Skip to content

Warm + Cozy Holiday Outfits (and Jess, Kelly and Krista’s Day Out!)

Warm + Cozy Holiday Outfits

On Me: Dudley Stephens Cobble Hill turtleneck (c/o), Commando leather leggings, J.Crew booties, J.Crew scarf
On Krista: Dudley Stephens Cobble Hill turtleneck, J.Crew tartan shoes, J.Crew tartan pants
On Kelly:  Dudley Stephens Cobble Hill turtleneck, J.Crew tartan pants, J.Crew pumps (old)

WOOOO Happy Monday guys!

Today is my first of many holiday outfit posts! Hooray! (Featuring some special guests ??)

Last week, our friend Krista (do you follow her yet? You should!) was in town from NYC. This was pretty exciting because we’ve been “Instagram” friends since the early years, but we’ve never actually met in person. Krista is actually the entire reason that Kelly and I met–so we are both forever indebted to her, obviously. ?

We decided to plan a little festive day, going to lunch at RL (Ralph Lauren’s restaurant–probably my favorite cozy lunch spot of all time) followed by a fun shoot together! If you follow Kelly, you know around the holidays she does something called #60DaysofPlaid where she posts 60 different plaid inspired looks. (Preppy people LOVE plaid, allegedly?)

Krista and I decided we needed to join in on the #60DaysofPlaid fun and thus we all three decided to each wear J.Crew tartan AND because it was sub-zero in Chicago, we decided that Dudley Stephens fleeces were also in order. ? (Side note: They have been a sponsor of mine but they did not sponsor this post! You can read my full review of BOTH fleece turtlenecks we’re wearing here in this post! I am OBSESSED with these fleeces and the brand! They’re women-owned, made in the USA and sustainable, too!) 

Here I’ll give you all the details on my look and then you can scroll down for the behind the scenes photos from our day!

Warm + Cozy Holiday Outfits

J.Crew Cocoon Coat: 

The coat I never stop raving about–I think it’s the warmest non-puffer you can find! Sizing: It runs big, I’m wearing size 0! Comes in lots of colors but I’m partial to the light camel color! See my full review of it here!

Dudley Stephens Cobble Hill Turtleneck

I literally have not shut up about these fleeces since they first arrived. I am not exaggerating when I say I have worn them multiple times per week ever since. Actually, I wore this burgundy one three days in a row one week! It’s become a problem. The one I’m wearing is the Cobble Hill, which is longer in length (which I was really surprised that I liked, honestly, you know my love of the front tuck) but it is SO WARM and the most perfect thing to wear with leggings!

Kelly and Krista are both wearing the Park Slope, which is a regular length version I love equally as much. I think the Park Slope is more versatile because you can wear it with more things due to the length, but I reach for the Cobble Hill when I feel like wearing leggings! I love both equally!


The Cobble Hill (what I’m wearing) runs tight in the arms–I’m a small, but in the Park Slope (what Kelly/Krista are wearing) I have an XS and that fits great!

Note on price:

I know these definitely qualify as more of an investment piece (which seems odd for a fleece, I know) but a couple things. First, it’s less expensive than a Patagonia fleece, and is a hell of a lot cuter, more versatile, and warmer. Second, DS is a very small, women-owned brand, made in Brooklyn, from yarn made of recycled plastic bottles! When you break it down to cost per wear AND consider that your money goes toward a company doing a lot of good, it’s a no-brainer! ALSO–they will not be running a discounted Black Friday sale, so don’t wait to buy! If you see the color you want, snap it up, because they do limited runs of each and they go out of stock frequently!

Commando faux leather leggings: 

I love both the Spanx and Commando pairs of faux leather leggings! Both for different reasons. The Commandos are more “leather” looking, whereas the Spanx are shiny, but they don’t *feel* leathery, if that makes sense? The Commandos are thicker and warmer (due to the leathery quality that blocks the wind better), but the Spanx are more breathable and more comfortable. I wear both a ton! Sizing note: These run SO SMALL. I wear a medium, and I’m a small in Spanx, so go up a whole size!

J.Crew leopard booties: 

I just got these booties recently at J.Crew and I have worn them almost every day since I purchased them last week. I’m so glad I finally took the plunge and purchased them! I love the pointed toe and low heel. You can see four more ways I styled them in this post! Sizing: Run TTS

J.Crew Tartan Scarf: 

I love this scarf and have had it for a few years now! I think it’s the prettiest tartan pattern and I love the coloring especially–I feel like it’s more unique than other plaid colorways and it goes with everything! It’s the perfect way to add some holiday festivity to an outfit without being overpowering!

Pearl Headband:

Statement headbands are my *THING* this year. They make any outfit so much more interesting, not to mention, they are amazing for extending your hair even further between washes. They’re lifesavers all around! This one is from Lost Girls boutique (highly recommend visiting if you live in Chicago!) but I also found super similar ones on Amazon–you can buy individually right here or get a 6 pack of different colors for so $15!! (Great stocking stuffers for your girlfriends, too!)


Warm + Cozy Holiday Outfits


Warm + Cozy Holiday Outfits

[/one-half] Warm + Cozy Holiday Outfits

ankle boots

Warm + Cozy Holiday OutfitsWarm + Cozy Holiday Outfits pearl headband

Cuff c/o Sezane

Funny outtakes–more from our day!

Lunch at Ralph Lauren: 

Lunch at Ralph Lauren Lunch at Ralph Lauren

We asked our server Jeff to snap a photo for us, but he had some interesting takes on camera angles. ?The best part is that my friend Megan texted me and said, “I went with my mom and sister and had Jeff as our server and HE TOOK THE EXACT SAME HORRIBLE SERIES OF PHOTOS WITH US!!!” ?Apparently, this is Jeff’s schtick and we’re here for it. WE LOVE YOU JEFF!

Shooting with Mitch

Warm + Cozy Holiday Outfits

Then Krista and I invited ourselves back to Kelly’s house so we Krista could get a tour of her new place and also so we could hang out with the girls and ALSO so Mitch could take these photos. (You are the best Mitch!) This is us posing for “test shots” ?while Kelly was testing the lighting. (Light testing photos are always the funniest outtakes ?)

More light testing weirdness…

Warm + Cozy Holiday Outfits plaid outfits

We call these next frames: “Winter fashion blogging, a series.” 

Krista hates Chicago weather and curses every time she’s forced to go outside. ?She was NOT HAPPY about shooting photos in this weather. (Also the best part about shooting with other bloggers is that they know all the things to look for–I.E. “KRISTA your hair is messed up–JESS fix her hair!!”)

mirror selfie

Ended with an obligatory Kelly mirror selfie in her room. AKA the preppiest room I’ve ever seen. (Fun fact: Kelly and Krista are my two preppiest friends, in case you couldn’t tell.) Fact: Noodle is a sneaky devil and has to be held at all times upstairs or she pees. ?

Thanks for tuning into the Kelly, Krista, and Jess show, feat #60DaysofPlaid. Anddddd we’re out! ?