15 Stylish Holiday Pant Outfit Ideas

Stumped on what to wear for the holidays? I’ve got you covered with multiple options including many pant options so you can optimize comfort and still look stylish!

As a personal stylist and Chicago personal shopper, I focus on versatility (most of these pieces you can wear throughout the year, not just holiday time) which is important because you know I do not want you to purchase a “one-and-done” piece, which is what I help clients with during personal shopping and Stylist in Your Back Pocket. 

98% of these outfits are secondhand purchases.  (Places like thredup.com, local resale stores, Poshmark and my super stylish Grandma Jean, to name a few).  

I share this because I feel so strongly about sustainable fashion and secondhand clothing. 

Not only are the pieces so much more unique and affordable but they help our planet.  There are SO many secondhand clothing options available.  I truly believe *small* actions make a big difference when it comes to purchasing secondhand when we’re able. 

Albeit, it still has a ways to go to be more inclusive.  (Secondhand wardrobe is more challenging for plus size fashion. Which I hate but it’s currently what’s so.) 

If you prefer a quick video (under 1 minute), click here to watch the video. 

Using colors uniquely is a fun way to create your stylish holiday outfit.  Plaids, silks and velvets are always in style as well for holiday outfit ideas. 

If it’s wildly snowing or super wet weather during the holidays, you can always and easily pop on a winter boot.  If you haven’t read the blog about my favorite of all-time, tried-and-true winter boot, check out this blog here. 

These are well worth the investment.  I can walk for miles in these professional winter boots and still feel stylish! (And comfortable). 

p.s- you could easily add a skirt if you prefer skirts over pants. 

Notice how often I am repeating this faux leather jacket? That’s what I want for you as well- versatility is key when it comes to getting dressed easily!  I focus on this throughout Stylist in Your Back Pocket and mystery boxes that are sent to your home. 

Remember, stylish holiday outfits can be easily made using the wardrobe you already own with pops of metallic or plaids.

Every piece in the above outfits are preloved and secondhand pieces! (Jewelry and shoes too). 

The sequin bustier is from my grandma and I consider it a holiday staple! 

Notice the difference in the right outfits? Almost identical but with the swap of a pant, they look completely different. 

ps- I flipped this sweater backwards for this look. So the back is a buttoned cardigan! 
This is one of many things you can learn how to do.

How to make your old clothing new again is one of my favorite modules inside of SIYBP! 

I hope you’re able to use these outfits as holiday outfit inspiration to make your getting dressed a bit easier during a stressful season. 

If you want help creating a beautiful collection of mix-and-match outfits, schedule a free consult call here. 


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