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Three Ways: Comfy Holiday Pants

Nov 17, 2025

We have no Thanksgiving plans. We’re not sure how it happened. But by the time we realized, it was too later to arrange anything but reservations. Living far from family and having jobs that make travel difficult, this was probably inevitable. So my attire for our relaxed dinner out will include my favorite comfortable pants. Here are some ways to style them.

The Pants. These Faherty Stretch Terry Patch Pockets look like denim, but feel like stretchy pants. I have them in olive (gifted) and ivory (purchased). The sizes run 24-33, and run true to the size guide. They also come in ankle length and full length. I own both, and prefer the ankle length for summer, since I can wear the longer length with boots.

Casual. For all three looks, I chose sweaters. It’s an easy combination this time of year. This striped sweater from Pistola is one of my favorites. I bought it on a whim and found myself wearing it almost weekly. Okay, weekly. Why pretend?

I like when the color of your pants coordinates with the color of your shoes. These olive sneakers from New Balance are a chic ‘Mom sneaker.’ If you want a trendier, but more versatile, option, try this dark brown pair from Nike or this Dolce Vita pair.

Accessories start with this chic and simple bag from the Portland Leather Company in a gorgeous plum. I had never heard of Portland Leather Company before, and the bags look like a great option for something cool under-$150. And, of course, I coordinated the color of the bag with the Bobbi Brown Lip Balm. My friend Jayne introduced me to this product, and it’s amazing.

Finish the look with a half-up hairdo, and a cute Quince earring to take advantage. The texture on these hoops just gives them a little something extra.

Relaxed Dressy. What makes one sweater dressier than another? In this case, the relaxed J.Crew turtleneck gives you an elevated sweater look. And then, the styling lifts it the rest of the way. If you want something more fitted, a navy turtleneck is also a great option.

The first elevator in this look is the velvet Mary Jane from Sam Edelman. Velvet just feels just a bit more dressy. The buckles are also a nice detail. For a non Mary Jane, Birdie’s has these satin flats with a crystal bow to lift any outfit this holiday season.

This look has a tote bag because you might need a way to haul wine to a party and leftovers home. This Quince tote is an awesome choice for a second work bag.

To complete the elevation, let’s talk about these earrings. From GLDN, these disc studs with a light blue stone are super chic. I would wear my hair up just to show them off. They come in several metal hues.

As for the makeup, I recently tried this Armani longer liquid shadow. If you want your makeup to last all night, this is the one you need. I like this champagne hue for every day.

Fancy. That may be a relative term, but an off-the-shoulder sweater always feels a bit sultry to me. Or maybe I just saw Flashdance clips too much during my 80s childhood. Regardless, this black sweater from Tuckernuck is a chic option for any holiday party.

Need one for under-$100? Everlane has you covered with this sweater that comes in several colors.

This sweater and an updo look great with any big earring. These Monica Vinader hoops are a more contemporary option. You could also choose these earrings from Sezane that have a more natural look with a swirly resin.

I finished up the look with these black-forward leopard shoes. If you like leopard and wear a lot of black, make sure the print has black hues in it. These Gentle Souls block heels are comfortable and chic for work. Then add this impossibly sophisticated Veronica Beard clutch for that extra something.

And what black sweater and updo look would be complete without red lipstick? This Dior shade looks classic and isn’t too orange. I also love the shiny, glossy effect.

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  1. Ana says:

    Hi, by any chance have you used the Clinique Black Honey Almost Lipstick before? If yes, how does it compare to the Bobbi Brown Lip Balm? Thanks!

    • Belle says:

      I wore black honey for two decades. I would say the formula for the Bobbi Brown is more moisturizing, more of a balm. But the color is very similar, the BB has slightly more berry.

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