How To Dress Comfy For Thanksgiving Without Looking Like A Slob

While your mind may immediately go to your favorite matching sweatsuit, I’m here to help you reconsider. A cute and feminine loungewear set is great to have on hand (in fact, that’s why we launched our very own Evie collection), especially while traveling. However, when it comes to holidays and special events like Thanksgiving dinner, putting your best foot forward is essential (and respectful to whoever is hosting). Showing up with disheveled hair in a scrunchie while wearing pajama bottoms and a stained t-shirt isn’t only unacceptable, it’s straight-up rude. Let’s add a little class back to the holiday season this year, shall we?

You may be surrounded by your sisters, in-laws, or entire extended family, or it might just be you and your husband at home this year. Whether your plans are to indulge in your mom’s famous pumpkin pie and keep up with the Kelces on your flatscreen, or you’ve got reservations at the most iconic place downtown with your cousins and can’t wait to shop all the Black Friday sales post-meal, why dress like it’s any ordinary day when you can embrace your feminine energy and romanticize the moment? 

There’s a trick to staying comfortable while also looking and feeling your most stylish, though. Think about some of the coziest pieces in your fall/winter wardrobe. They likely extend far beyond your worn-in college hoodie. You don’t need to wear your tightest bodycon dress or cropped balloon-sleeve blouse to feel put-together; you just need to get creative with the fabrics you’re choosing and how you layer each piece to create a cohesive and ultra-chic outfit. Let’s get into six tips for dressing comfy this Thanksgiving without looking like a slob – with shopping recommendations to match, of course!  

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Embrace Silk

Silk midi skirts are the “it” item to have – not only this year, but every fall and winter. I’d even argue that they’re an appropriate closet staple year-round if styled in the right way. However, when it comes to an easy, comfortable, and chic holiday look, the silk (or satin) skirt is the most straightforward way to go. Depending on how fancy the setting is, you can dress this piece up or down with items like a claw clip for your hair, gold hoop earrings, or even kitten heels. Order one size bigger than normal if you want your skirt to lay loosely above your waist for the most comfortable fit.

Shop: Elevated Satin Column Maxi Skirt (Cream) $80 | Gwyneth Slip Skirt (Camel) $90 | Satin Midi Slip Skirt (Black) $40

Invest in Cashmere

Can you imagine anything cozier? A cashmere sweater is one way to look and feel like a dream on Thanksgiving. While cashmere often comes with a hefty price tag, there are brands like Quince that make it much more affordable to invest in this fall/winter staple. Pair your sweater with straight-leg trousers and a blazer or belt, or find the perfect cashmere sweater dress for the comfiest fit.

Shop: Mongolian Cashmere Crewneck Sweater (Black) $50 | Caro Oversized Lightweight Cashmere Sweater (Ivory) $150 | Mongolian Cashmere Turtleneck Sweater (Brown) $80

Layer with an Oversized Knit

Ah, the quintessential cold-weather fashion staple. While we love this item, it can easily go from chic and effortless to slob-kabob in mere seconds if you’re not careful. Mainly due to unbalanced proportions (which we’ll address further down), layering with an oversized knit needs to be done strategically so you don’t get swallowed up and lose your feminine shape entirely. 

Personally, my favorite way to style this closet staple is with a mini skirt or dress. If the weather in your area is hot and cold, this is often the best solution to ensure you’re neither freezing nor sweating on the day. Mix one solid color (like a black or hunter green knit sweater) with one pattern like fall florals or winter houndstooth in a skirt for a statement-making look. Or go monochromatic and girly with a hair bow to match your sweetest oversized cardigan.

Alternatively, wearing a sleeveless sweater vest over a white button up dress is another timeless option perfect for the holidays. 

Shop: Driftwood Cable Polo (Green) $168 | LA Hearts Rory Cable Knit Oversized Sweater (Cream) $50 | Sweater Vest and Shirt Combo Dress (Tan) $32

Tres Chic in Trousers

Now, if you feel like wearing jeans on Thanksgiving while you’re trying to indulge in your favorite home cooked meal of the year isn’t realistic, then let’s look at an alternate option. We have the French girlies to thank for making this traditional menswear staple effortlessly feminine and elevated by pairing them with sleeveless sweaters, chic belts, and pointed-toe heels (which you can certainly leave by the door if you wish). 

Shop: Sculpted Straight Pant (Black) $45 | High Rise Pleated Wide-Leg Trousers (Camel) $80 | The Way-High Drape Pant (Cream) $128

Elevate Your Monochromatic Basics 

Maybe trousers aren’t your thing either, though. In that case, let’s work with what we’ve got on hand. A nice pair of black leggings can do wonders if you’re not immediately grabbing the largest crewneck in your closet to pair them with. Arguably among the most comfortable on this list, you’d be surprised how chic leggings can look when you give them the proper styling attention. 

Even if what you’re most comfortable in is your worn-in black jeans and matching black sweater, you can elevate it for a holiday setting simply by adding a chic coat and bold earrings. 

Shop: Girlfriend Jean (Black) $35 | High Waisted Jersey Ankle Leggings (Black) $15 | Crew Hoop Set $98

Balance Your Proportions

To round out these tips, we have arrived at the golden rule that applies to all of them. Balancing your proportions is an essential step in styling a feminine and flattering outfit and should not be taken lightly. You can own the most expensive cashmere sweater, the most coveted trousers every influencer swears by, and that designer handbag that costs more than an SUV, but if your proportions are off, you’re bound to look a bit sloppy.

Rather than going full oversized (which often comes off as androgynous) or skin-tight from head to toe (which gives the impression you’re trying too hard), make sure that what you’re wearing is ideal for showing off your feminine shape in an elevated way. If you’re grabbing that oversized knit on top, show off your legs with a mini skirt or dress underneath, or wear fitted pants on bottom. Alternatively, if you’re going with a tighter top, opt for loose-fitting trousers or a flowy midi or maxi skirt on the bottom. 

Of course, there are some exceptions to the rule and ways to skirt around it, like doing a half-tuck with your chunky sweater or adding the perfect belt to define your waist, but in general, keep the one-to-one ratio in mind to make getting dressed a breeze. 

Closing Thoughts

Heading home for the holidays doesn’t mean we should let our inhibitions go and start dressing like Post Malone just because we’re surrounded by those we’re most comfortable with. Imagine yourself in your favorite holiday romcom (it’s Cameron Diaz’s The Holiday wardrobe for me) and romanticize this season by dressing your best while remaining comfortable and cozy. It can be as simple as swapping out your oversized hoodie for a cashmere sweater and layering it with black leggings and a matching black wool coat for the occasion! 

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