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

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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

Tania Stephens wearing a pink sweater with jeans from J.Jill
Multiyarn Textured Pullover (Small) | High-Rise Angled-Pocket Wide-Leg Jeans (Size 8) | Essa Slip-On (TTS)

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.

Tania Stephens wearing a pink sweater

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

Tania Stephens wearing a striped shirt, a blue cardigan, and trouser jeans from J.Jill
Striped Button Shirt (Small) | Textured Open-Front Cardi (Medium) | High-Rise Angled-Pocket Wide-Leg Jeans
(Size 8) | Essa Slip-On (TTS)

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.

Tania Stephens wearing a striped shirt and a blue cardigan

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

Megan is wearing a gray textured sweater and jeans from J.Jill
Mixed-Yarn Pullover Sweater (Large) | Wide-Leg Knit Jeans (Large)

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.

Megan is wearing a gray textured sweater  from J.Jill

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.

Megan is wearing trouser jeans from J.Jill

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

Megan is wearing a striped shirt, a double breasted cardigan, and trouser jeans from J.Jill
Relaxed Boat-Neck Tee (Large) | Double-Breasted Cabled Cardi (Large) | High-Rise Angled-Pocket Wide-Leg Jeans (Size 12)

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.

Megan is wearing a striped shirt and a double breasted cardigan from J.Jill

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

Tania Stephens wearing a white button down shirt with jeans from J.Jill
Classic White Shirt (Medium) | The Boyfriend Jean (Sisze 8) Essa Slip-On (TTS)

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!

Tania Stephens wearing a white button down shirt from J.Jill

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.

Tania Stephens wearing a white button down shirt, a blue cardigan, and  jeans from J.Jill
Classic White Shirt (Medium) | Curved-Hem Cabled Cardi (Medium) | The Boyfriend Jean (Sisze 8) | Essa Slip-On (TTS)

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.

Tania Stephens wearing a white button down shirt and a blue cardigan from J.Jill

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

Tania Stephens wearing a white button down shirt, a scarf, and a blue cardigan from J.Jill
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

Megan is wearing a blue top and trouser jeans from J.Jill
Soft Voile Shirred Top (Large) | Wide-Leg Knit Jeans (Large)

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.

I hope you enjoyed this J.Jill try-on haul as much as I enjoyed putting it together! These pieces are perfect for creating outfits that feel as good as they look. If you’re looking to refresh your wardrobe with comfortable yet stylish options, J.Jill is always a great place to start. Let me know which outfit is your favorite or if you’ve tried any of these pieces. Don’t forget to check out their current sales for some amazing deals!

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59 Comments

  1. Can you let us know again on what diet/fitness program you joined several years ago? I thought I wrote it down but I didn’t.

    1. I was doing E2M, and it was found on FaceBook.

  2. Those Essa shoes are perfect with every outfit I need those – thanks for sharing!

    1. I LOVE the fit and color. Plus, they are so comfortable.

  3. Tania do you know length of the boyfriend jeans? True to size or no?
    Cute options. Love the double breasted sweater !

    1. The jeans are 27″ when rolled, and Petite’s are 24″ rolled. They do run true to size.

  4. The Blue Cardi and the crisp White blouse are knock outs!! No matter what age it is so classic, I have the white blouse and gave one to my daughter-in-love this past Christmas and she loves it!!
    You look terrific as usual, I love J Jill, it’s right around the corner near me in Charlotte!!
    Bless!!

  5. Susan Weston says:

    Do the sleeves on the white shirt run short?

    1. No, I didn’t notice them being short.

  6. Roberta Schwandner says:

    I really like the multi colored and textured sweater.

  7. Jennifer Steadman says:

    Great finds- thanks for the recommendations.

  8. Kim in VA says:

    Thanks to you and Megan for the try-ons! I especially like the pink sweater on you and the cream cardi/striped shirt on Megan. J.Jill is my favorite store, and about a third of my wardrobe is J.Jill. I love that all of their clothing is offered in petite, and I love their sales. If possible, could you please show the waistbands and pockets of pants and jeans? It would be really helpful to see them with shirts tucked in, side and back views.

  9. Love the grey sweater. Appears nice and warm for the winter we are having

  10. Susan Radtke says:

    Love the grey sweaters.

  11. Love the try on blogs and the look at different sizes! Thank you for the try on haul, really cute items! Have a wonderful weekend!
    blessings,

  12. Susan Weston says:

    Nice selection! Pink sure looks good on you!

    1. Great outfits! I love them all.
      Barb

  13. Ginger Hiller says:

    I thoroughly enjoyed this post! Both of you tried on some very pretty pieces. I really like the stretch jeans and the pink marbled sweater you shared is beautiful. Maybe I will order something from JJill one of these days.

  14. I might get one of those snow joes

  15. I need a new white shirt! I love the double breasted cardigan Megan is wearing ♥️

  16. I hope Megan got the double breasted sweater and jeans! She looked great in that outfit. I loved several items from your try on! Thank you!

  17. Love the crisp white shirt, curved hem cardigan and scarf outfit and on Megan I love the nautical inspired outfit!

  18. Elizabeth says:

    Love seeing Tom again! To live the life of an indoor kitty. lol

  19. Those J.Jill pullover sweaters are so pretty. Love the colors of both. Thanks for going to J.Jill for this try-on haul. It’s my favorite place to shop!

  20. Those are great styles. I’m in need of a white button down blouse – that looks like a well made and classic choice. I’ll have to look into getting one!

  21. Melinda Thompson says:

    Thank you for featuring Jjill on this try on post. My favorite so far this year. Headed to their website now…..

  22. love Jill! it’s fun to see two body types trying on the outfits.

  23. Love the pull-on sweaters. And, as always, your try on blogs are great.

  24. Marsha Ebersole says:

    Love seeing both sizes. Beautiful clothes and beautiful models.
    Marsha Ebersole

  25. sue koren says:

    All of these outfits are so pretty!

  26. Dottie W. says:

    Hi Tania! Just wanted you to know that you have the best ideas outside of fashion as well. The Snow Joe snow thrower – I never even heard of it before and I ordered one right away. I’m 73 and my hubby is handicapped and can’t help. A shovel takes forever even for a small amount of snow. Can’t wait to get this. Also, the modern looking head phone/ear pods that you showed last month were awesome! My son cycles and I also worried about him not hearing what was going on around him with ear buds in. He loves these. Thanks so much for sharing these lifestyle items with us!

    1. Dottie, I’m so glad you are finding the blog so helpful! I love sharing all the finds that I like and use.

  27. I really like the pink sweater you are wearing and the white shirt with the cardigan and scarf. Those really look nice on you.
    I like the textured sweater and double breasted cardigan with the striped tee Megan has on. I wouldn’t have thought to put the tee with that cardigan but it looks really cute!
    We’ve had about 13 inches of snow here. It’s probably been about 10 + years since we’ve had that much snow so I guess we were due. ⛄️

  28. J.Jill can be so hit or miss for me , but lately I have loved so much!!! Everything you girls highlighted looked great! I especially loved the scarf you added to the cardigan! Happy Saturday ❤️❤️❤️

  29. I like the wide leg jeans. The angled pockets are more slimming than little patch pockets in front. I’ve decided I’m not buying anymore pants or jeans with little front patch pockets because they emphasize your tummy if it’s not flat. The jeans look good on both of you. I like the cardigan with the gold buttons too.

  30. Gayle Davis says:

    Love the gray cardigan! So many possibilities with it.

  31. Bridget Wilson says:

    I always love your J jill try on!

  32. Gay Craig says:

    Love the shoes! They look comfortable

  33. J Jill is my favorite store. I love the white blouse, curved hem cardigan and beautiful scarf! I love their high rise straight leg jeans. I find I need to size down when I purchase from J Jill. Thank you for the new options. They look great:).

  34. Julie Feagins says:

    Enjoyed the try-on haul! It’s great to see two women, different body types, in clothing at a retailer. Great perspective!
    Keep up the good work!

  35. I am loving J Jill clothes again because of your try-on hauls! Thanks

  36. Roberta Schwandner says:

    I like the cardigans.

  37. Thank you Tanya! I love J Jill! Was just shopping there yesterday!

  38. Janelle Bracken says:

    Hi, Tania! I really enjoyed this try-on haul at JJill! Thank you so much for all of the effort you (and Megan!) put into these to give us all of the details!

    Love the JJill Classic White Shirt you have on, and the blue/white striped one, too! I discovered the white shirt last fall and ended up buying two of them! I can add that both of mine have washed and worn well, and do not wrinkle much at all. I hang mine up on a hanger out of the washer and let them air dry. (Who has time to iron much anymore?) Anyway, besides looking great under so many things, it’s ready to wear again easily. Take care and stay warm while we all dream of warmer weather! 😁

    1. Janelle, I should have had you write my post! You did a great review of the classic white shirt, and you are exactly correct. I have two of them, and they are the one I reach for the most often.

  39. The cardigans are my favorite.

  40. Grandma Judy says:

    J Jill is one of my favorite stores. I love all of the outfits you tried on but Megan especially looks great in her outfits. I think she has found her go to store.

  41. Love J Jill! Great outfits!

  42. Looks like fun, I’m snowed in! Great pieces.

  43. Very cute double breasted cable sweater.

  44. Kathy Dolan says:

    Love these try on hauls. Really give a perspective since mostly online shopping. Appreciate you two doing this!

  45. Love the double breasted cardigan with the stripe tee! 😍

  46. Double breasted cardigan is beautiful.

    Not a fan of this weather!

  47. Cammie Bruce says:

    But it is 2025! Lol, Happy New Year!

  48. Great pieces. We don’t have a J Jill locally, reminds me of Talbots.

  49. Kathy Laweryson says:

    I don’t remember hearing about J Jill, you’re broadening my horizons, Tania! I really love that pink sweater on you and the double button sweater on Megan!

  50. I like the knit jeans!

  51. Ruby Hostetler says:

    snowing here as well i love when the ground is covered with snow. its so much better than rain and mud in the winter. RAH