The season always sneaks up on us, and every year we find ourselves looking for holiday outfits that feel festive but still comfortable enough to wear from morning coffee to evening dessert. This season, we’re leaning into rich colors, soft textures, and timeless pieces that can carry us through every kind of gathering — from a relaxed family dinner to a dressed-up night out. These looks feel special without trying too hard, and they’re exactly what we’ll be reaching for all season long.
Holiday Outfits To Recreate This Season
Family Dinner at Home
Wide-leg trousers instantly make any outfit feel put together, even when the vibe is casual. We love pairing them with a textured top like a plaid blouse or a knit with button details. The result feels easy but polished, perfect for hosting dinner or relaxing with family at home.
A Day of Holiday Shopping
A soft striped sweater layered under a long wool coat is our go-to for errands or gift shopping. It’s warm, comfortable, and has just the right amount of color. Add boots or sneakers, depending on how much walking you’re doing that day, and you’re set.
Lunch with Friends
A fair isle or patterned knit paired with classic trousers is the kind of outfit that feels cheerful but not over the top. We love this look for a cozy lunch date or afternoon coffee catch-up — it’s festive in the most subtle way.
Tree Trimming
Corduroy pants are a forever favorite for this time of year. They’re soft, flattering, and add a touch of nostalgia. Pair them with a fair isle cardigan and your favorite flats for a night of decorating the tree or wrapping gifts by the fire.
Winter Gathering
There’s something about mixing cozy textures with a touch of romance that feels perfect for the season. We love how the fair isle sweater balances beautifully with the flowy tulle skirt. It’s a look that transitions seamlessly from daytime get-togethers to evening celebrations, especially when paired with a classic bag and simple heels.
Holiday Luncheon
Floral prints can feel right at home in winter when they’re done in deep, moody tones. We love pairing this floral sweater with black trousers and a berry coat for a pulled-together look that’s perfect for a holiday brunch or casual party.
Thanksgiving Day
Comfort meets polish with a printed mini dress and tall boots. This outfit looks great in family photos but still lets you relax and enjoy your meal. Add a few gold accessories and you’re ready for a day full of food and laughter.
Date Night
There’s something about chocolate brown that feels so sophisticated for the holidays. A sequin top and sleek midi skirt create a little shimmer without being too much. We’d wear this for a dinner out or a festive evening gathering.
Festive Get-Together
Printed mini dresses are always a win for casual gatherings. This one, with its mix of browns and creams, feels playful yet refined. Style it with heels or boots depending on the vibe, and you’re good to go from day to night.
For Every Other Occasion
When in doubt, neutrals always work. Black feels timeless and effortless, perfect for everything from school concerts to holiday travel. It’s simple, classic, and always in style.
No matter what your holiday season looks like, the best outfits are the ones that make you feel like yourself. Whether you’re staying in, going out, or doing a little of both, we hope these looks inspire you to dress in a way that feels special but still easy. After all, the holidays are meant to be enjoyed, and that includes what we wear. For more fall looks, check out our 15 Fall Outfits Blog Post!
Stay stylish,
Tiffany & Tegan
