Two Weeks of Everyday Winter Outfits

SIZING NOTES: I’m 5’5″ and typically wear a small or medium in tops and dresses, a 29–30 in jeans and pants, and a size 8.5 shoe. I often fall between sizes, so fit notes matter. Gifted items are marked c/o; everything else was purchased by me.

Two weeks ago, I wore this vintage-inspired grey marl raglan sweatshirt with barrel jeans and Birkenstock clogs for a casual work-from-home day. The sweatshirt is so cozy, and the jeans are surprisingly comfortable, especially considering they’re a more rigid denim. I really like the barrel shape, too.

EVEREVE Heritage Sweatshirt (S) // Citizens Miro (29) (budget option) // Birkenstock Boston Rivets (39) // Tom Ford frames

The next day, I had a nail appointment followed by a lunch date. I went with a simple black sweater and jeans and added black boots to bookend the look. Then I layered on a few accessories for interest, and topped it off with a camel coat for a warm contrast. It’s a super simple outfit, but I really love the color combination and proportions.

J.Crew Chiara Topcoat (6) // Jenni Kayne Flynn in Black (S) // MOTHER Lil Kick It (30P) (similar for less) // Madewell belt (M) // similar rag & bone boots // Yurman hoops (similar for less) // similar necklace // similar pendant // Yurman bracelet // Quince box bag

I wore this casual look to travel to Tampa last week, tagging along on Paul’s work trip. It was freezing here in Philly when we left, but it was going to be in the 80s when we arrived, so I layered a white tee under the sweater so I could take it off once we landed. I also chose pieces I knew I could mix, match, and rewear throughout the trip to keep everything to a carry-on.

J.Crew Chiara Topcoat in Camel (6) // Quince crewneck in Charcoal c/o (S) // AllSaints Anna (M) // Citizens Miro (29) (budget option) // rag & bone belt (M) (budget option) // adidas Spezial (8) // Yurman hoops (similar for less) // similar necklace // similar pendant // AWAY Bigger Carry-On & Featherlight Backpack

That night, we met a couple of Paul’s work colleagues for drinks and a casual dinner in the hotel bar. I just wore the t-shirt, jeans, and sneakers.

AllSaints Anna V-Neck (M) // Citizens Miro (29) (budget option) // adidas Spezial (8) // rag & bone belt (M) (budget option) // YSL Niki Baby (similar for less) // Yurman hoops (similar for less) // similar necklace // similar pendant // Yurman toggle bracelet

Sunday was pretty open since Paul’s meetings didn’t start until Monday. (We flew in a day early to get ahead of the snowstorm.) We started the day with a leisurely walk along Tampa Bay, and I wore a Vuori tank and pants. I wasn’t sure how cool it would be by the water, so I threw a sweatshirt over my shoulders.

Vuori Energy Top Long (M) // Vuori Halo Modern Straight Leg Pant (M) // Xero HFS II (8.5) // Heritage Sweatshirt (S) // Celine sunnies

We changed once we got back to the hotel and went out for brunch. Since it was another warm day, I used the opportunity to break out my new green cable sweater tee and paired it with wide-leg jeans. I finished the look with suede pointy-toe flats and a coordinating belt.

I was actually a bit too warm in this, as it turned out (we had to walk outside for a bit) but I was glad I got a chance to wear the green sweater. Who knows how long it will be till I’m wearing short sleeves in Philly.

Vince Cable Short Sleeve Sweater (M) (similar for less) // PAIGE Anessa (29) // Vince Bancroft Flats (8.5) // similar belt // Yurman mixed metal hoops (similar for less) // similar necklace // similar pendant

Later on, we took an Uber into downtown Tampa for drinks and dinner. It was still warm out, so I switched back into the white tee from the night before. I knew we’d be doing some walking, so I wanted to wear the sneakers for comfort. I guess it looked okay. Everyone was pretty casual.

I tied the grey sweatshirt around my shoulders just in case it cooled off, which actually worked out really well—it added just enough warmth without needing to put it on, and I could easily slide one arm out of the knot at the restaurant, then slip it back on when it was time to leave.

AllSaints Anna V-Neck (M) // Heritage Sweatshirt (S) // PAIGE Anessa (29) // rag & bone belt (M) (budget option) // adidas Spezial (8) // Lili Claspe earrings // similar necklace // similar pendant // Yurman bracelet // similar bag

I had the next day all to myself, and since it was a bit chilly, I wore this ribbed tee with jeans and sneakers while I worked from the hotel most of the day.

bobi ribbed button-up top (M) // Citizens Miro (29) // adidas Spezial (8) // Oliver Peoples frames

That night, we headed over to the mall to walk around and grab dinner. It had turned quite cold, so I switched back into my travel outfit with the cashmere sweater and camel topcoat, and I was very glad I did. Who knew Florida could be so cold?

J.Crew Chiara Topcoat (6) // Quince cashmere crewneck (S) // AllSaints Anna (M) // Citizens Miro (29) // rag & bone belt (M) (budget option) // adidas Spezial (8) // similar bag // Oliver Peoples frames // similar necklace // similar pendant

I threw on the same sweater and tee with my Vuori straight-leg pants to work in the hotel lobby for the better part of the next day.

Quince Oversized Cashmere Crewneck (S) // AllSaints Anna (M) // Vuori Halo Modern Straight Leg Pant (M) // adidas Spezial (8) // similar hoops // Oliver Peoples frames

Then I changed to meet Paul and a few of his colleagues for drinks in the hotel bar that evening before they headed out to a work dinner. I finally got a chance to pull out the oatmeal v-neck sweater I brought and wore the suede flats again. I was happy to make use of everything I packed at least once or twice—that’s always my goal. I hate packing things that don’t get worn.

Jenni Kayne Flynn in Oatmeal (S) (similar for less) // MOTHER Lil Kick It (30P) (similar for less) // Vince Bancroft Flats (8.5) // similar hoops // Oliver Peoples frames // similar necklace // similar pendant // similar earrings

I started our last full day in Tampa with a gym workout. I have a rule that if I pack workout clothes, I have to use them at least once. I waited until the last day this time, but it still counts… right?

Vuori Energy Top Long (M) // Vuori Clean Elevation Leggings (M) // Xero HFS II (8.5)

After that, I showered and changed into my black ribbed top and MOTHER Lil Kick It jeans to meet a friend who lives in the area for shopping and dinner.

bobi ribbed button up top (M) // MOTHER Lil Kick It (30P) (similar for less) // adidas Spezial (8) // Yurman hoops (similar for less) // similar necklace // similar pendant

I added the camel coat since it was still chilly out.

J.Crew Chiara Topcoat (6) // bobi ribbed top (M) // MOTHER Lil Kick It (30P) // adidas Spezial (8) // Yurman hoops (similar for less) // similar necklace // similar pendant // similar bag

The next day, I wore the Quince cashmere sweater again for the trip home, this time with my MOTHER jeans instead of the barrel jeans.

J.Crew Chiara Topcoat (6) // Quince Oversized Cashmere Crewneck (S) // MOTHER Lil Kick It (30P) (similar for less) // rag & bone belt (M) (budget option) // adidas Spezial (8) // Yurman mixed metal hoops (similar for less) // similar necklace // similar pendant // Oliver Peoples frames

Back at home, I met a friend at the mall last Friday. You’d think I’d be sick and tired of the MOTHER Kick It jeans by now, but nope. I wore them again with this cozy striped cashmere sweater and my Aquatalia waterproof boots. The boots are currently 60% off, but sizes are pretty picked over.

I tried the outfit both with and without a belt, and while I like the focal point a belt adds, the look felt more natural and streamlined without it. The sweater is the perfect length and shape to leave untucked, and I felt like my proportions didn’t need the added tuck to make it work, so I left it out.

White & Warren sweater (M) (similar) // MOTHER Lil Kick It (30P) (similar for less) // Aquatalia boots (9) // similar belt // LAGOS hoops // Anna Beck pendant

And once again, I finished the look with the camel coat.

J.Crew Chiara Topcoat (6) // White & Warren sweater (M) (similar) // MOTHER Lil Kick It (30P) (similar for less) // Aquatalia boots (9) // similar belt // LAGOS hoops // Anna Beck pendant // Mulberry Amberley (similar for less)

I spent Saturday at home, so I pulled on the grey sweatshirt with my Vuori straight-leg pants and Dolce Vita fleece-lined sneakers. They’re so comfortable; they pretty much feel like slippers.

EVEREVE Heritage Sweatshirt (S) // Vuori Halo Modern Straight Leg Pant (M) // Dolce Vita Notice sneakers (8.5) // Jenny Bird Tome Hoops // Oliver Peoples frames

For church on Sunday, I wore this red turtleneck with washed black jeans. It was still cold and snowy, and the red felt like a small nod to the fact that we’d finally made it to February. ❤️

I’m usually not a big fan of red tops with black pants. It can feel a little too predictable and “safe,” like the default office holiday party outfit. But I didn’t feel like wearing blue jeans again, and since these are a washed black denim, the combination feels a little more modern.

Naadam Boxy Turtleneck Sweater c/o (M) // MOTHER Roller (30) // similar boots // similar John Hardy hoops // Yurman bracelet

I topped it off with my Aritzia topcoat in Heather Black and added a black bag. I kept my jewelry minimal, with large hoop earrings, but the outfit could use a pendant of some sort. I was wishing I’d grabbed my Heart On A String necklace.

Aritzia The Only Coat (6) // Naadam Boxy Turtleneck Sweater (M) // MOTHER Roller Hustler Sneak (30) // Vince Sutter (8.5) similar // John Hardy Hoops // similar bag

On Monday, I pulled on the same jeans again and paired them with sneakers. I realized I can actually wear them with flats! This chunky cashmere turtleneck is super cozy and warm, but it sold out, so I linked something similar below.

similar turtleneck // MOTHER Roller Hustler Sneak (30) // Dolce Vita Notice (8.5) // similar hoops

And yesterday, I met a friend for brunch. I wanted to wear this bright blue stripe sweater, so I paired it with high waist jeans and brown sneakers, and topped it off with the brown jacket.

I was toying with my brown scarf coat and even recorded a reel using that one, but I ended up wearing my longer one since it was so cold out. (Pardon my mess of a desk! I just wanted to snap something real quick as I headed out the door… running late, as usual!)

Jessie Cardigan (M) // FRAME Pixie Arrow (30) // adidas Spezial (8) // Madewell Alonzo (S)

And that’s a wrap! There are a lot of repeat pieces here, but I think it’s a good reminder of how far great basics and smart layering can take you—especially when traveling. As always, feel free to reach out if you have questions about fit, sizing, or how I styled anything.