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5 Casual Holiday Outfits

Casual outfit inspo for the holiday season

No doubt 2020 is the year for casual holiday looks, and I’ve rounded up some of my favorites from my own closets and other blogger friends of mine. Whether you’re celebrating at home or mingling in a small group, I hope these looks give you some ideas of what to wear this holiday season.


Option 1: Wear the Holiday Colors

Whenever any holiday comes around, the easiest way to “match” and look festive is to wear the colors of the season. Christmas? Red and green. Valentine’s Day? Pink and red. 4th of July? Red, white and blue of course!

During the winter holidays, you can instantly look festive with simple pops of green, red, dark blue, silver and gold, either in your outfit choices or your accessories. Some ideas to help you pull this outfit idea together:

    1. Choose A Skirt That Looks Festive

      You can always wear a solid color, but I like to play around with prints,
      whether that be polka dots or plaid, it always makes me feel festive! I’ve
      rounded up some of my favorite midi skirts below!

    2. Wear Your Comfiest Denim Jacket

      You can’t go wrong with a denim jacket, especially if you’re going for a
      casual, everyday look. Denim jackets have always been a closet staple of
      mine during the holidays and, as you can see, it completes any outfit!

    3. Stylish Booties

      You can’t complete your midi skirt look without a cute pair of booties! I
      usually opt for comfort, but it’s easy to find a pair that has it all! I’ve
      rounded up some of my favorites and some that I have my eye on below!


Option 2: Sweater, Jeans and Strappy Heels

Another one of my favorite casual holiday looks is nothing but a cute sweater, some skinny jeans and simple pair of strappy heels. This look will be perfect for every holiday occasion and it’s so easy to recreate. I found an example from Fox and She pictured below. I’ve also compiled a bunch of options you can shop!


Shop This Look

Option 3: Sweater Dress and OTK Boots

Is anything cozier than sweater dress with over the knee boots?! I love how this look can be casual enough to stroll at an outdoor mall or have lunch with a friend — not to mention it’s easy to dress up for the evening.


Shop the Look

Option 4: All Black Look With A Statement Coat or Sweater

It’s pretty much impossible to go wrong with all black any time of the year, but especially in the fall and winter. Add a colored sweater or an oversized jacket with a pop of color, and you’ve got an effortlessly chic look. My favorite Spanx leggings are a wardrobe essential to make this look happen in 2.5 seconds.


Shop the Look

Option 5: Classic, Casual Holiday Plaid

Plaid is synonymous with the holiday season, and there are so many fun ways to integrate it into your wardrobe: coats, skirts, scarves, shoes … the list goes on!


Shop the Look

Casual For The Holidays

No matter how you’re celebrating the holiday season, I hope it’s a bright and happy time for you! If you end up recreating any of these looks, I’d love to see! Tag me on IG {@LifeWithAshleyT}, and let’s connect!!

Ashley T
Ashley T

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