The holiday season is the best time of year to get dressed up — and the most stressful time to figure out what to wear.
In the space of six weeks, you might have a Thanksgiving dinner, an office party, a weekend of holiday shopping, a family Christmas, and a New Year's Eve celebration. Each one has its own dress code, and almost none of them come with instructions.
This guide takes the guesswork out of it. Here's what to wear to every occasion this season — for her and for him.
Thanksgiving Dinner
Thanksgiving calls for something polished but comfortable. You'll be sitting for hours, moving between the kitchen and the table, and probably going back for seconds.
For her: A knit midi dress or sweater dress with tights and knee-high boots. Or a soft turtleneck with tailored wide-leg trousers in a warm tone like camel or chocolate brown.
For him: A crewneck or quarter-zip sweater over a collared shirt, dark chinos or jeans, and brown leather boots.
Tip: Choose fabrics with a little stretch. Your future self will thank you around pie time.
The Office Holiday Party
Festive, but still professional. The goal is to look like you made an effort without forgetting you'll see these people on Monday.
For her: A satin midi skirt with a fine-knit sweater, or a velvet or jewel-toned dress with a blazer over the shoulders. Finish with a heel or sleek ankle boot.
For him: A tailored blazer over a fine-knit sweater or dress shirt, dark trousers, and polished shoes. Skip the tie unless the dress code says otherwise.
Holiday Shopping in the City
Long days on your feet, crowded sidewalks, and stores that are warmer than the street outside. Layers you can open and close are key.
For her: A long camel coat over a chunky turtleneck, dark jeans tucked into flat knee-high boots, and an oversized plaid scarf. A crossbody bag keeps your hands free for shopping bags.
For him: A charcoal overcoat, navy sweater, dark jeans, and comfortable leather boots — with a wool-blend scarf you can take off indoors.
Christmas With Family
Relaxed, warm, and photo-ready. This is the outfit that ends up in every family picture, so make it one you'll be happy to look back on.
For her: A burgundy or forest green sweater with cream trousers, or a cozy knit set. Add simple gold jewelry for a festive touch.
For him: A cable-knit sweater in cream, red, or green over a button-down, with dark jeans or chinos.
Tip: Coordinate, don't match. Choosing one shared color as a family looks great in photos without feeling forced.
New Year's Eve
The one night of the year where more is more.
For her: A sequin, satin, or metallic party dress — or a sparkly top with tailored black trousers. Throw a long coat over it for the walk between venues, and keep your shoes comfortable enough to last until midnight.
For him: A dark suit or a black blazer over a black knit or crisp white shirt. Clean leather shoes, a good watch, and you're ready to count down.
Find something that shines in our Party Dresses collection.
Three Holiday Rules That Always Work
1. One statement piece per outfit. Sequins, velvet, or bold color — pick one and keep the rest simple.
2. Plan for the coat. In winter, your coat is part of every outfit. A long, neutral coat goes over everything from jeans to a party dress.
3. Shop early. The closer you get to the holidays, the more popular sizes and styles sell out. Picking your outfits in November gives you time to find exactly what you want.
A Final Thought
The holidays aren't about having the perfect outfit for every event. They're about showing up feeling like yourself — warm, comfortable, and ready to enjoy the people around you.
Get the outfit right, and you can forget about it and focus on what matters.
Find your holiday looks in the Winter Collection, Party Dresses, and the Men's Collection at Hollis Ridge.
Published November 2026 | Hollis Ridge