The holidays bring a packed calendar filled with everything from office parties to casual hangouts with friends. Each event calls for a slightly different look, and the right outfit can help you feel both confident and comfortable. Whether you’re dressing up for a festive dinner or keeping it low-key for a laid-back night in, holiday style doesn’t have to be complicated.
With the right mix of polished staples and versatile casual pieces, you can tackle every invitation with ease. Our Stylists put together a men’s holiday outfit guide designed to carry you through the season—no guesswork required.
Holiday Office or Work Party
The office party is your chance to step up your everyday work look and bring a little festive energy to the mix. Think smart, modern and a notch above what you’d typically wear to work.
Start with tailored pants—dark chinos, commuter trousers or slim-fit dress pants. Pair them with a sweater polo layered under a blazer, or keep it crisp with a button-down shirt topped with a cool jacket. Erin adds, “Parties call for a sweater and a blazer combination. The sweater is soft and warm, while the blazer adds structure and professionalism.” Shoes make a big difference here: swap your daily sneakers for leather boots or polished sneakers to strike the balance between professional and approachable.
“Parties call for a sweater and a blazer combination. The sweater is soft and warm, while the blazer adds structure and professionalism.”
-Erin, Stylist
Holiday Gathering Outfit ideas
For holiday gatherings with friends or extended family, aim for elevated casual—something polished but not overly formal.
A classic sweater is always a safe bet. Choose a fine-gauge knit (keeps you warm without overheating) in a holiday tone like maroon or forest green. Or when in doubt, stick with a timeless crewneck in neutral colors. For added styling, Stylist Caro says, “Go for a sweater layered over a button-up with slim chinos—comfortable but sharp enough for photos.” Finish with leather dress shoes or sleek Chelsea boots. This look is easy to put together and feels seasonal without being flashy.
“Go for a sweater layered over a button-up with slim chinos—comfortable but sharp enough for photos.”
-Caro, Stylist
Holiday Family Dinner Outfit
Family dinners often strike that balance between casual and refined. You want to look put together for the photos but still feel comfortable enough to sit around the table.
This is where flannel shirts shine. Choose one in rich holiday hues like burgundy, green or navy, and pair it with colored jeans or chinos. “Dark denim works, too—a darker wash always looks more put together.” Then, add a lightweight jacket—like a bomber or quilted style—for a little extra polish. Finish with clean sneakers or casual boots that keep things relaxed.
“Dark denim works, too—a darker wash always looks more put together.”
-Caro, Stylist
Holiday Get-Togethers Outfits
For casual hangouts like grabbing drinks with friends, watching a holiday game or heading to a low-key bar, jeans are your go-to. Pair them with a sweater or knit that feels sharp but laid back.
Stylist Mathew adds, “Layering is always a great way to complete any outfit as the holidays roll around.” He continues, “Style a plaid shacket, corduroy button-down or leather jacket over a plain tee.” Footwear matters here—switch your worn-out sneakers for a clean pair of white low-tops or leather-like boots. The goal is to keep it casual but polished enough that you can move seamlessly from a brewery to a friend’s living room.
“Layering is always a great way to complete any outfit as the holidays roll around. Style a plaid shacket, corduroy button-down or leather jacket over a plain tee.”
-Matthew, Stylist
Low-Key Holiday Celebrations
Not every holiday moment requires dressing up. From at-home celebrations to casual nights with friends, comfort and versatility take the lead.
A shacket (AKA a shirt jacket) layered over a tee or lightweight sweater strikes the perfect balance. Pair with jeans and sneakers or hybrid boots that feel rugged but refined. Keep accessories minimal—a knit beanie or sleek belt is enough to tie it together.
Looking for something even comfier? Stylist Mathew advises: “A fresh pair of joggers or sweatpants can easily be dressed up or down for special occasions at home. A quarter-zip sweater or crewneck is comfortable but so elevated.”
“A quarter-zip sweater or crewneck is comfortable but so elevated.”
-Matthew, Stylist
Get your closet holiday ready
Want to upgrade your holiday wardrobe while simultaneously skipping the shopping chaos? Take your style quiz, order a Fix and let your Stylist do the work for you. They’ll choose just-for-you pieces to save you time (and a trip to the mall). Keep what works, and return the rest—or get special discounts when you keep 5+ pieces. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
