My Most Worn Pieces of 2025 (Shoes, Denim & Staples I Loved)

And with that…the 2025 season comes to an end. 2025 felt like the longest decade of my life (I heard someone say that the other day and it feels so true). But, as always, I’m trying to focus on the positives in the new year and this ‘Most Worn Pieces of 2025’ series on TME (see Shana’s here) has been so much fun to scroll back through 2025 and reminisce on all the good, the bad and the (maybe?) ugly fashion choices I made in 2025.

Thankfully, there were more wins than losses. For example, 2025 can go down as the year I discovered the Adidas Samba Janes and my life was never the same. Okay, maybe that’s being tad dramatic, but my daily style this year was definitely not the same after them. And we can count that as a big win for 2025. In fact, there were several big wins, fashion-wise for me this year.

My Most Worn Pieces of 2025

Sweater (M) | Pants (27) | Timberland Boots (7.5)

It was a solid year for me, fav-finds-wise. And I discovered several new and life-changing (again, dramatic much, Jess??) footwear: hello, Laidback London Boots, where have you been my whole life? and lots of other wardrobe staples like that Gap Oversized 100% Cable-knit sweater that I just can’t stop yapping about that keeps selling out and the Free People boyfriend jeans I love so much that I bought in two versions! And I can’t forget about the Timberland Stone Street Boots that helped me level-up my everyday style in a big way this fall and winter. I loved seeing what worked for me and loved even more seeing what worked for everyone else on the TME team. Onwards and upwards friends, and as always thank you so much for following along on the journey!

01 | Adidas Samba Janes

The first spot on my list of most-worn pieces of 2025 easily goes to: the Samba Mary Jane. It wouldn’t be inaccurate to sum up my style in 2025 as ‘The Year of the Samba Jane’s’ (plus a few other essential pieces, obviously). Pick a day in 2025, and chances are I was wearing these bad boys and loving life. I mean, they are just so darn comfy and easy to wear. Not to mention that they go with almost everything I own. Score!

Jacket (S) | Pants (27) | Shoes (7.5)

These Sambas are not-so-quietly my most-worn shoes of the year (especially in spring and summer). With a classic silhouette that blends sporty cool with everyday wearability, they elevate everything from dresses to jeans without skipping a beat. Whether I am running errands, traveling, or grabbing coffee they deliver comfort and style in equal measure, making them a true year-round essential.

Sh o es (7.5)

Where to Buy Adidas Samba Janes

Nordstrom | Adidas | Foot Locker

Fit Notes: I found that these Samba Janes run a little wide, but luckily the velcro strap helps negate that very well. Many readers found them to run large but I have been happy with my usual 7.5 size. They are designed with an extended topline curving down to the traditional T-toe. They have a grippy, gum-rubber sole, a leather upper, with a synthetic lining. They have an adjustable hook-and-loop velcro strap and have a removable, cushioned insole.

02 | Gap 100% Oversized Cable Knit Sweater

If you’ve followed any of my posts this year, this sweater should come as no surprise. I love to talk about it any chance I can get. I have it in both the navy and cream versions (and I am wearing my navy option as I’m typing this). I also gifted one to both my mother-in-law and sister-in-law, and they’re already big fans too.

Sweater (L) | Jeans (27) | Boots (7)

What makes this sweater so good is: the quality. Gap did not skimp on the quality with this 100% cotton sweater. It feels like old-school, high-quality, medium-weight knit but with ZERO itchiness. It is also breathable, slightly oversized and easy to wash. My sweaters have been in the wash multiple times already and they look good as new, I just lay them flat to dry.

Fit Notes: This cable knit sweater is made from 100% cotton and fits slightly oversized so there is no need to order a size up. Unfortunately, this sweater sells out SO FAST but don’t worry, I am constantly refreshing Gap’s website and they have been really good about restocking often, so keep checking back here and I will link to the women’s version as soon as it is restocked but for now, the men’s version is just as good, it just fits slightly less oversized.

03 | Timberland Stone Street Platform Hiking Boots

If one thing stayed true for me in 2025 (and the previous decade) is that my love of a high-quality, brown, leather chunky-sole boot. Last year I discovered Doc Marten’s Leona Boots and I still wear those a couple times a week in the winter but I have added these gorgeous Timberland Stone Street Platform Hiking Boots to my winter leather boot rotation after drooling over them for years.

Sweater (M) | Pants (27) | Timberland Boots (7.5)

These boots consistently take my breath away. The unique detailing, the rich burgundy brown coloring, the leather shoestrings, and side leather stitching, plus the durable chunky sole are just absolutely top-notch. Plus, I’ve been wearing them all winter long, through several blizzards now and they still look brand new. They really are just. THAT. GOOD.

Timberland Boots (7.5)

Fit Notes: These boots run true to size and also come in a ‘dark blue’ leather option and a lighter ‘wheat grain’ leather option as well. They have a 1 1/2″ chunky, rugged platform sole that works for hiking the hills or the city’s streets. They feature a lace-up style, an OrthoLite® footbed, and a leather upper/ReBOTL textile lining/rubber sole. Also, they are sustainably made with one or more components consisting of ReBOTL material that contains at least 40% recycled plastic from post-consumer plastic bottles.

04 | Free People Deep Trance Jeans and Corduroy Pants

I’m sensing a theme to my style…if I love something, I have no shame in buying similar versions or multiples of the same items. And that is exactly what happened with these Free People Deep Trance Jeans. Gimme all the versions of these jeans in 2026, K. Thanks.

Similar Cardigan (S) | Corduroy Pants (27) | Similar Clogs (7.5)

I first discovered the denim boyfriend version and wore them all.summer.long. You can even watch a YouTube video of 11 different spring and summer transitional outfit ideas featuring the denim version of these favorite jeans of mine. Luckily, there are several different variations to these jeans so I can buy as many as my heart desires.

Fit Notes: These jeans are 70% cotton, 22% modal and 2% elastane (so they have a decent amount of stretch). They have a 25″ inseam, an 11 1/2″ front rise, and 15″ back rise with a button fly. They run TTS, but if you run in between sizes like me, I would size up. They are comfortable enough for everyday wear yet structured enough to feel intentional. The corduroy version runs true to size, and the denim version runs large, so order one size down.

05 | Levi’s Baggy Dad High-Waist Jeans

These Levi’s Baggy Dad Jeans in Rebel Edge Black instantly filled a gap in my denim lineup with a more current, fashion-forward black silhouette. They’re the effortlessly cool pair I keep reaching for lately. The softly faded black wash adds just the right amount of edge, while the relaxed, drapey leg creates the perfect contrast when styled with a bold statement piece—like a bright red, ultra-soft cardigan and the Western Bubble Shortie Jacket. The result feels dramatic and elevated without relying on sequins or sparkle.

Puffer Jacket (S) | Cardigan (S) | Jeans (27) | Flats (7.5)

Where to Buy Levi’s Baggy Dad High-Waist Jeans

Levi’s | Nordstrom | Bloomingdale’s | Shopbop

Fit Notes: These jeans fit a little tighter in the waist than I was expecting, I definitely would suggest ordering a size up, especially if you are looking for a more relaxed, baggy fit. I went with my regular 27 here, but would gladly exchange for a 28. These jeans come in different great color options, are loose through the leg and hip, feature a tapered ankle, and a mid-rise (which on me, felt more like a high-rise since my jeans were a tad too small). They are made from 100% cotton, twill, and are non-stretch. They have a zip fly, and 5-pocket styling.

06 | Mango’s Picarol Double Breasted Wool Blend Coat

Living in Michigan means I have all the coats: the puffers, the rain jackets, the quilted jackets BUT what my winter wardrobe has been sorely lacking was chic, classic, black wool coat. And as luck would have it, I found my dream black double-breasted wool blend coat at Mango of all places.

Coat (S) | Asymmetrical Blouse (S) | Jeans (27) | Bag | Heels (7.5)

I love the simplistic and timeless style of this coat and I have been wearing it all winter long. Also, the price tag is quite reasonably affordable for such great quality and cut. It fits and looks like a much more expensive coat and we loved it so much we also gifted one to my sister-in-law who lives in Chicago.

Fit Notes: This coat runs large, order one size down. This is one of those coats that instantly makes every outfit look intentional and put together. The relaxed, oversized fit hangs beautifully without any unwanted bulk, and the slightly dropped shoulders add just the right hint of modern ease. And because it’s handmade, the wool feels soft yet substantial. It’s warm enough for chilly mornings but still light and roomy enough for layering – I could even see myself keeping it on indoors.

07 | Honorable Mention for 2026: Laidback London Boots

I have been seeing Laidback London Boots online for the last couple of years and they have always looked ‘oh-so-cozy.’ But, I have Abby and Shana to thank for me finally pulling the trigger and purchasing the boots and I am forever indebted to them for introducing me to my new favorite cozy/everyday boots that I’ve barely wanted to take off since they arrived.

Laidback London Boots (7.5)

Think: warm hugs but for your feet. These booties are the best thing I’ve put on my feet since my first pair of Mou boots. And, I can’t believe I’m saying this, but these might even overtake my Mou boots for my favorite boots simply because they have a more fitted, slimmer opening with a zipper that keeps these boots a tad more secure than Mou boots.

Boots (7.5) | Red Puffer (S) | Sweater (S) | Jeans (27) | Boots (7.5)

Fit Notes: These boots run pretty true to size and work with or without socks. They do stretch out a little over time, so if you are between sizes, order half a size down. This ankle boot is made with a lugged outsole, a genuine-shearling lining and a durable suede upper with hand-stitched details, a side zip closure and a removable, cushioned insole with arch support.

p.s. How cute is my mama who visited me for Christmas??

As always, thank you so, SO much for reading and being with my on this style journey through the years. I have so loved being part of this wonderful TME community and look forward to what the new year brings us all. Until next time,

xo, Jess ( My Instagram | More of My Posts )

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