For many, the holidays usher in a special time of year filled with celebrations and with it, the stress of having to pick out the best gift ideas and putting together perfect casual holiday outfits for every occasion. And while this year’s celebrations will be different as we continue to practice social-distancing and embrace face mask trends in favor of large holiday gatherings, that doesn’t mean you can’t dress up. And 2020 is the perfect time to strike the perfect balance between cozy and chic. Not convinced? Proof lies ahead.
WHO: Fia. WHAT: Hope Macaulay Bella Colossal Knit Jacket ($233). WEAR: Oversize cardigan, tank, and jeans. Since it’s a holiday season like no other, comfort is the top priority. But if you’re still feeling the need to get a little dressed up, then we recommend slipping into a pair of jeans and an oversize statement cardigan. It’s the fashion girl’s version of an ugly sweater, but way cuter.
We also love this Mango Multi-Color Knit Cardigan ($80).
WHO: Stella Adewunmi. WHAT: Lack of Color Carlo Rancher Wool Fedora Hat ($129); Zara Minimalist Sweatshirt ($36) and sweats; Leatherology Meadow Double Zip Camera Bag ($190). WEAR: Sweatpant set styled with a hat, coat, chains, and heels. Let Stella Adewunmi’s on-point outfit be proof that you can dress up your beloved sweats this Holiday season. Just accessorize them to the max and you’ve got a look that’s not only making the most of your COVID-wardrobe but also gives you an opportunity to bust out some of the things collecting dust in the back of your closet.
Don’t forget to finish off the look with heels. We recommend Sarah Flint’s Perfect Pump 100 ($355).
WHO: Georgette N. WHAT: Eloquii Menswear Vegan Leather Blazer ($150); Ralph Lauren Pleated Metallic Midi Skirt ($205). WEAR: Metallic pleated skirt, T-shirt, and blazer. Just because this holiday season won’t be filled with as many opportunities to dress up, that doesn’t mean you can’t get use out of your metallic pieces. You can dress down a metallic or sequin piece by styling it with simple wardrobe staple pieces (i.e., a T-shirt or blazer) for a holiday outfit idea that strikes the perfect balance between casual and festive.
Prefer sequins over pleated pieces? We recommend Eloquii’s Sequin Skirt with Side Slits ($90).
WHO: Thamarr. WHAT: Anthropologie Monique Sweater Set ($148); Steve Madden Loft Heeled Sandal ($25); Catmicoo Cloud Crossbody Bag ($36). WEAR: Sweaterdress with sandals. The easiest way to walk the fine line between casual and festive this holiday season is by relying on knitwear. Specifically, don’t be afraid to opt for a sweater dress or matching set as they can be styled up or down and are far more comfortable than one might expect.
Already have the perfect sweater dress? Finish off your look with Mansur Gavriel’s Mini Cloud Clutch ($495).
WHO: Michelle Driscoll. WHAT: House of Sunny Peggy Cardi ($105); Holiday The Label Kokomo Pant ($165). WEAR: Statement sweater and statement jeans. I’ll repeat it: Festive clothing doesn’t have to include traditional pieces with sequins or velvet details!. Pairing a fun statement sweater with mismatched pants has the same fun energy as a dressed-up holiday look sans the predictable frills.
Pair these pants with this Zara Faux Fur Trim Knit Cardigan ($70).
WHO: Nitsan Raiter. WHAT: Storets Nina Curve Hem Cropped Shirt ($65); Sunday Best Olive Skirt ($98); Prada Nylon and Saffiano Leather Mini Bag ($985); Dr. Martens Smooth Leather Oxford Shoes ($120). WEAR: Button-up top, jumper, pleated miniskirt, and oxfords. One of the best things about fashion is dressing up for those annual milestones, like back-to-school or the holidays. And while this year’s special moments have changed, you can opt for a look that melds the two together. Pleated skirts are not only trendy but they’ll also give you maximum festive vibes.
On a tight budget? You may like this Topshop Flippy Faux Leather Pleat Miniskirt ($50).
WHO: Bella Cohen. WHAT: & Other Stories Cut-Out Collared Sweater in Khaki ($90). WEAR: Cutout sweater with pants. Unless you’ve been off the grid, you’re probably well versed in the fact that cutout clothing is one of the biggest trends this fall. Iterations of cutout knitwear have been everywhere lately, which makes it the perfect piece to shop for the holiday season. Cutout knitwear is not only on-trend, but it’s also something you can wear for celebratory events and everyday occasions.
WHO: Chrystelle Eriksberger . WHAT: Baum und Pferdgarten Daphnie Coat ($419); Ducie London Kendall Black Boots ($400). WEAR: Statement coat, Chelsea boots. Consider this a public service announcement: a holiday outfit does not need to be overly polished, sparkly, or themed to be festive. Try wearing a fun statement coat and your favorite pair of Chelsea boots for a look that’s both practical and still lively.
Pair this coat with these Free People Ash Magma Lugged Chelsea Boots ($250).
WHO: Javi. WHAT: Fashionnova trench coatWEAR: Turtleneck, jeans, and a trench coat. Striking a balance between casual and just polished enough to be around the family can feel like fine art, but it’s not impossible. Just slip into an old-reliable turtleneck, jeans, and a statement trench coat. While this is by no means an original holiday outfit idea, it’s definitely one you can count on to work no matter who shows up.
Already have a trusted turtleneck? Pair it with BlankNYC’s Faux Snakeskin Trench Coat ($118).
WHO: Celeste. WHAT: Monki Grace Plaid Print Blazer ($79); Alexander Wang Turtleneck; Maria Black Mio Chain Necklace ($160). WEAR: Turtleneck, sweatpants, blazer, baseball cap, and chains. If the thought of slipping into denim makes you cringe after nearly a year of working from home, we’re here to tell you that you really can make those sweatpants festive. Just pair them with a colorful blazer, turtleneck, and some jewelry, and you’ve got a look that can make you feel the most dressed-up you’ve felt in months—even if you’re only heading to your living room.
Still, searching for the perfect sweatpants? You may like Michael Star’s Madison Pull-On Pant ($138).
WHO: Sheryl Luke. WHAT: Zara Patch Pocket Knit Jacket ($50); Amina Muaddi heels. WEAR: Cardigan, slip dress, heels. If, despite everything, you can’t possibly picture yourself wearing sweatpants this holiday season, then go for a more dressed-up look that won’t be too fancy for your socially distanced celebrations. Just throw on a silk slip dress and cardigan (shoes are optional at home).
Pair with this Zara Patch Pocket Knit Jacket ($50).
WHO: Sophie . WHAT: ASOS Pink Cropped Pants ($48). WEAR: Contrasting bright-colored sweater and pants. The best way to get into the holiday spirit this season is to opt for bright hues. Pair two of your favorite bold colors together in the form of pants and a sweater, and you’ve got a look that will brighten up winter days to come.
We also love this affordable similar Mango Embossed Contrasting Knit Sweater ($60).
WHO: Monikh Dale. WHAT: Tove Ceres Tie-Detailed Gathered Cotton-Poplin Midi Dress ($520). WEAR: Colorful midi dress. Not a fan of the idea of styling two bold hues together? How about just one? After all, Who What Wear UK contributor Monikh Dale makes a serious case for lounging at home during the holidays in a colorful dress. Remember, you can re-create this look in any fabric or cut just so long as you wear a color that brings you joy.
Searching for a heavier fabric? We recommend this She Made Me Lolita Crochet Dress ($287).
WHO: Sophia . WHAT: Steele Alora Cardigan ($219) and Cassian Skirt ($199); New Balance sneakers. WEAR: Knit skirt set and sneakers. Frankly, it doesn’t get any cozier or down-right festive than knitwear during the holiday season. If you’re looking for a casual outfit idea, we highly recommend opting for a matching knitwear skirt set in a neutral hue. We promise it won’t disappoint.
Pair with the matching Enza Costa Sweater Rib Pencil Skirt ($145).
WHO: Coco Bassey. WHAT: Lack of Color Wave Bucket Hat ($89); Victor Glemaud Knit Top and Shorts; Prada Monolith Patent Leather Lace-Up Shoes ($950). WEAR: Knit short set/romper with a bucket hat and loafers. Love the idea of matching knitwear, but not a fan of skirts? If you’re reveling in warmer climates, try this casual holiday outfit idea in either short or romper form. The best thing about knitwear is that many cuts and styles, making it the perfect contender for every celebration.
Goes with the Zara Wool Blend Knit Top ($36) and Wool Blend Coat ($119).
WHO: Lydia. WHAT: Mumshandmade Oversized V-Neck Sweater ($262); Bared Footwear Sandals; Mashu Iris Creme Bag ($375). WEAR: Oversize sweater and slip skirt. Still not sold on knitwear sets? You can achieve the same comfortable vibe without actually wearing head-to-toe knits. Just look for an oversize sweater (in any color) and pair it with a matching slip skirt and accessories for a lighter monochrome feel that’s perfect for any festive occasion.
Pair with Max Mara’s Leisure Washed-Satin Midi Skirt ($240).
WHO: Tamira Laboy. WHAT: Gucci bag; Celine boots. WEAR: Blazer, T-shirt, jeans, ankle boots. Without fail, blazers are the wardrobe staple you can count on for any occasion—including the holidays. If you’ve spent the past few months not dressing up, then putting on a pair of jeans and a blazer can strike the perfect balance between perfectly polished and just casual enough.
Need a great boot to pair with these jeans? We recommend these Sam Edelman Samantha Ankle Booties ($160).
WHO: Nicole Ocran. WHAT: Sézane T-shirt; Simply Be velvet blazer and pants. WEAR: T-shirt and a velvet suit. If you’ve made it this far and you’re still not loving any of these casual holiday outfit ideas, may we suggest getting a little fancier? While epic office parties won’t be a thing in 2020, that doesn’t mean you can’t celebrate in a chic velvet party suit. Just dress it down with a T-shirt and flats for a festive fuss-free look.
Prefer black? You may like this Topshop Idol Black Velvet Suit Blazer With Peak Lapels ($125).
WHO: Maren Schia. WHAT: Bik Bok. WEAR: Satin top, jeans, and heels. Yearning for the nights you used to go all out, but know that you want to keep it a bit more casual this holiday season? Why not slip into a satin top, jeans, and a fun statement heel? Sure, you’re only going to your living room, but you will be the chicest woman there.
Pair these sandals with this Nanushka Cropped Twist-Front Satin Top ($415).
WHO: Erika Boldrin. WHAT: Frankie Shop Vanessa Cotton-Jersey Sweatshirt ($159) and Vanessa Cotton Trackpants ($152). WEAR: Matching jumper and sweatpants accessorized with chains. If you haven’t noticed yet, creating the perfect casual outfit idea for the holidays takes a bit of effort. And if you’re still at a loss for what to wear this season, just remember that whether you choose to walk around in your heels in your bedroom or layer on jewelry over your sweats, the key to creating the perfect look is one you feel comfortable in. The rest lies in how you accessorize.
