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How to Dress Up Leggings for the Holidays

How to Dress Up Leggings for the Holidays

Today we’re talking about how to dress up leggings for the holidays, so you can maintain your 2020 comfort level while looking festive and chic. Because, if ever there was a year to embrace loungewear as holiday attire, I guess this is it.

First, let’s talk about the kind of legging. Contrary to popular belief, not all leggings are created equal. For these looks, you do not want to wear the leggings you wear to work out.

Just like we keep gym sneakers separate from “dress up” sneakers, leggings follow the same rule. Gym leggings will look out of place.

My hands down, absolute favorite pair of all time are the Zella Live-In leggings. Even though they are sold as work out bottoms, I prefer to use these as my “better” pair. 

These higher-waisted leggings are thick, and pull you in and lift you up while still being comfortable. I have had several pairs for years and I am always amazed at how well the wash. They don’t fade or stretch out over time. 

Zella Live-In Leggings

Zella Live in Leggings


Leggings, $58  

Style note: If you’re not totally comfortable wearing traditional leggings, swap these out for your Spanx Perfect Pants, you’ll feel more finished in them. Want to make these looks extra special? Wear the Spanx Faux Leather Leggings OR their new  Velvet Leggings

For the outfits below I worked with a combination of items I know you have and added in some new affordable pieces to help build out your options. 

How to Dress Up Leggings for the Holidays

How to wear leggings for the holidays

Cozy Glam 


How to wear leggings for the holidays


Sweater, $40  |Loafers, $95 | Hair Bow, $10 Studs, $40  

This first look is simple yet chic. I like leggings because they allow you to wear a big oversized sweater, and this one from Express is fab. It’s on sale for $40 and comes in four colors up to an XL. Above, I’m using the grey because I love the neutral combination. There is also a seasonal red that would look lovely.

Then, I used the Birdie loafers we are all loving, in black velvet. For accessories, a fun pair of CZ studs and a simple velvet bow hair tie I found on Etsy.


Chic by The Fire 

How to wear leggings for the holidays


Sweater, $52 | Thermal Tee, $12 | Booties, $125 Beanie, $19 

Many people are getting creative this year, hosting smaller get-togethers outside. Whether you’re sitting by a fire or snuggled up under a heat lamp, this look would be adorable. I created a simple column of color by adding the popular Old Navy long sleeve tee (another reader fave) as a base. Then, I found (and ordered for myself) this Fair Isle wrap cardigan

When I first saw it, I swore it was expensive, but much to my delight, it’s another Old Navy find for under $50 available in regular, petite, and tall sizes. 

Then I used these Sam Edelman tan booties. In our INSIDER group, we talked about when you can wear tan shoes with black bottoms and when to keep it to all black. My best tip is to add the tan to a look when it is casual because it will elevate it and add interest. If the outfit is more formal, keep it to black. 

Finally,  a hat is a fun accessory. You’ll stay warm and bonus points since you won’t have to do your hair.

Classic Combo 


How to wear leggings for the holidays


Tunic, $25 | Earrings, $12 | Mules, $88 | Lipstick, $28 

This last look is as easy as it gets. Add a long white tunic, like this one from J.Crew in all sizes up to 3X for $25. You want this to feel and look oversized. 

I love the look of an over-the-top earring with a collared shirt. It feels dramatic and perfect for the holidays. Here I used this $12 pair, also by J.Crew. These are big and will add some movement and glamour. 

Speaking of glamour, holidays at home should be a little extra, so I went with these gold fur-lined slipper/loafers and, for an added touch of flair, a bold red lip with my go-to brand Kosas. 

Tell us below, what are you planning on wearing at home this holiday?

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Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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How to Dress Up Leggings for the Holidays

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Monday 7th of December 2020

Love this post Megan! Immediately went to order the Old Navy Fair Isle cardigan but darn it's not available in Canada. If I find something similar I'll post on the FB group.

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