7 Fabulous But Casual Holiday Outfits You Can Wear Now & Later

Casual Holiday Outfits

When it comes to holiday outfits, not every occasion calls for all the sparkle and glam. Sure, we love a great sequin dress, velvet top, and crystal embellished pumps…but quite often those pieces are relegated to the back of your closet once the holiday season passes, right? If you are looking for some casual yet festive outfits you can wear during the holidays and beyond, these looks are for you! We’ll share ways to style these pieces now and later so you can boost their fashion longevity. You might even find that you have similar pieces in your closet and can easily recreate these looks with items you already own.

For holiday tops (both casual and dressy!) that you can wear with your favorite jeans, you’ll want to check out this post next.

casual holiday outfits

casual holiday outfitsMini Dress & Tall Boots

Look #1) Mini Dress & Tall Boots

This pretty chiffon Paige dress is the epitome of a wear-now, wear-later piece. The geometric print has very subtle metallic flecks that add a little oomph for the holidays but not so much that you wouldn’t feel comfortable wearing it all winter and into spring. It has a flattering v-neck with an attached self-tie sash that you can style a few ways. This is one of those dresses that could be dressed up or down depending on the accessories and 3rd layer you choose (long cardigan, moto jacket, denim jacket, or blazer, etc.) It’s super versatile!

Erin styled the dress with a pair of beautiful brown boots by Schutz, but you could also wear the dress with booties or heels and even add a pair of tights for a little extra warmth. The boots have almost a 4” heel but they are surprisingly comfortable for heels. The shape of the shaft with the small dip in the front and back is really flattering on the leg. These are a pull-on style, sexy boot that runs true to size.

casual holiday outfits

casual holiday outfits blouse and jeansSilk Floral Blouse & Baggy Jeans | Casual Holiday Outfits

Look #2) Silk Floral Blouse & Baggy Jeans

Here’s another example of a festive top that has all the holiday hues like green, red, and burgundy, but you can wear it pretty much year-round. Since it’s silk, it’s very lightweight but the elevated fabric means you can dress it up with trousers or a skirt, or you can wear it casually with jeans and booties like Erin’s wearing it. You can leave the tie keyhole at the neck open or closed which changes the overall look of the blouse. It has the prettiest puff sleeves with elastic cuffs.

The jeans Erin is wearing are a baggy, cuffed style by Citizens of Humanity. Aren’t these SO cool? If you’ve been wanting to try the baggy jean trend, the cuffed hem adds a little extra edgy chicness and we love the juxtaposition of the jeans with the super feminine blouse. The cuff isn’t sewn in, so you have some styling options there too. On her feet, Erin is wearing a pair of white Schutz booties that she loves so much, she owns them in multiple colors. The pointed toe helps keep the line long and lean which is key when wearing baggier, wide-leg jeans. To dress this look up even more for the holidays you could add a blazer or some pretty embellished pumps.

Casual Holiday Outfits

casual winter holiday outfitsstars sweater

jeans and boots

Look #3) Cashmere Sweater & Jeans

This next look is definitely one of the most casual options. If the sweater looks familiar, it’s because Erin has owned and loved it for years!  It’s an Aqua cashmere sweater that’s soft, cozy, perfect for layering, and affordable. The star detail down the sleeves is modern and fun. It also comes in navy blue with bright red stars. You can wear this sweater with jeans, lounge pants, or joggers.

Erin layered a chic and sporty SAM. puffer vest with shearling trim over the sweater and there’s just something about the black and white details in both the sweater and vest that look so cool paired together. She’s also wearing a flattering pair of black, wide-leg Hudson jeans that are the perfect length for her to wear with flats or a low heel (Erin is 5’4” for reference). To keep things casual, she’s wearing a pair of La Canadienne leather booties with side buckles that have a side zip for easy on/off. The stars and shearling trim give this outfit some holiday flare, but you’ll wear both pieces way past December!

vegan leather holiday outfitFaux Leather Joggers

Look #4) Layered Sweater & Faux Leather Joggers

This next look would be so chic for a holiday party but the sweater and joggers can also be styled a bunch of different ways this winter. These faux leather cargo joggers by Generation Love are super edgy and on-trend. They have a comfy elastic waistband, cinched cuffs, and cargo pockets on the sides. These look even more luxe in person and the fit is lovely. They are a tiny bit long on Erin but if you’re petite, you can always cinch the elastic cuff up your leg a bit. You could style the joggers with a basic white tee and sneakers or a classic sweater and booties. They’re more versatile than you think!

Erin paired the joggers with a pre-layered sweater by Cinq a Sept. What a statement-making sweater with the tie cuffs and flattering rounded hem! Then the sweater will work for the office with trousers, or you can wear it more casually with jeans or leggings since the length is longer in the back.

On her feet, Erin’s wearing a pair of Michael Kors faux leather booties that she owns in both black and brown (because they are just that good!). They’re super sexy, unique, easy to style, and VERY comfy. The sock bootie silhouette means they’ll work with any pair of jeans, dresses, and skirts. To amp this look up for the holidays, add a red lip, a pair of sparkly earrings, and a black clutch.

Cable Knit Zip Sweater & Baggy Jeans | Casual Holiday Outfits

Look #5) Cable Knit Zip Sweater & Baggy Jeans

This gorgeous, off-white cable-knit sweater by Vince is casual, warm, and cozy. It has a drop shoulder and a collared neck that you can zip up all the way, partially, or leave completely unzipped depending on the look you’re going for and…how cold it is. It’s 100% wool so it will keep you extra warm. We love that it’s not too bulky so you can still wear it under your coats and jackets. Erin styled it with the same baggy light-wash jeans and white booties from look #2. This is one of those couch-to-curb, elevated sweaters that you’ll wear all day long! If you want to dress it up for the holidays, pair it with a leather or faux leather skirt, or a pair of pants or joggers. And then come January, you can also wear it with your favorite pair of lounge pants or sweats.

tops for Christmas

Blue Off-The-Shoulder Sweater

Look #6) Off-The-Shoulder Sweater & Jeans

Here’s another casual but also elevated outfit. This look will work for a holiday party, a night out with the girls, or a date night. The off-the-shoulder, cobalt blue ASTR The Label sweater adds a touch of sexy without being over the top. This is one of those colors that looks SO good on so many women. The one-shoulder neckline is super flattering, and the length is perfect. You can leave it untucked or half-tuck it because it’s not super long. This sweater sold out when we first featured it a couple of weeks ago, but we just found it fully stocked here. And, bonus…it’s under $100.

Now let’s talk about these jeans for a minute…the flattering factor is off the charts. If you are going to invest in one pair of versatile, slimming, dark wash jeans that you’ll wear for years, this is THE pair. Erin added some sparkly accessories to glam up this outfit for the holidays. But you could dress these pieces up or down for pretty much any occasion!

Red Jacket & Pants | Casual Holiday Outfits

Look #7) Red Jacket & Pants

Our last look is holiday-ready but can be worn for months to come…this red jacket and matching pants set by A.L.C. The color red is really on-trend right now. It’s everywhere! While it might be a no-brainer to consider wearing it over the holidays, you can also break up these pieces and wear them all winter. The asymmetrical wrap front jacket can be worn closed or open with a cami or t-shirt underneath. It would look great with black pants or jeans.

The matching ankle-length twill pants have a 26” inseam. They are nearly full-length on Erin and would be cropped on taller ladies. These would be office-appropriate with a white button-down or blouse and blazer. Both pieces are currently on sale so if you have been wanting to add some red to your wardrobe, this would be the time to snag one or both pieces.

Which of these looks is your favorite? Please share your thoughts in the comment section below!

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