
What I Wore Lately: Two Weeks of Everyday Winter Outfits
Hi, friends! It’s time for another edition of What I Wore Lately! This is a peek into my everyday style—what I wore, where I wore it, and how each outfit came together. Whether you’re looking for styling ideas or just love a little outfit inspiration, I hope this gives you some fresh ways to mix and match pieces in your own wardrobe.
But first, the usual disclaimer: These are my real-life outfits, so you might see some repeats, and a few of the pieces are older and no longer available. I also know that when you add everything up, some of these outfits can get pricey. Over the years, I’ve invested in quality pieces that I truly love, and of course, I try to wear them as much as possible to maximize cost per wear. That said, I’ll link in-stock options and similar-for-less finds where I can!
Real Outfits, Real Life: What I Actually Wore
SIZING NOTES: I’m 5’5″ and I usually wear a small or medium in tops and dresses, a 29 or 30 in jeans and pants, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.
This first look is from two weeks ago, and I wanted to take my new PAIGE Leenah Ankle jeans for a test drive to run some errands. I love how they pair with my adidas Spezials and the ivory sweater, but with the sweater untucked, the outfit felt a little shapeless.
When I got downstairs, I tried a casual off-center front tuck, and I feel like this looks much better. It adds just enough definition at the waist and makes the look feel more intentional.
Side note: I skipped a belt since I don’t have one I love for this outfit, and I feel like the relaxed vibe works without it.
JK Cashmere Fisherman (budget option) // PAIGE Leenah Ankle (29) // adidas Handball Spezial (8) // Clare V. Midi Sac (left) // LV Neverfull MM (right) // similar gold hoops
Since it was a chilly day, I threw on my new Aritzia The Super Puff₂o™ Mid in Modern Taupe. The color works perfectly with these neutrals, and the sporty feel matches the casual vibe. I had a couple of appointments with some downtime in between, so I swapped my crossbody for a tote that could hold my book and a few extras.
Fun fact: This Louis Vuitton tote was my first luxury designer bag. I’ve had it for years, and I pulled it out of the back of my closet because the shades of brown work so well with this outfit.
Aritzia The Super Puff₂o™ Mid in Modern Taupe (S) // JK Cashmere Fisherman (option) // PAIGE Leenah Ankle (29) // adidas Handball Spezial (8) // LV Neverfull MM // similar hoops
The next day, I kept things casual again and wore this athleisure look to run some errands after a photo shoot. (And yes, my ankles were cold—I should have worn my duck boots.)
Zella long puffer vest (S) // Zella Studio Luxe Performance Jacket (M) // Zella leggings (M) // On Cloud 5 running shoes (9)
I changed for the afternoon when I got home, and I just pulled on this comfy sweater, jeans, and sneaker combo… I tried it first with the darker wash jeans, but for some reason, this color combination looks frumpy to me. (And yes, that is the correct link to the exact MOTHER Hustler Flood Fray jeans that I’m wearing on the left; they are darker than they appear on the website.)
After a few hours, I went back upstairs to see how I felt about the same sweater and sneakers with my lighter wash jeans—a look I’ve worn many times already. Sure enough, I like this so much better! Why is that, I wonder???
Jenni Kayne Flynn in Shadow (S) // MOTHER Hustler Flood Fray in What’s Your Sign – left (29) // MOTHER Dazzler in Riding The Cliffside – right (29) // adidas Handball Spezial (8)
Okay, moving on… this was a casual Saturday spent mostly at home. As I recall, Paul was sick and relegated to the guest room upstairs, and David had plans with friends, so I didn’t even bother to put on makeup. We were expecting a big snowstorm the next day, and it was already quite cold and damp outside, so I pulled on duck boots and a coat to run to the grocery store with the rest of humanity. I wanted to make sure we had some good game day snacks in case we got snowed in.
Aritzia The Super Puff₂o™ Mid in Modern Taupe (S) // Evereve Zoey Rib Inset Hoodie (M) // MOTHER Dazzler (29) // Sorel Out-N-About IV Chillz (8.5) // Jenny Bird earrings
By the next day, I was so ready to get dressed and made-up and go somewhere!!! Of course, we still had a lot of snow on the ground, and it was freeeezing, but happily, the roads were clear and my weekly women’s Bible Study did not get canceled.
I decided it was too cold for jeans, so I wore my Athleta Altitude fleece lined pants (excluded from the 30% off promo, sadly) with a cozy sweater, sherpa-lined duck boots, and my warmest turtleneck sweater. I love the vest with this look, but I assumed it would be too bulky to wear under a coat, so I took it off when I left the house and wore this long sherpa coat instead.
Evereve Cooper Quilted Vest – left (S) // old Vince sherpa coat – left // similar sweater // Athleta Altitude Fleece Lined High Rise Pant (M) // SOREL Out-N-About IV Chillz (8.5) // similar bag // Jenny Bird earrings
I had a nail appointment the next day, and I wore the same pants, but this time with a wool/cashmere sweater hoodie and my quilted vest. (I was holding my “pedicure flip-flops“—which I eventually put in my tote bag.)
Side note: This time, I did try to put a long quilted parka on top of the vest, and turns out, the vest is thin enough to fit comfortably under a coat.
I had a photo shoot here at home the next day, and then I ran out to get my annual mammogram. Fun times! This was the last outfit we photographed, so I just kept it on and threw a coat on top when it was time to leave for the appointment.
Aritzia The Super Puff₂o™ Mid in Modern Taupe (S) // Jojo Seamed Sweatshirt (M) // Paige Leenah Ankle (29) // Gola Torpedo (8.5) // similar bag // similar earrings
When I got home, I changed into a warmer outfit—a cozy turtleneck, stretchy jeans, and UGG slippers. This turtleneck sweater is at least five years old—a Vince find from a major end-of-season sale at Saks OFF 5TH or Nordstrom Rack.
I remember it well because my usual size small was sold out, but the deal was too good to pass up, so I grabbed the medium instead. That worked out in my favor, since it still fits! (I often need the medium in Vince sweaters these days.) I love the details—the ribbing at the neck, cuffs, and hem adds a little extra interest. Plus, it has that ideal relaxed-but-not-oversized fit, and it’s so warm.
old Vince sweater (option) // MOTHER Weekender (29) (budget option) // UGG Dakota (8) // similar earrings
I wasn’t really planning to go anywhere that night, but when Paul got home, he suggested we go out and grab a bite to eat, so I swapped my slippers for boots and threw on my taupe puffer coat. My black one would work too, of course, but I think the taupe with black trim makes a pleasing contrast against the black sweater.
old Vince sweater (option) // MOTHER Weekender (29) (budget option) // Franco Sarto Vianca (8) (option) // similar earrings
The next day, I ran to the mall to make a few returns, and I wore this light neutral look. This sweater is another oldie-but-goodie—this time from Naadam. I scored it during one of their Black Friday sales a few years ago, and it has made the cut year after year because it’s such a timeless classic. It’s also a very thick, dense cashmere knit, which is getting harder to find these days.
Aritzia The Super Puff₂o™ Mid in Modern Taupe (S) // similar sweater // MOTHER Dazzler (29) // adidas Handball Spezial (8) // similar hoops
One of my returns was an Aritzia puffer I ordered before I found the one I really wanted—The Super Puff₂o™ Mid in Modern Taupe. It was exchange-only, not refundable, and I also had an Aritzia gift card, so… I ended up coming home with The Super Puff Long.
I’ve been considering a longer, warmer puffer for the coldest days—especially for outdoor walks. I love the oversized, sporty vibe that’s everywhere right now, and this one is exactly what I had in mind. The channel quilting, relaxed fit, and side vents give it that effortless, modern feel. Plus, I love the Aritzia StormSoft Cuffs with thumbholes—they really do help keep the warmth in and the cold out. As soon as I got home, I threw it on to walk the dog, and it totally delivered. I may not wear it a ton, but I know I’ll have it for many years.
I also tried the The Supersnug Puff™ Long, which has a slightly more feminine fit and is gorgeous if you wear a lot of winter skirts and dresses. But The Super Puff Long felt more in line with the look I was going for.
Sizing note: I went with a medium this time. I have I have The Super Puff₂o™ Mid in a small, and while it fits, I wanted to be sure to have plenty of layering room under this longer one.
Aritzia The Super Puff™ Long – cliMATTE™ in Black (M) // SOREL Out-N-About IV Chillz (8.5) // similar hoops
Alright! Let’s wrap this up! I wore this tried-and-true outfit to church on Sunday, and then out to lunch afterwards. Since I’ve photographed it before, I knew it would work. I could have worn black boots and belt and coat with this sweater and jeans, but I think the camel is a little more unexpected and fun.
Also, notice my Eagles green… Go Birds! (I tried my best, but I couldn’t seem to find any similar sweaters to link, at least not in anything close to this color.)
FYI, if you’re looking for a good budget-alternative to my MOTHER Weekenders in Wanted!, I’ve had a few people tell me these grey skinny flares from WHBM are a great pair of jeans with a very similar look. They also come in short and long lengths.
J.Crew Daphne in Hthr Camel (6) // Vince Raglan Turtleneck in Sea Onyx (M) // MOTHER Weekender in Wanted! (29) (budget option) // Veronica Beard Lisa in Hazelwood (8) (spend option / save option) // similar belt // similar gold hoops
I had a workout appointment on Monday, and I just stayed in my workout clothes for the rest of the day.
Side note: These Brooks Ghost Weatherized sneakers are perfect for outdoor winter workouts! They’re designed to be breathable while still providing warmth for cold-weather runs, and the water-resistant finish helps keep out snow and rain.
Athleta Altitude Fleece Lined Jacket (S) // Momentum Seamless Top (M) // Salutation Leggings (M) // Brooks Ghost Weatherized (9) // Jenny Bird earrings
Then yesterday, I pulled this outfit together for Bible Study. I had just talked about these jeans and this sweater in Monday’s Try-On Haul, so they were top of mind when I went to get dressed—and they ended up pairing really well!
For footwear, I first tried dark brown Chelsea boots (with a coordinating belt), but the heel wasn’t quite high enough for the length of these jeans. (That’s probably why I haven’t worn them much—I haven’t been able to wear high heels since I took that terrible fall last March.) So, I went back to my closet and grabbed these 3″ heels from last year. I wasn’t sure my feet would be able to handle them, but they did! I also swapped in a matching belt for a more cohesive look.
Style tip: I like to have a belt to coordinate with each color shoe in my closet—it makes outfit styling so much easier!
Equipment Madalene (S) // MOTHER The Hustler Roller Skimp (budget option) (29) // Veronica Beard Lada in Espresso – left (8.5) // Vince Hillside – right (8) // brown belt in dark brown – left (M) (option) // similar belt – right // similar gold hoops // Marlyn Schiff gold plated pyrite coin charm necklace & gold adjustable pull-chain necklace
I added my camel coat and a black scarf to finish the look. The black feels a little heavy against the rest of the outfit, but it seemed like the best option from what I have. Plus, I really needed a scarf since the V-neck coat and sweater left my neck and chest exposed to the elements.
J.Crew Daphne in Hthr Camel (6) // black scarf // MOTHER The Hustler Roller Skimp (option) (29) // Vince Hillside (8) // similar hoops // LV Neverfull MM
One morning in 3″ heels was all my feet could take, so I changed into comfy clothes for the rest of the afternoon.
Gap Factory Relaxed Fleece Half-Zip Sweatshirt (M) // old Athleta yoga pants // On Cloud 5 Running Shoe (9)
And that’s a wrap! Hopefully, this gives you some styling inspiration or ideas for mixing pieces in your own wardrobe. Let me know which look was your favorite!
Stay In Touch
If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.
I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a friendly place to discuss all matters of fashion and style with other women, share your outfits, get advice, and stay up to date on all the happenings in our community.