Day-to-Night Jeans From Levi’s (Holiday Parties Included)

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This Post is Sponsored By Levi’s.

You can never go wrong with a pair of Levi’s, and that rings especially true for me during the holiday season. When I want a solid, go-to holiday look, I know I can rely on a great pair of jeans to do the heavy lifting for me. We have enough to worry about during this busy time of year without stressing about what we have to wear.

So the no-brainer solution to getting dressed during the holidays? Amazing jeans. The best time to shop is right now where you can get 40% off sitewide at Levi’s for Black Friday!

When you need a look that feels stylish, in that “oh, I just threw this on” kinda way, then you’ve come to the right place! Levi’s has you covered with all things incredibly cute.

Two Levi’s Jean Outfits That Make Holiday Dressing Way Easier

Jacket (S) | Cardigan (S) | Jeans (27)

The Two Pairs of Levi’s I’m Wearing on Repeat This Holiday Season

Enter: the two pairs of Levi’s I’ll be wearing on repeat this holiday season. One, effortless cool and classic (these Wedgies), one polished and trendy (these Baggy Dad Jeans), both up to doing all the holiday styling heavy lifting.

Two pairs of Levi’s, two totally different vibes. And when paired with the coziest red puffer and the softest cardigan ever, you’ve got two solid outfits that will take you from coffee runs to holiday cocktails and back again.

Jacket (S) | Cardigan (S) | Jeans (27)


Outfit 1: Wedgie Straight Ankle + Red-On-Red Layers

Honestly, it’s hard to think of a more classic and timeless pair of jeans than Levi’s Wedgie Straight Ankle jeans. I’ve been wearing Levi’s Wedgie Straight Ankle jeans for literal decades now, and as much as I love the baggy jean trend I have been really itching for a more classic, straight-leg denim vibe and boy, oh, boy did these hit the mark for me this year.

Jacket (S) | Cardigan (S) | Jeans (27)

When I put these jeans on (I’m wearing the Invest Access Medium Wash with the 28″ inseam) I was utterly delighted with how cool and timeless this denim silhouette really is, especially when paired with a chic pair of black pointed-toe mules. Add in Levi’s absolutely fantastic bright and happy Western Bubble Shortie Puffer Jacket and their Supersoft Crewneck Cardigan (it is seriously SO soft) in true red and you have one of my favorite holiday looks to date.

Jacket (S) | Cardigan (S) | Jeans (27)

And honestly, they are just super fun to style. Cuffed, uncuffed, with a slimline sneaker, ballet flats, or a pointed-toe heel, it all works. What I love about these Wedgies is besides being timeless, they ground everything you pair them with. I mean, in any other case, this red-on-red situation might look overwhelming or too holiday “try-hard” but the Wedgies just give this outfit a wearable, relaxed balance.

Jacket (S) | Cardigan (S) | Jeans (27)

FIT NOTES: These jeans are made from 99% cotton and 1% Lycra, so they have that extra little bit of stretch to them that makes them oh-so-easy-to-wear but they still look like the vintage Levi’s styling that I love so much. I found that these actually run true to size for me. They run snug through the hip and thigh, have a high-rise of 10 7/8″, have an inseam of 26″ and a leg opening of 14 1/2.”

Cardigan (S) | Jeans (27)

And finally, what I love about these Wedgies (and pretty much all Levi’s, for that matter) is that they hold their shape and highlight the booty just the right amount, even for someone like me who is seriously lacking in that department. A classic is a classic for a reason.


Outfit 2: Baggy Dad Jeans + Black Puff + Pointed-Toe Flats

These Levi’s Baggy Dad Jeans in Rebel Edge Black are the more updated black denim silhouette that my closet was seriously lacking. They are the cool-girl jeans I am reaching for this year. The washed-black finish gives these jeans a slightly edgy vibe and the drapey leg looks so good with a more dynamic, show-stopping top like when it’s paired with a bright red (and seriously so soft) cardigan and the Western Bubble Shortie Jacket, adds instant drama with not a sequin required.

Jacket (S) | Cardigan (S) | Jeans (27)

These Baggy Dad Jeans are perfectly slouchy in a way that feels “effortlessly intentional” and paired with the same soft red cardigan and cozy Western Bubble Shortie Jacket as worn in the first outfit (holiday dressing efficiency at it’s best, because why change what works so well on top?) the look becomes a laid-back yet totally elevated combo that is cozy enough for daytime, but when paired with a cute pair of pointed-toe bow flats and a beaded evening bag, suddenly we are party-ready.

Cardigan (S) | Jeans (27)

What makes the Baggy Dad Jeans holiday-worthy is how they balance everything else: the extra volume of the legs is cool, the wash is dressy without being fussy, and they offer a denim silhouette that a pair of skinny jeans simply cannot. They give the whole outfit that modern, slightly oversized look that still feels polished, especially with a sweet pair of black flats peaking out from underneath.

Jacket (S) | Cardigan (S) | Jeans (27)

FIT NOTES: Let’s do a quick fit rundown. These jeans fit a little tighter in the waist then I was expecting, I definitely would suggest ordering a size up, especially if you are looking for a more relaxed, baggy fit. I went with my regular 27 here, but would gladly exchange for a 28. These jeans come in different great color options, are loose through the leg and hip, feature a tapered ankle, and a mid-rise (which on me, felt more like a high-rise since my jeans were a tad too small). They are made from 100% cotton, twill, and are non-stretch. They have a zip fly, and 5 pocket styling.

Cardigan (S) | Jeans (27)

I will get a TON of wear out of these jeans this winter, especially during the holiday season. Since they work with anything and everything from sequins, feathers, velvet, even a ridiculously amazing fair-isle sweater! They work also with just about pair of shoes too. There the perfect jeans to wear when you want to look and feel comfortable.


Thank you so much for reading! And thank you to Levi’s for sponsoring this post, I am a lifelong Levi’s fan and it’s truly an honor to get to represent one of my all time favorite and most worn brands. Shop now during Black Friday for 40% off Sitewide! Also, thank you to my talented aunt, Debi D. for the pics. I love the memories we get to make hanging out together. Happy Holidays!

xo, Jess ( My Instagram | More of My Posts )

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