celebrations where you want to make a statement.
Keep jewelry minimal and let the blazer be the star—add just a pair of statement earrings.
4. Oversized Cardigan with Velvet Leggings
Velvet leggings paired with an oversized cardigan prove that you can absolutely wear stretchy pants to a holiday party when styled correctly with luxe fabrics.
Layer a long oversized cardigan or duster in a neutral tone over a fitted tank or camisole, pair with velvet leggings in burgundy, forest green, or black, and complete with ankle boots or ballet flats. The cardigan provides coverage while the velvet adds occasion-appropriate texture.
Find quality cardigans at Old Navy ($40-60), Madewell ($90-130), or Anthropologie ($120-180). Shop velvet leggings at Spanx ($90-120), Nordstrom Rack ($30-50), or Amazon ($20-35). This outfit thrives at casual family gatherings, holiday movie nights, or low-key friend get-togethers.
Add a festive brooch or holiday-themed earrings to amp up the seasonal spirit.
5. Shiny Pinstripe Oversized Suit Set
Image via PureWow
For those who prefer elevated alternatives to sequins or gowns, an oversized suit with a shiny pinstripe delivers sophistication with a modern relaxed fit.
Select a matching oversized blazer and wide-leg pant set in metallic pinstripe or subtle shimmer fabric, style with a fitted camisole or silk tank underneath, and finish with strappy heels or pointed-toe mules. The suit creates polished structure while remaining comfortable.
Shop suit sets at Eloquii ($120-180 for the set), ASOS ($80-120), or Zara ($100-150). This outfit works perfectly for corporate holiday parties, upscale dinner events, or any occasion requiring business-festive attire.
Roll the blazer sleeves slightly for a more relaxed, contemporary vibe that softens the formality.
6. Oversized Christmas Sweater with Faux Leather Leggings
Image via Wardrobe Oxygen
Transform the humble ugly Christmas sweater from novelty to chic by pairing it with sleek faux leather leggings that ground the playful top.
Choose your favorite oversized holiday sweater—whether it features reindeer, Christmas trees, or festive patterns—pair with fitted faux leather or coated leggings, and complete with ankle boots or over-the-knee boots. The contrast between cozy knit and sleek leather creates interesting texture play.
Find Christmas sweaters at Target ($25-40), Old Navy ($30-50), or Tipsy Elves for statement pieces ($50-80). Shop faux leather leggings at Spanx ($90-110), Commando ($80-100), or Amazon ($25-40). This outfit works for ugly sweater parties, casual office celebrations, or weekend holiday shopping.
Add festive earrings shaped like ornaments or candy canes for extra holiday cheer without overdoing it.
7. Oversized Button-Down with Sequin Pants
Image via The Huntswoman
Flip the script by keeping your top casual and letting your bottoms bring the sparkle—sequin pants make a bold statement when balanced with classic shirting.
Select an oversized white or cream button-down shirt, tuck it loosely into cigarette-cut or wide-leg sequin pants, and finish with pointed-toe heels or strappy sandals. The combination feels editorial and modern while staying party-appropriate.
Shop oversized button-downs at Everlane ($70-100), H&M ($30-50), or Equipment for silk options ($200-250). Find sequin pants at Eloquii ($80-120), Anthropologie ($120-150), or ASOS ($60-90). This outfit shines at cocktail parties, New Year’s Eve celebrations, or any event where you want to stand out.
Keep accessories simple—the sequin pants already make a strong statement that doesn’t need competing elements.
8. Oversized Sweater Dress with Tights and Boots
Image via topsfordays
The sweater dress is the ultimate one-and-done holiday outfit that requires minimal styling effort while delivering maximum cozy-chic impact.
Choose an oversized sweater dress in a festive color like cranberry, forest green, or winter white, layer with fleece-lined or patterned tights, and finish with knee-high or over-the-knee boots. The dress provides full coverage and warmth while the boots add structure.
Shop sweater dresses at Amazon ($30-50), Target ($35-60), or Anthropologie ($110-160). Pair with tights from Spanx ($20-30) or Swedish Stockings ($30-40). This versatile outfit works for everything from brunch to evening parties and travels well for holiday trips.
Add a statement belt at the waist to define your silhouette and prevent the oversized dress from overwhelming.
9. Oversized Teddy Coat Over Simple Dress
Image via Style Rave
Sometimes the outerwear IS the outfit—an oversized teddy coat transforms even the simplest dress underneath into a fashion-forward holiday look.
Layer a plush oversized teddy coat in cream, camel, or black over a fitted midi or mini dress, add tights if needed for warmth, and complete with heeled ankle boots or pumps. The coat provides warmth and makes a strong style statement.
Find teddy coats at Abercrombie ($100-150), Zara ($80-120), or Target ($50-80). This layering technique works beautifully for outdoor holiday markets, evening parties where you’ll be outside, or any cold-weather celebration.
Choose coats with large lapels or dramatic collars that frame your face and add visual interest.
10. Oversized Knit with Plaid Midi Skirt
Image via PureWow
The combination of chunky knit textures with classic plaid creates a preppy-meets-cozy aesthetic that feels both timeless and current for holiday gatherings.
Select an oversized cable-knit or ribbed sweater in a solid color, pair with a wool plaid midi skirt in traditional holiday colors, and finish with tights and Mary Jane flats or loafers. The mixed patterns and textures create visual interest.
Shop oversized knits at & Other Stories ($80-120), COS ($90-140), or Madewell ($80-110). Find plaid skirts at J.Crew ($90-120), Anthropologie ($100-140), or Zara ($50-80). This outfit works perfectly for daytime holiday events, church services, or family photos.
Tuck just the front of your sweater into the skirt to maintain the oversized vibe while showing the skirt’s waistline.
11. Oversized Graphic Sweatshirt with Sequin Skirt
Image via Wardrobe Oxygen
Embrace the high-low mix by pairing a casual graphic holiday sweatshirt with a glamorous sequin skirt—the contrast is what makes this combination unexpectedly chic.
Choose a festive graphic sweatshirt with holiday messaging or graphics, pair with a black or metallic sequin pencil or A-line skirt, and complete with ankle boots or heeled mules. The combination balances playful and polished.
Find graphic sweatshirts at Target ($20-35), Etsy for custom options ($30-50), or Old Navy ($25-40). Pair with sequin skirts from Express ($60-80) or Amazon ($25-45). This outfit works for casual office parties, friend gatherings, or shopping trips where you still want to look festive.
Add simple hoop earrings and let the mix of casual and dressy elements speak for themselves.
12. Oversized Cashmere Sweater with Satin Skirt
Image via Town & Country Magazine
The luxury of cashmere paired with the sheen of satin creates an elevated outfit that feels special occasion without being overly formal or uncomfortable.
Invest in an oversized cashmere sweater in jewel tones like emerald, sapphire, or ruby, pair with a satin midi or maxi skirt in a complementary color, and finish with delicate jewelry and heels or embellished flats. The texture contrast elevates both pieces.
Shop cashmere sweaters at Naadam ($100-200), Everlane ($120-180), or Nordstrom Anniversary Sale for deals. Find satin skirts at Reformation ($110-150), Zara ($50-80), or Anthropologie ($120-160). This sophisticated outfit works for upscale dinner parties, holiday galas, or formal family celebrations.
Choose colors that complement rather than match exactly—emerald with burgundy or navy with gold creates rich depth.
13. Oversized Tuxedo Shirt with Slim Jeans
Image via Stitch & Salt
An elevated white button-down with tuxedo-style pleats becomes instantly party-ready when the oversized proportions are balanced with fitted denim and festive accessories.
Select an oversized white tuxedo-style shirt with pleated details, pair with straight-leg or slim jeans in dark or black wash, and complete with pointed-toe heels and a metallic clutch. Add a velvet hair bow for instant holiday flair.
Find tuxedo shirts at J.Crew ($80-110), Everlane ($90-130), or Equipment ($200-280). Pair with jeans from Levi’s ($80-100), Madewell ($110-140), or Gap ($70-90). This classic-meets-casual outfit works for versatile holiday events from dinner parties to family gatherings.
Add statement earrings and a swipe of red lipstick to take the look from everyday to holiday special.
14. Oversized Lace Top with Wide-Leg Pants
Image via Stitch & Salt
For fancier holiday occasions, an oversized sheer lace top paired with tailored wide-leg pants strikes the perfect balance between romantic and modern sophistication.
Choose a black or jewel-toned oversized lace top (wear with or without a camisole underneath depending on comfort), pair with cropped wide-leg pants in a coordinating color, and finish with strappy heels. The combination feels elegant without being stuffy.
Shop lace tops at Sézane ($120-180), Anthropologie ($100-150), or H&M for budget options ($40-60). Find wide-leg pants at Everlane ($90-120), Mango ($70-100), or Banana Republic ($90-130). This outfit excels at upscale cocktail parties, holiday charity events, or romantic dinner dates.
Add a thin metallic belt and drop earrings to complete the polished, put-together aesthetic.
15. Oversized Bow Sweater with Leather Trousers
Image via Merrick’s Art
Nothing says festive quite like an oversized bow detail—pair this playful sweater with sleek leather pants for a combination that’s both fun and sophisticated.
Select an oversized sweater featuring a dramatic bow detail in cream, black, or blush pink, pair with fitted faux leather or coated trousers, and complete with pointed-toe flats or low heels. The bow adds personality while the leather grounds the look.
Find bow sweaters at Anthropologie ($110-160), Zara ($60-90), or J.Crew ($90-130). Shop leather trousers at Spanx ($90-120), Abercrombie ($80-110), or Commando ($150-200). This outfit works for office holiday parties, dinner events, or any celebration where you want to look polished yet approachable.
Keep accessories minimal to let the bow detail be the focal point—simple studs or hoops are perfect.
Final Styling Tips for Oversized Holiday Outfits
Proportion is Everything: When wearing oversized on top, balance with fitted bottoms. When wearing oversized pants, keep tops more fitted or tuck them in strategically.
Strategic Tucking: A half-tuck (tucking just the front) or side-tuck maintains the oversized vibe while showing some shape and preventing the look from feeling sloppy.
Accessorize Thoughtfully: Statement earrings, delicate necklaces, or a structured bag add polish to relaxed silhouettes without competing for attention.
Undergarments Matter: Seamless undergarments and shapewear can smooth lines under oversized pieces, making them look intentional rather than ill-fitting.
Fabric Quality: Oversized pieces in quality fabrics (cashmere, wool, silk blends) automatically look more elevated than cheaper materials in the same silhouette.
Color Confidence: Don’t shy away from oversized pieces in bold holiday colors—they make just as strong a statement as fitted garments while feeling more comfortable.
Shoe Selection: Pointed-toe shoes, heels, or structured boots help balance oversized proportions and prevent the overall look from feeling too casual.
This holiday season, you don’t have to choose between comfort and style. These 15 oversized Christmas party outfits prove that the most confident looks are the ones where you feel like yourself—just dressed up for the occasion. Whether you gravitate toward cozy sweaters, relaxed blazers, or flowing wide-leg pants, embrace the freedom of oversized silhouettes while keeping things polished with intentional styling. Now go forth and enjoy those holiday cookies without a second thought!
