2025 Most Worn: My Favorite Finds of the Season

At the end of each year, I love looking back at the pieces I reached for most throughout the season. Since we’re in winter, I’m focusing on the fall and winter items I’m still wearing now—and will continue to wear through the colder months. In this post, I’m sharing a mix of the pieces that truly got the most wear in my closet.

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2025 Most Worn: My Favorite Finds of the Season

My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.

Wide-Leg Jeans

There were four pairs of jeans I found myself reaching for on repeat this season—all wide-leg or relaxed straight styles. My top pick overall is the Madewell Wide-Leg Jean. I can wear this style in both petite and standard, depending on the length. The standard has a 10.75″ rise and a 29″ inseam, while the petite has a 10.5″ rise and a 27″ inseam. I’ve found they shrink slightly in the wash over time, so the petite ends up a bit short for me unless I’m diligent about laying them flat to dry. Because of that, the standard length has become my go-to. They work well with boots, and after a few washes and dries, I can comfortably wear them with flats too.

Next are the Perfect Vintage Wide-Leg Jeans from Madewell in the Pipestone wash. These were a top seller this season and one of my personal favorites. They’re made from stretch denim and have a waist-cinching 10.5″ rise with a 28″ inseam in petite. I’m highlighting the Perfect Vintage Wide-Leg in this outfit, but I mixed in the other styles throughout the outfits in this series.

Finally, I really loved the Bella Wide-Leg and Relaxed Straight jeans from Quince. Both styles are made from stretch denim and have a 10.5″ rise with a 28″ inseam, making them easy, comfortable options for everyday wear. Plus at $50, they’re a great price. The 10.5″ rise doesn’t cinch at my waist as much as the PV Wide-Leg, but they’re very similar and half the price.

2025 most worn finds for fall and winter | winter favorites from petite fashion blogger Brooke of Pumps and Push-Ups

Jeans Petite 24 pipestone wash | Turtleneck XS | Sweater XS | Boots tts | Earrings

Petite-Friendly Knee-High Boots

When it comes to wearing dresses this fall and winter, I’ve been pairing them with my Sylvia Boots from Sam Edelman. I didn’t find many petite-friendly knee-high boots this season—only three stood out—and this pair quickly became my favorite. The Sylvia Boots have a 15″ shaft in a size 5, with the shaft height increasing as sizes go up, which is worth keeping in mind. I found the suede version much easier to wear since it’s soft and flexible, while the leather option hit the back of my leg and felt uncomfortable for extended wear. You can find more knee-high boots for petites in this post.

Dress Petite 0 | Boots tts | Coat Petite XXS | Scarf | Earrings

Spanx Booty Boost 7/8 Leggings

Over the years, I’ve found plenty of petite-friendly leggings from brands like Athleta, Aerie, and Gap, but this season I reached for my Spanx Booty Boost Leggings the most. The 7/8 length hits as a true full length on me, with a snug ankle fit and no loose hem. I gravitate toward these because of the combination of hold and comfort—they offer shaping and lift, have no front center seam, and still feel comfortable enough for all-day wear. For reference, I wear them in an XS.

My favorite leggings for 2025, the Spanx Booty Boost Leggings | petite-friendly leggings

Gola Elan Sneakers

Colored suede sneakers were a big trend this season, and I wanted to give it a try. I found Adidas styles ran too large for me, and while kids’ sizing can sometimes work, I had trouble finding an in-stock pair in a color I liked. I eventually found the perfect option in the Gola Elan Sneakers in a neutral shade. Bright, bold colors aren’t my style, so this soft bone color felt like just the right amount of trend for me. I wore these shoes heavily throughout the season and look forward to wearing them even more. They’re true to size—I wear a size 5—and they’re both comfortable and easy to walk in.

J.Crew Stevie Boots

A low-heeled boot with an elongated toe was the silhouette of the season. Whether you prefer a pointed toe, a softly squared shape, or a kitten or low chunky heel, this style feels both current and wearable. My personal favorite this season was the J.Crew Stevie Boots. I love the overall shape and color, and they’re easy to walk in and wear all day. They start at a size 5 and run true to size. If you’re looking for more boots, here is a post I reviewed a few different styles.