A J.Jill Try-On Haul: Winter Essentials You’ll Love for 2024

As the new year unfolds, it’s the perfect time to update your wardrobe with versatile, stylish pieces that blend comfort and elegance. Recently, I stopped by J.Jill to try on some of their newest arrivals, and I couldn’t wait to share my finds with you. I’m sharing my top picks from J.Jill, along with my assistant Megan’s favorites. Whether you’re looking for casual everyday outfits or layering pieces for winter, this roundup has you covered. Now, let’s talk about the details of these versatile and chic pieces.

For sizing reference, I am 5’6″ tall and usually wear a size M/L in tops and an 8 in bottoms. Megan is 5’10” and usually wears a large in tops and a size 14 in bottoms.

High-Rise Angled-Pocket Wide-Leg Jeans & Multiyarn Textured Pullover

This outfit strikes the perfect balance between casual and polished, making it an effortless choice for everyday wear. The soft pink sweater adds a pop of cheerful color, while the wide-leg jeans bring a relaxed, modern vibe. Together, the pieces create a look that’s comfortable yet stylish, perfect for everything from running errands to grabbing lunch with friends. The neutral-toned loafers subtly tie the outfit together for a cohesive and approachable style.

This cozy pullover sweater features mixed yarns for a unique textured look. It’s soft, comfortable, and easy to pair with jeans or leggings for a casual-chic vibe. I added Wide-leg jeans, which are having a moment. These high-rise angled-pocket jeans from J.Jill are comfortable and fit like a dream! Paired with the multiyarn textured pullover, this look is all about comfort with a touch of chic. The soft sweater adds dimension to the outfit, making it perfect for chilly days.

Textured Open-Front Cardigan & Striped Button-Front Shirt

This outfit is a fresh take on laid-back sophistication. The bright blue cardigan adds a cheerful, vibrant touch, perfectly balancing the classic vibe of the striped shirt underneath. Paired with relaxed-fit jeans and comfy loafers, this look is easygoing yet polished—a great choice for running errands or enjoying a casual day out while feeling put-together. It’s an outfit that says you’re ready for whatever the day brings, without sacrificing comfort or style.

This classic striped button-up is a versatile wardrobe essential that can be dressed up with slacks or worn casually with jeans. The lightweight fabric and single pocket detail make it both functional and stylish. I added the open-front cardigan in a stunning blue, which layers beautifully over the classic one-pocket button-front shirt. The cozy cardigan is the perfect layering piece with its open-front design and textured knit that adds a touch of elegance to any outfit. Ideal for transitioning between seasons, it’s a must-have for chilly days. I love the look of the two items worn together!

Pure Jill Mixed Yarn Pullover Sweater with Knit Wide-Leg Jeans

This outfit is the perfect blend of cozy and casual. The sweater adds warmth and a touch of visual interest, making it ideal for cooler days. Paired with wide-leg jeans, the look feels relaxed yet put-together, striking a balance between comfort and style. This ensemble is great for running errands or catching up with friends over coffee.

Add dimension to your wardrobe with this textured pullover that combines a soft knit with a relaxed fit. It’s a stylish yet comfortable option for cooler weather.

The wide-leg jeans offer a flattering high-rise fit with angled pockets for a modern twist. The soft denim fabric provides comfort and style, making them perfect for casual and polished looks.

Double-Breasted Cabled Cardi & Boyfriend Jeans

This outfit is a classic take on cozy, nautical-inspired style. The striped tee peeking out from under the textured cream cardigan adds a playful touch, while the buttons elevate the look with a polished feel. Paired with wide-leg jeans, this ensemble strikes the perfect balance between timeless and trendy, making it a versatile choice for everything from casual weekends to coffee dates.

This double-breasted cabled cardi is a standout piece! The texture and gold buttons give it a sophisticated edge. I paired it with this easygoing boat-neck tee is a comfortable and stylish staple with a relaxed fit that’s great for layering or wearing solo. It’s a classic piece you’ll reach for year-round. I love the J. Jill Angled-Pocket Wide-Leg Jeans. They help to create a relaxed, laid-back look that’s perfect for weekends or casual outings.

Classic White Shirt with Pure Jill Curved-Hem Cabled Cardi

This outfit is all about classic, effortless style. The crisp white shirt pairs seamlessly with the relaxed-fit jeans for a timeless look that feels polished yet comfortable. The rolled cuffs and loafers add a touch of casual charm, making this an easy go-to for anything from errands to a casual lunch out. Classic, versatile, and undeniably chic!

A timeless piece every wardrobe needs, this crisp white button-up shirt is perfect for layering under sweaters or wearing on its own. Its tailored fit adds a polished touch to any look.

These relaxed-fit boyfriend jeans are as comfortable as they are chic, with a slightly slouchy style that pairs perfectly with casual tops or structured blazers. A great everyday denim option for any season. I love the color of the versatile slip-ons, which feature a minimalist design with a cushioned footbed for all-day comfort. Perfect for casual outings or travel, they add effortless style to any outfit.

The cardigan adds a cozy yet refined touch, while the shirt keeps the look fresh and timeless. It features a curved hem for a flattering fit and a comfy design that’s ideal for layering. 

Fringed Exploded Floral Scarf

Accessories can elevate any outfit, and this fringed, exploded floral scarf is no exception. Paired with the white button-up shirt and curved cardi, it adds a pop of print and a touch of elegance. This combo is ideal for layering as we transition between seasons.

Soft Voile Shirred Top with High-Rise Angled-Pocket Wide-Leg Jeans

The Soft Voile Shirred Top is lightweight and breezy, perfect for layering or wearing on its own. The Wide-Leg Knit Jeans are the ultimate blend of comfort and style, with a soft knit fabric and relaxed fit. Perfect for lounging or running errands in style. Together, they create a comfortable yet stylish outfit that’s easy to dress up or down.

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Verse Of The Day

Matthew 18:20 (NIV)
²⁰ For where two or three gather in my name, there am I with them.”