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Finding the perfect outfit for the crazy fall and holiday seasons should be fun, not a total headache. To help you out, we’ve put together a list of trendy and timeless looks that will go perfectly with everything on your agenda. Whether you’re heading to a casual Friendsgiving dinner or getting dressed up for the big family celebration in December, we’ve got you covered.
We’re not just guessing either: our research is backed by data from Google Trends, which shows that everyone is getting off to a flying start with their Christmas shopping this fall. We’ve seen a spike in searches for terms like “holiday dresses 2025” since the end of summer, proving that people are planning their looks well in advance. Plus, the search term “festive fashion” will reach its peak in early December, so you know everyone’s year-end attire is a major focus right now.
Friendship
For this relaxed gathering, aim for looks that combine elevated comfort with effortless style.
Classic comfort: Choose a sleek, modern version of the fitted trousers with the Corduroy utility trousers with darted barrel legs from Madewel. Can be worn both chic and casual with a cardigan like this Scattered jeweled oversized cardigan with VT neckline from Bloomingdales.
Cozy chic alternative: For a more relaxed, yet elevated feel, opt for a monochrome skirt in a rich cocoa brown color like this one Turtleneck and satin slip dress from Nordstrom combined with statement loafers or ankle boots with a low heel.
Thanksgiving
Keep comfort and style in mind during this long day of fun, partying and probably football.
The elevated midi dress: Choose a flowy, autumn-colored midi dress in a forgiving silhouette and soft fabric like this one Midi shirt dress with belt by Ann Taylor. This look is comfortable for eating, but instantly polished for photos.
Casual chic: A stylish, oversized sweater like this beautiful toffee-colored one Raised Alpaca crew neck by Naadam combined with denim in a dark wash is perfect for a casual meeting. Complete the look with fashionable flats or block heels.
Working holiday party
Try to balance professionalism and festivity.
Sequins and structure: A black or jewel-toned mini dress with structured tailoring and a touch of tasteful glitter, such as metallic thread or subtle sequins on it Black one sleeve sequin mini dress by Mac Duggal. Let the dress do the talking and keep the accessories minimal and sleek.
Modern jumpsuit: A wide-leg jumpsuit in a rich fabric is a sophisticated alternative to a dress like this Nova Cape Jumpsuit by Alice + Olivia. Add personality to the classic black silhouette with a statement earring or clutch.
Family holiday party
Go for traditional elegance with a festive flair.
Classic cocktail dress: You can’t go wrong with a classic cocktail dress. Look for fabrics that feel luxurious, like this velvet Camille velvet dress from the Reformation. A deep, moody red with gold accessories is trendy and appropriate for the season.
Revival of the Power Suit: Embrace the trend with a velvet or brocade suit in an unexpected striking color like this Silas single-breasted satin blazer and matching Nessi satin wide leg pants by Alice + Olivia. Wear a silk camisole underneath and complete the look with glittering pumps. It’s a strong look that stands out without being overly flashy.
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