Outfits for Every Winter Occasion

outfits for winter occasions blog

Winter events and fun occasions call for new outfits! Read our latest blog post for outfit ideas for winter weddings, ice skating, ski trips, and more. Plus, you’ll find great wardrobe staples for winter that you’ll be able to wear on repeat. Cozy up in our bestselling lounge pants, start the New Year is our go-to leggings, and celebrate special events in our best dresses. 

New Year’s Day 5K 

what to wear for a 5K marathon

Our Athleisure Shop has all the running outfit essentials you need whether you are looking for what to wear for a 5K or marathon, or just trying live a more active lifestyle. 

Ice Skating 

ice skating outfits

One of our favorite winter activities, bundle up for ice skating with vests, jackets, and our favorite patch sweatshirts. 

Boxing Day Shopping 

outfits for shopping

Something about a comfy and cute outfit makes shopping more fun! If you’re venturing out for those after Christmas deals, throw on a staple hoodie or shacket as the perfect layering pieces. 

Coffee Date 

coffee lover sweatshirts

This one’s for our caffeine queens! Any of our coffee sweatshirts are perfect outfits for coffee lovers and they’re a staple you’ll wear year-round. 

Ski Trip 

winter graphics for ski trip

If you’re packing for a ski trip this winter, be sure to add all the layering styles to your suitcase: winter graphic sweatshirts, long sleeve-t-shirts – all with the the perfect statements for such a trip. 

Disney Trip 

what to wear to disney

If you’re heading to warmer weather for a family disney trip, we recommend leggings with pullovers plus our bestselling belt bags for the best on-the-go outfits! Check out the full blog for What to Wear to Disney!

Work Conference 

what to wear to work

If you’re traveling for business this season, be sure to check out our work wear essentials including the comfiest dress pants, trendy blazers, and effortless button up blouse. You’ll never wonder what to wear to work again! Get more workwear outfit ideas with our full blog

Winter Wedding 

wedding guest outfits

Searching for what to wear to a winter wedding? Here’s some of our favorite picks! Be sure to check out the full blog: What to Wear to a Winter Wedding at pinklily.com 

Movie Marathon 

movie marathon loungewear

Whether you are enjoying your favorite Christmas movies or enjoying a Hallmark movie marathon, you’ll find our loungewear to be another staple you’ll want to add to your closet. Just add hot cocoa and popcorn to complete the perfect night in. 

New Year’s Eve 

new year's eve outfits

Countdown to midnight with our best New Year’s Eve outfit ideas. Check out the full blog for even more New Year’s Eve party outfit inspo! 


what we'd wear to... winter edition

Once again, we took to Instagram to get the details straight from our followers on what kind of #ootd inspo you need for winter! Events and occasions are always the perfect excuse for a new outfit!

School Christmas Party

school christmas outfit

Any Christmas event calls for some festive hues! We love the Days Away Ribbed Cuffed Sleeve Sweater paired with any of our black denim to dress up the outfit. Add some black booties to complete the look!

NYE Party

new year's eve outfits

So many dressy options to choose from for New Year’s! Save your Memories Hunter Green Satin Cowl Neck Midi Dress is a glamorous choice. You can’t go wrong with an LBD like the Leaving Late Black Mesh Sleeve Square Neck Dress. If you’re wanting a more modest option, check out the Filled with Happiness Black Dress. Be sure to check out our Dressy Holiday Collection for even more sparkly options.

High School Reunion

high school reunion outfit

Noticed By You Black Satin Jumpsuit is a bold, power suit for such an event. If you’re looking for an outfit to dance the night away, we love the Relive Last Night Velvet Black Dress. The sweetheart neckline on this LBD is elegant and stylish.

21st Birthday

21st birthday outfit

Matching Sets are one of our favorite outfit options because they always stand out from the crowd. Your 21st birthday is the perfect occasion to really make a statement with your outfit! Brand new to pinklily.com, you’re sure to love the Better Days Black/White Plaid Sweater and Skirt combo.

Date Night

date night outfit

A chilly date night calls for layers upon layers! You Got It Tan Striped Turtleneck Sweater Dress is a staple style to add to your winter wardrobe. Layer over it with the No Doubts in Mind Cream Belted Coat for the complete outfit. For an anniversary date night, we love a dressier option for the special occasion. Takeover The Night Midi Dress has flattering cut out detailing.

Office Christmas Party

office christmas party outfit

For the annual work Christmas dinner, we once again go for those holiday hues. Exclusive Invites Green Leopard Print Wrap Dress is a fierce option. Found My Forever Burgundy One Shoulder Maxi Dress is another stunning option. If you’re wanting something a little more casual, the Sparks Fly Midi Dress is perfect and can easily be layered with any cardigan or jacket.

Winter Baby Shower

winter baby shower outfit

Winter blue hues are adorable for baby showers. Escape Today Blue Tweed Jumper Dress paired over a white bodysuit is one of our go-to outfit ideas. If you’re leaning towards pink for the occasion, Don’t Blink Rose Collared Midi Dress is the perfect style and material for a winter event.

See the Christmas Lights

winter outfit essentials

One of our favorite holiday traditions calls for all the layers! The Always Cold Mauve Sweatshirt is certainly fitting for the occasion. Pair it with the Just an Expression Ivory Hooded Puffer Jacket and the Tami Fleece Booties to stay warm. You can also choose of our many shackets as layering pieces. The Deserve the World Corded Shacket is available in solid color options like blue, charcoal, and ivory - making it easy to pair with whatever winter gear you own!

Cold Weather Gear

winter outdoor activities outfit

No winter wardrobe is complete without a puffer jacket. Make You Believe Brown Cropped Animal Print Jacket is a warm favorite of ours. Leggings are great for layering in colder weather. Finish off the outfit with a cozy beanie and scarf.

Keep an eye out for more winter wonderland styles debuting in our Ski Edit on December 17th!