Yes, I know…two dressing room try-ons in one week. But when I tried on some of J.Jill’s Fall 2025 collection this August, I knew I couldn’t risk waiting. They have a habit of quietly changing their links, and then we’re both left wondering if that perfect cardigan was a figment of my imagination. This J.Jill Fall 2025 dressing room try-on for women over 60 is less about padding my own closet and more about giving you a peek at what’s new and what’s worth a second look.
If you’re new here, welcome. A try-on is when I head into a store and style pieces from the latest collection so you can see how they look on a woman over 50. I share sizing tips and ideas for how to wear them. For reference, I’m 5’4″, on the cusp of petite, with broad shoulders and straight hips. J.Jill carries regular, petite, and tall, in sizes XS–4X. I usually start in petite but shop all sections for the best fit.
Soft Black Denim Skirt with a Denim Shirt — Minus the Texas Tuxedo Vibe
I love the double denim look, and this pairing won’t make you feel like you’re headed to a rodeo. This Pure Jill washed black denim knit skirt is a soft cotton blend with a hint of spandex, giving it just enough stretch to move with you. It feels like yoga pants pretending to be a skirt…comfortable, forgiving, and polished enough for dinner out. The fabric is smooth, not stiff, and would dress up or down easily.
I paired it with J.Jill’s deep-wash denim shirt in a smooth, mid-weight cotton that’s surprisingly soft right off the hanger. The darker blue works perfectly with the washed black, so it feels deliberate …not like you grabbed mismatched denim on laundry day. I love this denim shirt, but I already have a similar one, so I didn’t buy it.
Right now, I’d roll the shirt sleeves and wear it with flats or sandals. Come cooler weather, layer a sweater jacket over the shirt, add ankle boots, and you’ve got a cozy double-denim look that doesn’t feel like a costume.
Lightweight Cardigan and Wide-Leg Ankle Jeans That Don’t Swallow You Whole
Next up, I tried J.Jill’s Wearever Soft Open Cardigan…a lightweight cotton blend with just a whisper of stretch, smooth to the touch, and thin enough to drape without clinging. The 3/4 sleeves and hip-length cut (I’m in a size small regular here) keep it from looking boxy, and it comes in petite, regular, and tall.
The wide-leg ankle jeans are mid-weight denim with a soft, broken-in feel right off the hanger. I’m wearing a small regular, which hits just above my ankle at 5’4″. The fabric holds its shape but still moves with you, looking relaxed without sliding into sloppy.
Wear this outfit now over a pima stretch tank and sandals, then swap in a long-sleeve tee and ankle boots when the weather cools.
Two White Shirts, Two Different Vibes
ON RIGHT – NO-IRON A-LINE TUNIC SHIRT size S / COTTON STRETCH CUFFED PANTS size S
White shirts are everywhere this season, but J.Jill’s August arrivals offer two distinct options…each shown here with a different pair of pants.
On the left, the popover top has a placket front and a straight shape. It’s made from a smooth, mid-weight cotton that holds its shape. I paired it with the slim ankle jeans in a curvy fit, which have more room through the hips and thighs than my straighter shape needs… plus they are one size too large for me…so they look sloppy. Trust me, these are great jeans.
On the right, the no-iron A-line tunic has extra length and a softer drape that falls away from the body, which is a great choice if you like more coverage at the waist or want something that works well over leggings. It’s shown here with the cotton stretch cuffed pants in a size small regular. The pants are lightweight with a soft, smooth finish and a bit of stretch for comfort.
The Soft Flattering Tee I Couldn’t Leave Behind
Part of J.Jill’s August fall 2025 arrivals, this Pima slub elbow-sleeve tee rang a lot of bells for me… primarily the color, the set-in sleeves, the soft fabric, and the V-neckline — so it came home with me. It makes me wonder how much I would love my wardrobe if everything I bought rang all those bells! The fabric has a subtle slub texture that keeps it from looking flat, and it’s very soft.
I paired it with these Wearever Classic Smooth-Fit Slim-Leg Pants, also new for fall. The rayon-nylon blend has 13% spandex, so they move like leggings but keep their shape all day. These are navy and they also come in black.
A Gorgeous Green Midi Skirt for Fall
This Pima 3/4-sleeve V-neck tee is one of those quiet basics you end up reaching for far more often than you expect. The cotton is soft, smooth, and light enough to layer under jackets without bunching. It comes in 6 colors plus a polka dot.
I paired it with J.Jill’s slit-back denim midi skirt in Adriatic Sea…a deep greenish teal, I’m particularly fond of. Gorgeous greens are showing up all over the place for fall 2025, and this one feels rich without being overpowering. It also comes in a fun cheetah print or a gorgeous medium blue denim wash. It has just enough spandex to be comfy and move with you instead of holding you hostage. The back slit makes it walkable while keeping the look streamlined. I’m really hoping they’ll bring out more items in this color.
Soft, Striped, and Ready for Fall From the J.Jill Fit Collection
This navy-and-white textured striped pullover from J.Jill’s Fit Collection is softer than you’d expect from something with this much texture. The cotton blend feels smooth against the skin, and the medium weight makes it easy to wear now or layer later.
I can easily see this worn with a pair of white jeans now, deep navy pants later, or with leggings for heading to the gym. There’s also a coordinating striped skirt, which would make an elevated casual look, worn with white tennies.
The leggings are soft, totally opaque, and very stretchy. I always size up in leggings because I hate that “spray-painted” look. These are navy, and they also come in black or white, reg, petite, or tall. I’m wearing a regular, and it isn’t cropped on me…which I prefer because it elongates the look of my short legs.
An Easy Cardigan in Fall’s Soft Green
Another great soft green for fall, this time in an easy-to-toss-on cardigan. This softly textured cardigan is lightweight but not flimsy, with a slightly nubby texture that makes it feel more interesting than a plain solid. It’s a nice length to wear over longer shirts like this tunic shirt.
That’s everything I tried on this trip…a mix of easy layers and polished basics that feel very wearable. As always, some pieces spoke louder than others, but it’s nice to see a fall lineup with fabrics that feel good and cuts that work in real life.
Have you spotted any favorites from J.Jill’s fall 2025 collection? I’d love to know which ones you’d take into the fitting room, and which you’d leave on the rack.