Two Weeks of Everyday Winter Outfits

These first few shots go back to Christmas Eve… which somehow feels like it was forever ago. That morning, Becca and I headed to the mall to knock out a few last-minute gifts, and it was actually really fun. Everyone seemed to be in a good mood, the stores were fully decked out for the holidays, and we managed to cross everything off our lists—including a few requests from other family members.

For my outfit, I kept things simple: a red sweater with darker-wash, relaxed bootcut jeans and black leather Chelsea boots.

Jenni Kayne Flynn in Crimson (S) (similar for less) // MOTHER Bookie Sneak (29) (similar for less) // similar link necklace // similar gold hoops

This Barbour Winter Beadnell Waterproof Jacket has filled a major gap in my winter coat wardrobe. I needed something casual and practical that still feels polished, and this one checks all the boxes. It’s waterproof, has light insulation for extra warmth, and the plaid lining is such a classic finishing touch.

I added simple gold jewelry and a black bag to finish things off. Nothing complicated, but the red sweater felt like a subtle nod to the season, and the relaxed bootcut silhouette keeps the look feeling modern, with the darker wash adding to that updated feel. I could’ve front-tucked the sweater and added a belt, but that felt a little too fussy for a morning of mall errands.

Jenni Kayne Flynn in Crimson (S) (similar for less) // MOTHER The Bookie Sneak (29) (similar for less) // Barbour Winter Beadnell Waterproof Jacket (8) // Quince box bag // similar link necklace // similar gold hoops

I changed for our Christmas Eve service that night because I wanted to be slightly more dressed-up. I swapped the red pullover for a green cardigan, traded the blue jeans for washed-black denim, and changed out my block-heel Chelseas for a suede pair with a low stiletto heel. I added a bold pendant for a little extra pizzazz, and although I don’t have a photo, I finished things off with my heather black Aritzia topcoat.

Aritzia The Only Coat in Heather Black (S) // similar Vince cardigan (similar) // MOTHER Hustler Roller Sneak (39) (similar for less) // Veronica Beard Kelby Bootie (8.5) // Jane Win pendant // similar link necklace // similar gold hoops

Christmas Day was a casual one at home with just the five of us. I was up early prepping our breakfast casserole, stuffing stockings, and doing a bit of last-minute gift wrapping. I threw on my trusty J.Crew cardigan with my SPANX wide-leg pants when I got up and wore that for most of the morning. After breakfast and presents, I switched into black jeans and flats for the rest of the day.

J.Crew Cashmere Patch Pocket Cardigan (S) (similar for less) // MOTHER Dazzler (30) (similar for less) // Margaux Flats (8.5) (similar for less) // similar earrings & necklace

I was up bright and early the day after Christmas to hit the grocery store and stock up on food and drinks for our Shane family Christmas gathering, which was supposed to be the following day. I kept things casual in relaxed jeans, sneakers, and my cozy Frank & Eileen popover henley.

Frank & Eileen Patrick Pullover c/o (S) // MOTHER Lil Kick It (30) (similar for less) // adidas Handball Spezial (8.5) // similar earrings & necklace

That evening, I started coming down with a head cold, and we were also getting a mix of sleet and ice that was expected to impact travel the next day. Half of our family had already canceled earlier in the week due to illness, so we decided to call the whole thing. It was disappointing, but it felt like the right move. I spent most of the next day on the couch—no outfit photos from that day either.

By the time Sunday rolled around, I was feeling a little better. It was still icy and messy outside, so I dressed casually for church in a monochromatic look. These waterproof suede boots are incredibly cozy and have great traction for slippery surfaces.

Barbour Winter Beadnell Waterproof Jacket (8) // Jenni Kayne Flynn in Shadow (S) (similar for less) // MOTHER Dazzler (30) (similar for less)// La Canadienne Kiki (8.5) // similar bag // Oliver Peoples frames

Monday was another lazy day at home with no outfit photos, but Tuesday was the day we headed to Virginia to visit my family, so I did the full hair-and-makeup routine. I also managed to sneak in a few EVEREVE try-ons before getting dressed for the trip, and since this post is a shorter one, I thought I’d include them here.

This green sweater is such a beautiful color, and I love the brushed alpaca-blend knit. It’s incredibly cozy with an easy fit and a flattering V-neck, and I really appreciate the generous sleeve length. It’s slightly short but not cropped, which makes it easy to throw on and go—no tucking required.

Pistola Kit V-Neck Sweater (S) // MOTHER Lil Kick It (30) (similar for less) // adidas Handball Spezial (8.5) // Oliver Peoples frames

This ruby-striped pullover with the collar and three-button placket is a fun one—I love the color combo, and it’s super soft and cozy. The drop shoulder is a deal breaker for me personally, but otherwise it’s really cute.

Roslyn Rugby Stripe Sweater (S) // MOTHER Hustler Roller Sneak (30) // Dolce Vita Faint H20 (8.5)

This striped pullover is 100% cashmere, so it feels like a bit of an upgrade. I love the design and color palette, especially the flattering raglan sleeves. The angled stripes along the upper arm help soften the shoulder line, but it’s a tad small on me—I definitely need the medium.

Ruth Multi Stripe Cashmere Sweater (S) // MOTHER Hustler Roller Sneak (30) // Dolce Vita Faint H20 (8.5)

For our travel day, I went back to the red Jenni Kayne sweater, paired with full-length relaxed straight-leg blue jeans and my favorite adidas sneakers, and I wore the Barbour Beadnell jacket. We didn’t have any plans to go out while we were in Virginia, so I kept things casual and comfortable.

Barbour Winter Beadnell Waterproof Jacket (8) // Jenni Kayne Flynn in Crimson (S) (similar for less) // MOTHER Lil Kick It (30) (similar for less) // adidas Handball Spezial (8.5) // Away The Bigger Carry-on Flex // Oliver Peoples frames

I only packed one change of jeans and two tops for the three-day trip, along with my Birkenstock clogs for hanging out at my parents’ house—and I didn’t take any outfit photos while we were there. It was that kind of trip. We spent our time just hanging out and visiting with my parents and my brother’s family, although I did manage to sneak in coffee with my best friend from high school on our last morning. We talked nonstop for three hours and didn’t even think about taking a picture until I was already on my way home. Next time!

Our first day back was spent mostly at home, putting away the last of the holiday decorations and getting the house back in order. I just threw on my trusty J.Crew cardigan again with comfy old knit pants and slippers.

J.Crew Cashmere Patch Pocket Cardigan (S) // similar Athleta pants // similar UGG slippers // Oliver Peoples frames

The next day was Saturday, and I had Pilates in the morning, a graduation party in the afternoon, and a get-together with friends that night! I went ahead and got myself fully showered and made up before class so I wouldn’t have to deal with it afterward.

These SPANX leggings are amazing, by the way. I can’t remember who originally recommended them to me, but I love how they shape and sculpt without feeling tight or restrictive.

Vuori Halo Performance Hoodie (S) // SPANX Spanxshape Booty Boost Full Legging (M) // Athleta In Motion Seamless Relaxed Tank (M) // On Cloud sneakers (9)

I changed for the graduation party that afternoon. One of my good friends gifted me this LOFT sweater with lace detailing, and it felt like the perfect dressy-casual option for the event. I paired it with my favorite washed-black wide-leg jeans, and I added black leather booties and silver jewelry to finish things off.

LOFT Lace Trim V-Neck Sweater (S) // MOTHER Hustler Roller Sneak (39) (similar for less) // Vince Sutter Bootie (8) // similar hoops // similar necklace

For church on Sunday, I decided to go bold. This cozy coral cardigan with polished silver buttons pairs beautifully with lighter-wash blue jeans. I debated my shoe choice, but I don’t have many options that are high enough for these jeans, so I went with my Sam Edelman Saige booties in black leather. I also have them in brown suede, but I wasn’t sure I’d like brown with this.

EVEREVE Marilyn Cardigan (M) // AGOLDE Harper (29) (similar for less) // Sam Edelman Saige Bootie (8.5) // similar hoops // similar necklace

They’re a little strong against the light denim and bright pink top, but it works because my hair is so dark—it acts as a “bookend” for the outfit. This is a little styling trick I learned many moons ago. If you’re blonde, you can achieve the same effect with taupe or camel footwear.

I also added a black coat and carried a black bag to make the boots feel intentional rather than like a default choice.

Aritzia The Only Coat (S) // EVEREVE Marilyn Cardigan (M) // AGOLDE Harper (29) (similar for less) // Sam Edelman Saige Bootie (8.5) // similar bag

I didn’t document what I wore yesterday, either, so that’s a wrap! I’m off to an early morning Pilates class, and then I have to take my daughter for dental surgery. Fun times!

I hope this post gives you a little bit of mid-winter style inspiration, and if getting dressed has felt a little blah lately to you too, at least you know you’re in good company.