MomSkoop
The holiday season is all about celebrating with the people you love, but that doesn’t mean you need to stress over what to wear.
Finding outfits that feel festive yet comfortable can make your celebrations so much more enjoyable.
Whether you’re heading to a family gathering or meeting friends for hot cocoa, these casual holiday looks will help you feel cute and confident without any fuss.
1. Cozy Sweater Dress with Ankle Boots
Nothing says effortless holiday style quite like a sweater dress that hugs you in all the right ways.
Pick one in a festive color like cranberry, forest green, or classic cream, and you’re already halfway to looking amazing.
Ankle boots add just enough edge to keep things interesting without making you feel overdressed.
Throw on some simple jewelry—maybe a delicate necklace or small hoops—and you’re ready to go.
This combo works for pretty much any casual holiday event, from brunch with family to evening get-togethers.
Plus, you’ll stay warm and comfortable all day long, which is really what the holidays are about.
2. Plaid Shirt with Dark Jeans and Sneakers
Ever wonder why plaid never goes out of style during the holidays?
It’s because flannel shirts in festive patterns instantly give off those cozy winter vibes we all crave.
Pair your favorite plaid button-up with dark-wash jeans for a look that’s both polished and relaxed.
White or black sneakers keep things casual and comfortable, especially if you’re doing lots of walking or standing.
You can leave the shirt unbuttoned over a plain tee for a laid-back vibe, or tuck it in for something a bit more put-together.
Either way, this outfit screams holiday cheer without trying too hard.
3. Turtleneck and Midi Skirt Combo
Want to feel fancy without the fuss of a full dress?
A turtleneck paired with a flowy midi skirt strikes that sweet spot between dressy and comfortable.
Choose a solid-colored turtleneck—black, cream, or even a rich jewel tone—and match it with a patterned or velvet skirt.
Add some tights if it’s chilly outside, and slip into flats or low heels depending on your plans.
This look is sophisticated enough for a nice dinner but still easy to move around in.
You’ll look like you put thought into your outfit, even though it took you less than five minutes to throw together.
4. Oversized Cardigan with Leggings and Booties
Sometimes you just want to feel like you’re wearing a blanket, and that’s totally okay.
An oversized cardigan gives you all the warmth and coziness you need while still looking stylish.
Layer it over a simple tee or tank, then add your favorite leggings for maximum comfort.
Booties elevate the whole look so you don’t feel too casual, and they’re way easier to walk in than heels.
Choose neutral tones like beige, gray, or camel for a chic vibe, or go bold with a deep red or green.
This outfit is ideal for low-key holiday hangouts where comfort is your top priority.
5. Graphic Holiday Tee with Mom Jeans
Feeling playful this holiday season?
A fun graphic tee with a festive print can show off your personality while keeping things super casual.
Look for shirts with cute sayings, reindeer, snowflakes, or even funny holiday puns that make people smile.
Pair it with high-waisted mom jeans for a trendy yet relaxed silhouette that flatters just about everyone.
Sneakers are the obvious footwear choice here, keeping the whole vibe youthful and carefree.
This look is awesome for casual parties, shopping trips, or just hanging out with friends during the festive season.
Plus, you’ll definitely get compliments on your shirt!
6. Velvet Pants with a Simple Blouse
Velvet pants might sound fancy, but they’re surprisingly comfortable and easy to style.
The soft texture feels luxurious while still being totally wearable for everyday holiday events.
Go for classic holiday colors like deep green, navy, or burgundy to capture that festive spirit.
Pair them with a simple tucked-in blouse—nothing too complicated—and you’ve got an outfit that looks thoughtful and chic.
Flats or low block heels work great here, keeping you comfortable if you’re on your feet a lot.
This combination is dressy enough for nicer gatherings but relaxed enough that you won’t feel stuffy or overdone.
7. Denim Jacket Over a Holiday Dress
Here’s a fun fact: denim jackets make almost any outfit feel more approachable and less formal.
If you have a cute holiday dress but don’t want to look too dressed up, just throw a denim jacket over it.
This instantly transforms your look from fancy to friendly, making it ideal for casual daytime events.
Choose a dress in a festive print or solid holiday color, then let the denim jacket add that cool, laid-back touch.
Ankle boots or even sneakers work beautifully with this pairing, depending on how casual you want to go.
It’s one of those outfits that feels effortless but still gets you plenty of compliments.
8. Monochrome Loungewear Set Styled Up
Who says loungewear can’t be holiday-appropriate?
A matching sweatshirt and jogger set in a neutral tone looks polished and intentional, not sloppy.
The key is choosing a set that fits well and looks cohesive, not just any random sweats from your drawer.
Add a pair of clean sneakers and some simple accessories like hoops or a baseball cap to complete the look.
This outfit is perfect for relaxed holiday mornings, casual get-togethers, or even traveling to visit family.
You’ll be ridiculously comfortable while still looking like you actually tried, which is the ultimate holiday win in our book.
9. Striped Turtleneck with Corduroy Pants
Stripes and corduroy together create a vintage-inspired vibe that feels both nostalgic and fresh.
A striped turtleneck adds visual interest without being too bold or flashy, making it easy to style.
Corduroy pants bring texture and warmth, plus they’re having a major fashion moment right now.
Stick with earthy tones like tan, brown, or olive for the pants to keep things grounded and wearable.
Sneakers or loafers are your best bet for footwear, keeping the overall aesthetic casual and approachable.
This combo works great for coffee dates, shopping trips, or any laid-back holiday activity where you want to look cute without overthinking it.
10. Knit Co-ord Set with Statement Coat
Matching knit sets are having a huge moment, and for good reason—they make getting dressed ridiculously easy.
Choose a coordinating sweater and pants combo in a soft, cozy knit fabric that feels like a warm hug.
Layer a statement coat over the top to add drama and keep you warm when you’re outside.
Go for a coat in a bold color or classic neutral, depending on your personal style and mood.
This outfit looks incredibly put-together even though it requires minimal effort or thought.
It’s ideal for holiday outings where you want to look polished but still feel relaxed and comfortable throughout the day.