Four COMFY Dressy Casual Holiday Outfits🎄

Huge thanks to Nordstrom and ShopStyle for sponsoring this post

The holidays will be unique this year for sure!  While we may not have the usual large family gatherings, in case you have a holiday lunch at work or want to dress up a bit for an intimate celebration with your family, I’m sharing a few COMFY dressy casual holiday outfits in partnership with Nordstrom and ShopStyle.

If you haven’t heard me say this yet, Nordstrom is one of my favorite stores to shop at because they have great items that are COMFY!  And comfy is a MUST, especially around the holidays when lots of food is involved!  (Is anyone else’s family’s love language FOOD? 😜 )  Plus, I love how Nordstrom makes it so convenient to shop with their free shipping and free return shipping on ALL orders, so I can order multiple sizes and try items without a lot of risk.  I also love their curbside pickup option, where you can order online, then drive up to a store a few hours later and get your order delivered to your car.  And, if you sign up for The Nordy Club, you can earn points on all your purchases which turn into credit towards future purchases.  There are a lot of other benefits to joining The Nordy Club, too, like getting credit for getting your clothes altered there.  Check them out HERE!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.


Fall Bootcut Jeans Outfit: red sweater + bootcut jeans + leopard print booties + grey crossbody bag + black statement necklace Fall Bootcut Jeans Outfit: bootcut jeans + red sweater + grey crossbody bag + black statement necklace

1. Nice Sweater + (Stretchy) Bootcut Jeans + Statement Necklace
This outfit is put-together, but super easy!  (That is, if your necklace isn’t broken like mine. Sad day! 😭 I need to bring a jewelry kit along on our photoshoots, haha!) Elevate the look by opting for a sweater with details like embellishments, interesting sleeves, or a faux wrap and belt at the waist instead of a standard pullover.  The sweater I’m wearing above has subtle puffed sleeves, which is enough to do the trick!

This sweater is a medium thickness and has a ribbed texture on the front and back to give it more visual interest.  Also, the cuffs around the wrists are much longer and more dramatic.  If you don’t prefer that, you can do what I did and fold them up a bit to shorten them.  I bet you can’t even tell! 😃 See the original sleeves on the product site HERE.  The one I’m wearing is nearly sold out, but there’s a super similar one HERE, along with several other sweaters in the widget below!  It’d be great for work with black or grey pants, or you can wear it in a dressy casual outfit like I did here with bootcut jeans!

These are the Wit & Wisdom bootcut jeans I’ve told you about for years.  They are VERY STRETCHY and COMFY and have elastic in the waistband for extra comfort!  That elastic in the waistband is crucial during the holidays!  My family celebrates holidays primarily through food, so stretchy waistbands are crucial. 😜 I size up to 8 in the bootcut jeans for a better fit around my fuller thighs.  If you don’t have fuller thighs, other PMTers have said they went with their regular size.  Check them out HERE.

Last, I finished the outfit with leopard print booties.  You could go for solid black ones as well.  When wearing boots with bootcut jeans, I usually prefer ones with an almond toe or pointy toe as opposed to a wider round toe, because they elongate your leg line.  It’s easy for your feet to get cut off in bootcut jeans, so shoe with an extended toe helps keep your leg line longer.

Shop the Outfit:
Sweater: c/o Nordstrom (exact–wearing size S, similar, similar)
Jeans: Nordstrom (exact–wearing size 8, similar)
Shoes: (similar)
Bag: Nordstrom (similar)


Fall Jeans Outfit: red sweater + skinny jeans + taupe suede booties + grey crossbody bag + gold fringe statement necklace + tan leather earrings Fall Jeans Outfit: skinny jeans + red sweater + grey crossbody bag + taupe suede booties + tan leather earrings + gold fringe statement necklace

2. Nice Sweater + Skinny Jeans + Booties
Here’s another look with the same puffed sleeve sweater, this time paired with skinny jeans and booties.

These jeans are my go-to Wit & Wisdom skinny jeans.  They’re super duper stretchy, but they run really large.  Be sure to size down, or you’ll have way too much material everywhere.  They don’t have the elastic strip in the waistband like Wit & Wisdom’s Ab-solution line does, but their waistband still has some stretch and give.  Check them out HERE.

If you’re looking for a pair with elastic in the waistband, my other go-to pair is THESE.  The major difference between them is the length.

Shop the Outfit:
Sweater: c/o Nordstrom (exact–wearing size S, similar, similar)
Jeans: Nordstrom (exact–wearing size 4, similar–I wear size 4)
Shoes: c/o Nordstrom (similar–I wear size 9)
Bag: Nordstrom (similar)
Necklace: Nordstrom (similar)

Fall Leggings Outfit: green v-neck sweater + black leggings + black suede boots + grey tote + gold circle pendant necklace + leopard print leather earrings Fall Leggings Outfit: black leggings + green v-neck sweater + grey tote + black suede boots + leopard print leather earrings + gold circle pendant necklace

3. Leggings + Tunic Sweater + Tall Boots
Here’s an outfit that appears dressy but is super, super comfy with leggings and a loose tunic sweater!

I’m wearing my go-to Zella leggings, which are super thick and not see-through, since they’re activewear leggings.  They work great for dressier casual looks with a loose tunic sweater and tall boots, too!  These are PMT fan favorites, but in case you haven’t tried them yet, in addition to being super thick and not see-through, they have some compression to keep things a little more secure, and have a high, wide waistband to flatten your midsection and help the leggings stay up.  See all the ways I’ve worn them HERE.  These leggings are on the pricier side, but the price is comparable to a good pair of jeans.  And, you can wear them with so many things in so many ways, from activewear to athleisure to dressy casual outfits! Check them out HERE and HERE.

Shop the Outfit:
Sweater: c/o Nordstrom (exact in other colors–wearing size S, similar, similar— crewneck, similar–crewneck, similar–turtleneck)
Leggings: Nordstrom (exact–wearing size M)
Boots: Nordstrom (similar, similar)
Bag: (similar, similar)
Necklace: (similar)


Fall Business Casual Outfit: white tank + taupe suede jacket + skinny jeans + leopard print flats + maroon bag + gold fringe pendant necklace + gold leather earrings Fall Business Casual Outfit: taupe suede jacket + white tank + leopard print flats + skinny jeans + gold leather earrings + maroon bag + gold fringe pendant necklace Fall Business Casual Outfit: white tank + taupe suede jacket + skinny jeans + gold fringe pendant necklace + gold leather earrings + maroon bag

4. Blouse + Moto Jacket + Jeans
If you live in a warmer climate, or if weather allows, this is a fun option!  A moto jacket instantly dresses up outfits, and it’s one of my go-to options for dressy casual looks.  This one is SUPER lightweight, STRETCHY, and SOFT!  It’s so, so, so comfy.  If you like the look of moto jackets but have always been worried they are too stiff, heavy, or uncomfortable, you’ve gotta at least try this one!  (Remember, Nordstrom offers free shipping and free return shipping on all orders, so it’s easy to order things just to try them out!)

I’m wearing size M, but the sleeves are a *tad* wide on me, so I’m waiting for size S to arrive.  It comes in 4 colors HERE.

Shop the Outfit:
Tank: c/o Nordstrom (exact–wearing size M, similar, similar)
Jacket: c/o Nordstrom (exact–wearing size M but want to try S, similar, similar)
Jeans: Nordstrom (exact–wearing size 4, similar–I wear size 4)
Shoes: (similar, similar)
Necklace: Nordstrom (similar)

If your dressy casual options aren’t comfy and you want to step up your game, you DEFINITELY need to check out some of these options!



Hey, hey!  Did you hear?  The Winter Starter Kit Checklist is now available!  If you want a quick list to start a mix and match winter wardrobe, download the free checklist by filling out the form below.  This list easily turns into 14+ outfits!

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