Huge thanks to Kohl’s for sponsoring this post

Getting dressed for the holidays can feel more stressful than it needs to be, between figuring out what’s “dressy enough,” wanting to feel festive, and still wanting to be comfortable. So, today I’ve got you covered with four holiday outfit ideas that are elevated and polished, whether it’s for a nice casual gathering, a holiday dinner, a concert, or a work event.

All of these pieces are from Kohl’s, which means they’re SUPER affordable while being stylish, easy to wear, and comfortable! I seriously find the best stuff at Kohl’s and cannot believe how comfortable some of the clothes are and how good the prices are. Plus, Kohl’s offers a good range of sizing options, including straight, petite, plus, and some tall pieces. You can also shop conveniently at Kohl’s with their curbside and in-store pickup!

And, right now you can take 20% off with code GOGET20 until 11/22!

Elevated Casual Holiday Outfit: Red Plaid Button-Up + Wide Leg Jeans + Red Mary Jane Shoes

A red plaid button up is classic for the holidays! It instantly makes you feel festive and adds a seasonal pop while still feeling casual and wearable. And this red plaid flannel button up is SO GOOD! It’s thick and warm, and it holds its structure to look polished, but it’s not stiff or stuffy-looking. It feels cozy and keeps you warm but looks really polished — and festive! And, it’s only $19.99!! Such a good piece to have in your closet, and so affordable! It comes in 22 colors, HERE. I’m wearing size S.

I paired it with wide leg jeans to create a fresh, modern holiday outfit. These jeans are only $22.39 and are pretty soft and lightweight to wear. Find them HERE. I’m wearing size 6.

If you don’t like wide leg jeans, you can totally wear this outfit with dark wash straight leg, bootcut, or flare jeans. If you’re looking for a great pair of comfortable straight leg jeans or a great pair of flare jeans, I’ll share some later in this post!

To pull the whole outfit together, I added red Mary Jane flats. Not only do they echo the festive vibe of the top, but the pop of red on your feet adds a playful, put-together finish. They’re comfortable with a rubber sole and cushioned footbed, and they add a fun twist on your outfit — so CUTE! They come in LOTS of colors. I also own them in Pewter! See them all HERE. I wear size 9.

This outfit would be perfect for a casual holiday party, dinner with friends, or even a festive day at work.

Elevated Casual Outfit: Cable Knit Sweater + Medium Wash Jeans + Red Mary Jane Flats

This outfit is giving festive, comfy, and casual—but cute! A white cable knit sweater is a timeless winter staple, and this one is SOOOO soft and COZY!! The cable knit texture adds that classic, wintry vibe, and you feel like you’re wrapped in a super cozy, comfy blanket of goodness. 😄 Comes in 6 colorways, HERE. I’m wearing size S.

This thick sweater pairs effortlessly with straight leg jeans. These jeans are thick and supportive but are also stretchy and comfortable! (If you’re familiar with my favorite pair of flare jeans by Lauren Conrad — shown below — these feel the same but in a straight leg cut.) They come in several washes, which you can see HERE. I wear size 6.

To finish it off, I added the same red Mary Jane flats from Outfit #1. They’re such a fun, festive touch that adds color and personality without needing to go overboard. Just a little pop of red goes a long way in making an outfit feel holiday-ready!

This is a great outfit for casual get-togethers, running errands with a little holiday flair, or just staying cozy while still looking cute.

Dressy Casual Holiday Outfit: Blouse + Dark Wash Flare Jeans + Pointed Toe Boots

When you want to look a little dressy but not over the top, go for dressy casual with a blouse, dark wash jeans, and pointed toe shoes. This outfit formula never fails!

This blouse is my go-to dressy top! I own it in three colorways now(!!), and it makes dressing up for ANY holiday event SUPER easy. The sleeves make an effortlessly elegant statement, and the fabric at the torso is thick and STRETCHY, so it’s COMFY but looks so, so CHIC. The best! I wore it to my mom’s 70th birthday party, to sing for a Christmas Eve service, to sing for Easter, and to a Christmas party. It’s my go-to blouse, and I mean it! Currently available in 4 colorways and ONLY $23.99 HERE!! I wear size S.

You can pair this blouse with anything, including trousers, faux leather pants, a skirt, or jeans, like I’m doing here. Dark wash denim automatically looks sharp, so you can always rely on it when dressing up. I’m wearing my trusty favorite flare jeans, which add a little drama and polish. These jeans are thick and structured but are STRETCHY and comfortable! They’re just $31.99 right now, which is a STEAL for how good they are! Find them HERE. I wear size 6.

I finished off the outfit with pointed toe boots — another dressy must-have in your wardrobe. This style with the pointed toe and the kitten heel is my go-to recommendation for dressy outfits. It INSTANTLY makes your outfit look refined, pulled together, and polished. Don’t be scared by the kitten heel. A low one is pretty easy to walk in! Grab these boots HERE to wear with every one of your dressy outfits this winter! I wear size 9.

This is a perfect outfit for a holiday concert, dinner party, or work event!

Dressy Outfit for the Holidays: Printed Blouse + Black Wide Leg Pants + Pointed Toe Boots

Need something dressier? Try this! The floral print top is both festive and refined. This colorway is a little sheer and has metallic threads that elevate and dress it up. SO PRETTY! 😍 It comes in several other colors that are great for everyday wear, too. See them HERE! I’m wearing size S.

I paired it with black wide leg pants for a cohesive, modern outfit. These pants drape beautifully and are dressy and polished, but they’re SO, SOOOOOO comfortable! The fabric is thick and STRETCHY, but they look elevated and sophisticated! Find them HERE. I’m wearing size 6.

Finish it off with pointed toe boots again. They peek out from under the wide legs and add the sharpness that wide leg pants need to look polished, not frumpy. I mean it — these boots make it EFFORTLESS to look chic and dressed up!

This would be perfect for a work party, a more formal holiday gathering, or even a festive night out where you want to feel a bit glam but not overdone.

Shop More Holiday Outfits — 20% Off

These are all SUCHHHHH GOOD PIECES for your holiday style needs! And they’re so dang affordable, especially while they’re 20% off! Grab some of them so that you’re ready for ANYWHERE your holidays take you. Remember to use code GOGET20 to get 20% off through 11/22!

And, here are even more pieces to check out for easy holiday outfits!

Looking for more gift ideas? Find all my gift guides and cross everyone off your list at the Gift Guides station!