Hanukkah may be eight days and Christmas may be one, but anyone who’s fully attuned to this time of year knows that the holiday season extends over a month. The weeks between Thanksgiving and New Year’s Eve are filled with numerous parties, religious events, and festive traditions. Translation? You’ll be in need of a slew of stylish, yet event-appropriate, ensembles. But when you’re in the midst of lighting menorahs, shopping for the ultimate kitschy sweater, and finding the perfect Christmas tree, nailing down one (let alone 10) outfit is no easy feat. Allow us to check one thing off your never-ending holiday checklist with these fool-proof ensembles that will last you all season long.
1. Elevated loungewear for holiday movie binge-watching
So little time, so much to do. While there are some great holiday flicks out there — Home Alone, Love Actually, It’s a Wonderful Life — you only have a few weeks to watch them all. For any festive film fanatic, that obviously means coordinating a binge watching session with your nearest and dearest. With a bottle of wine, tins of holiday cookies, and a never-ending stream of movies at your disposal, we couldn’t think of a better way to spend a night (or two). And thanks to the recent boom in athleisure apparel, dressing for this occasion is fashion-forward and a no brainer. Equal parts cozy and stylish, a pair of luxe track pants is perfect for this lazy event. The fabric is usually insulting and soft, plus the forgiving elastic band will make digesting all that food and lounging on your sofa much more comfortable. To give these pants a proper, yet still laid back, twist, add an ironed chambray and a pair of slick, slip-on sneakers.
2. Keep it casual while hanging with the buddies
Don’t be fooled by the copious invitations to formal holiday dinners and that dreaded corporate soiree: There is no better time than the holidays to showcase your best knits and casual wear. Whether you’re grabbing a peppermint mocha latte — we’re not judging; they’re delicious — with your best bro or playing a game of drunken dreidel with a big group of friends, dare to keep you outfit casual this year. Our pick? Pairing a bright flannel with your treasured dark-washed jeans and white sneakers. For that extra holiday flair, opt for a plaid button-down in a merry hue — green, blue, or red are great options.
3. Cozy chic while decorating your house
Decking the halls (or your studio apartment) with boughs of holly does sound like a jolly happening, but anyone who has fully holiday-fied their homes knows that decorating is hard work. You need to perfect position all the characters in your Nativity set, confirm all trinkets are still inside your advent calendar, and hang a slew of wreaths all while simultaneously making sure your “Ultimate Holiday 2015 Playlist” is the perfect blend of spiritual, traditional, and millennial. Since things can get a little sweaty, especially while you’re fastening that pine tree into that overly-technical stand, our advice is to toss on a grandfather-inspired cardigan over a plain white T-shirt. Give this simple ensemble a festive edge by selecting a sweater in a fun pattern or color — we love the idea of sporting a country-esque fair isle while adorning your Christmas tree. Since comfort is key, top off this look with a pair of slightly distressed jeans and your trusty leather loafers.
4. The typical tacky holiday sweater
What would a holiday outfit guide be without briefly mentioning the ubiquitous, overly-zesty holiday sweater? Though Time.com credits the dawn of cheesy jumpers to the likes of Bill Cosby and Chevy Chase’s National Lampoon’s Christmas Vacation, we would like to think that they’ve always been around because, quite frankly, we can’t picture anyone getting through a holiday season without donning one. But the struggle emerges when trying to figure out how to make your ugly pull-over stylish. Truthfully, the whole premise of this garment is looking a little kitschy, so focus on comfort over fashion. Whether adorned with sequined “Star of David” incarnations or a giant Rudolph the Red-Nosed Reindeer, style these with a fitted pair of black or dark-washed jeans. While your sneakers will be a great addition to this outfit, your rugged snow boots will add a wintry touch to the look.
5. Look like a modern Casanova for date night
For many, the holidays are basically synonymous with romance. We mean, haven’t you watched Love Actually or any sappy Christmas movies where the two lovers always end up together and smooching behind a frosted window? Regardless of your opinion on sappiness, now is a better time than any (excluding Valentine’s Day, of course) to show your beau just how much you care. Whether embarking on a cozy horse and carriage ride or getting your inner foodie on at an upscale restaurant, allow your mushy tendencies to take the reigns. However, that also means wearing an ensemble that would also work for a leading man in a rom-com. The secret to looking mistletoe-ready? Throwing on some cuddle-friendly gear, which can easily translate as a fuzzy sweater and dreamy wool trousers. For a finishing touch that will completely channel your inner Casanova, throw on a crispy pair of brown leather lace-up shoes.
6. Walking (warmly) in a winter wonderland
Though this season is the best time of year to be snuggled up binge-watching your favorite show on Netflix, you find yourself out in the brisk chill a little too often. The hypnotizing holiday windows and marshmallow-like snow make it impossible to stay out of the cold for too long; however, staying warm is priority. Unless you’re hoping to resemble the Michelin man, lose the unflattering puffer jacket. A lighter puffer jacket underneath a luxe top coat is a effortlessly chic, and more flattering, way to keep warm. Luckily, this topper layering technique can be matched with anything from sweats to a more polished suit — just don’t forget to sport your scarf, hat, and gloves if the climate requires. While your sneakers or brogues could both easily work with this outfit, it’s important to keep your traction-clad snow boots on the footwear back-burner. No matter what you’re wearing, slipping on black ice is never chic.
7. Loosen up for the office holiday party
If the holidays are collectively known as the most wonderful time of the year, let us call the annual office holiday party the most peculiar time of the year. Perhaps your boss winds up making a long speech that offends a few of your co-workers or maybe you spot the receptionist and the HR manager getting a little too close, but one thing’s for sure: This fête is both awkward and mandatory. But what to wear? Most likely, your holiday party will take place right after office hours, which means you’ll be sporting your work wear to the soiree: dress shirt, tie, trousers, and your wing-tip shoes. While this ensemble is not reinventing the wheel for party apparel, giving your office gear an off duty twist is easy with a few quick tweaks. Ditch the tie (save those holiday-printed ones for your awkward boss) and cuff links and let loose by pushing your sleeves up to your elbows and unhinging the first button on your dress shirt. While we don’t condone having too many beers at the party, you should at least look like you’re relaxed and having a good time.
8. Luxe pajamas for Christmas morning
On a day to day basis, most of us couldn’t care less about what we wear to sleep. After all, besides your bed buddy, roommate, and/or kids, who’s going to see your PJs? On Christmas morning, the answer is everyone. Your bed buddy, kids, mom, dad, grandma, grandpa, aunts, uncles, cousins — shall we go on? And what’s worse, is that you know your mom will be collecting Kodak moments with her camera (or, if she’s tech-savvy, smartphone). This all means one thing: You need a good pair of pajamas, stat. Whether solid or adorned with a funky pattern, a matching pair of silky pajamas will add some much-needed glamour to your Christmas morning. Coupled with some shearling-lined slippers, your morning look will be both classic and warm. If you’re not looking to splurge on lavish jammies, pull that fluffy robe out from hiding. After all, that terrycloth draping will act as lush layer to add onto your sleep suit while masking your archaic college sweats you normally wear.
9. Win over your extended family with a smart outfit
Sure, they’re your family, but enduring a three-course meal with your outspoken grandpa, judgmental aunt, and those in-laws you don’t even like can be a struggle. Between the soup and the glorious Christmas ham, you know that they’ll grill you on everything: work, money, dating, and views on Donald Trump. During this event, allow your outfit to be the sartorial mic drop — you may be single and hating your job, but at least you look suave. To create an ensemble that’s a step above your competitive cousin’s, ditch the typical dress shirt and opt for a cozy turtleneck sweater in a versatile neutral and style it with a fitted blazer. Add a pair of easy wool trousers along with your trusty brogues and you’ll be the definition of smart and sophisticated at the dinner table.
10. Ring in the New Year with fancy formalwear
Whether you’re counting down the seconds until 2016 at a relaxed house party or crowded club, there’s something about New Year’s that requires formal attire. Your female counterparts have their go-to outfits — anything sparkly and short — but what about you? After all, you’re not going to welcome a new year looking like a human disco ball. Instead, opt for casual take on a luxe suit. With your matching sports jacket and trousers as a base, dressing party-ready is as easy as adding a white dress shirt with the top two buttons undone. Those leather shoes that you save for important occasions are a perfect finishing touch — just don’t forget to add some much-needed depth to your ensemble by accessorizing your outfit with a contrasting pair of shoes. For example, dark brown brogues would go perfectly with a dark gray or navy suit.
Follow Kelsey on Twitter @KMulvs