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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

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.

The Leggings

Stretch Ankle Leggings EILEEN FISHER

Leggings, $98 


The good news is that there are so many options available, and I know you have at least one of them. For today’s looks I’m using a pair from Eileen Fisher

Expensive? Yes. But they wash like a dream and from my experience Eileen Fisher’s basics wear like iron. 

If you have a pair of the Zella leggings or a Ponte knit from Old Navy, wear them. 

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 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 black leggings for the holidays


I realize there is a lot of black in these outfits. Remember, these looks are meant to be both inspirational and instructional since most of these pieces are also best sellers. 

Cozy Glam 

Black leggings, with ivory turtleneck sweatshirt, black velvet loafers, black hair bow, and pearl earrings

Mockneck Sweatshirt, $22.50 | The Starling Loafers, $98 | Bow Hair Clip, $13 |Pearl Earring, $35 

This first look is simple and chic. I found this fleece turtleneck at J.Crew Factory for $22 and scooped it up. I’m using the Ivory because it looks the most sophisticated.

Then, I used the Birdie loafers we pretty much all own at this point in black velvet and a simple velvet bow hair we featured a few weeks ago from H&M.

Finally, I JUST received these pearl earrings from Julie Vos on sale for $95 and they are gorgeous in person

All Wrapped Up

Black leggings, black turtleneck sweater, gray wool poncho, silver hoops earings, and black over the knee boots.

Turtleneck Wool Sweater, $40 | Striped Poncho, $85 | Hoop Earrings, $115 |Over-the-knee boots, $750 

I wanted to use this poncho from the Banana Republic because I know a few of you have it. I love it thrown over an all-black column. Here I’m using the seamless wool turtleneck, also from BR

If you’re doing a legging with a poncho or cape, you need a shoe that will balance the weight and volume of the top. These Stuart Weitzman over-the-knee boots are an outrageous splurge, but something to consider if you have the budget. 

For something much less expensive, these Vince Camuto’s are nice dupes.

And a pair of modern silver hoops is all you need to tie the outfit together.

Better than Pajamas 

gray animal print tunic, black leggings, and black mules

Tunic, $54 | Mules, $120 |Hoops, $90 

This last look is as easy as it gets. I took the idea of loungewear and polished it just a touch.

Start with a tunic, like this high/low option from Nordstrom is under $60 and still has a size range in stock.

Then I found these beautiful hoops, currently 25% off with the Friends and Family discount at Bloomingdales. I love the shape and how they sit on the ear. 

Lastly, I used a simple pair of black mules or wear your Birdies.


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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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Tuesday 28th of December 2021

What’s your opinion on patterned leggings worn with a longer tunic-type top? Out of style?

Megan Kristel

Tuesday 28th of December 2021

Yes, if your intention is to create a classic, timeless, and stylish look.


Wednesday 8th of December 2021

Ooh, I'm going to try that middle outfit with the BR poncho :) I just ordered a pair of OTK boots from Torrid - haven't received them yet, but when I get it all put together, I'll post a pic in the FB group!

Megan Kristel

Wednesday 8th of December 2021

I was thinking of you when I put it in. :)

Julie Berry

Wednesday 8th of December 2021

That first top looks a bit short. Isn’t it best to have a top that covers your “assets” when wearing leggings. (Unless of course you are a 16 yr old fashion model)

Megan Kristel

Wednesday 8th of December 2021

If you look at the top on the model, it's not too short, especially if you're wearing it with something like the Spanx Perfect Pants.


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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