How to Wear Black Pull-On Pants Three Ways for the Holidays

We are officially at the start of Thanksgiving week, that wonderful stretch of days when the kids are finally home, the house feels full again, and your social calendar suddenly kicks into high gear. Between work, family, errands, and everything that piles up this time of year, getting dressed needs to be simple. Having a few easy outfit ideas ready to go makes all the difference.

Today I am taking a simple pair of black pull on pants and showing you how to wear them three ways for the holiday season.

These looks are polished, comfortable, and perfect for the cozy but busy weeks ahead when you need to look chic without putting in much effort.

The pants I am featuring today are The High Hopes from AYR. They are $165 and come in sizes XS through XXL with short, regular, and long inseam options. I took the size Medium in Long.

They are made from a beautiful blend of 58% Pima Cotton, 39% Modal, and 3% Spandex, milled in Peru, and the fabric feels incredible. I received them back in July, but we were on our way to the beach for the rest of the summer and I tucked them on a rack and forgot about them. When I rediscovered them this fall, holy moly. They are fabulous. The fit is smooth and polished, the drape is perfect, and the waistband is comfortable enough for all day wear while still looking pulled together.

If you do not want to spend on the AYR pair, it really comes down to personal preference and budget. A fantastic mid-range option is the Juliet Slim Full Length Ponte Pants from Chico’s. They are usually around $119, but they go on sale often and right now they are about $71. They come in a wide range of sizes with multiple length options, including regular and petite, which makes getting a great fit easier. The ponte fabric is smooth, flattering, and ideal if you want something polished and structured without spending over $150.

If you want something even more affordable, this Amazon pair has been a best seller for us all year. They are under $30, come in several inseams, and offer the same easy pull-on comfort with a wide leg that looks surprisingly elevated for the price.

How to Wear Black Pull-On Pants Three Ways for the Holidays

Travel Day

Maybe you are packing up the car and heading out of town. You want to be comfortable for the drive but still pulled together enough to stop for dinner on the way or walk into a Thanksgiving celebration as you arrive. This look is warm, easy, and quietly chic.

We started with the black pull on pants, then added the Marcie Fair Isle Yoke Knit from Varely. It is a splurge, but it is one of those pieces that earns its keep if you live in a cold climate or spend any time skiing or at the mountains. The texture and weight make it feel special without trying and it’s great if you can’t wear wool.

For shoes, I added the Rothy’s Casual Clogs. I have the braided style and they are fantastic, and this is coming from someone who is not usually a clog person. They are perfect for casual gatherings, especially when you know you will be on your feet most of the night. Rothy’s is also having a great sale so it’s the perfect time to grab something you’re eyeing.

If you are wearing a turtleneck like this, I would pull your hair into a ponytail or loose bun and add a pair of big earrings. This pair from Chicos is oversized and feels a little Tuckernuck inspired but for less.

To finish the look, I added my favorite shade of red for your nails and a large Boat and Tote bag. It is great for corralling all the hosting gifts and the last minute things you toss in as you head out the door.

Set Up Day

This kind of look always makes me think of Chessy in The Parent Trap. She had that effortless, approachable style that felt like a hug and also wildly competent. So whatever day you are doing the bulk of the prep or organizing, you do not have to look like a bridge troll. You can be pulled together without being fussy. I find it makes me feel more energized and helps romanticize the mundane, tedious tasks we all have to do.

For this, I grabbed two J.Crew best sellers: their Vintage Jersey Classic-Fit Crewneck and the Garçon Classic Chambray Shirt. We are just layering them. You can leave the shirt out, fully tuck it, or half-tuck it. Do whatever feels best on your body.

For sneakers, if you already own the black and white Vejas, wear them. If you want something less expensive, the Keds Pursuit Leather Lace Up is on sale for fifty dollars and a great alternative.

Accessories stay simple. Wear your everyday pieces. I added this updated stud from Electric Picks. They are having a fantastic sale right now if you want to try the brand. In case you have to run out for something, grab your crossbody. You already know I love the one from Quince.

Party Day

Our last look could go a million different places, from a bustling restaurant to your friends dining room table. This one is all about feeling elevated while being completely comfortable. We’re keeping our go to pants and adding this very pretty sweater from LOFT. I love the one shoulder bow. It is subtle, and the black and white contrast feels classic and refined.

For shoes, look for something comfortable with a little heel. I’m featuring The Cluny Slingback from Margaux who is having a sitewide sale right now. If you want better quality shoes that are both comfortable and stylish, Margaux is worth checking out. I like that they have a block heel and mix suede with patent leather. When you are wearing a ton of black, that mix adds some much needed dimension.

Then I wanted a pop of color and remembered I just ordered these “emerald” earrings from LOFT on sale for under fifteen dollars. One seasonal color looks so pretty against black, just like the red nail polish in our Travel Day look.

Finally, also from LOFT, I found this satin bag with the bow handle. It ties in perfectly with the shoulder detail on the sweater and gives the whole outfit a festive feel.

It’s as cozy as pajamas, which means you can eat, celebrate, and live your life without ever thinking about unbuttoning your pants.