J.Jill Fall Fashion for Women Over 50: New Sweaters, Jeans & Dresses

Gurls, I walked into J.Jill intending to try on a few of their new fall arrivals, and you can probably guess how that went. A few pieces turned into an armload of sweaters, jeans, and dresses headed straight for the dressing room. Lol!

J.Jill is one of those stores I’ve shopped at for years, so I have a pretty good idea of what to expect. Their clothing usually leans relaxed and comfortable, and their sizing can be generous. I don’t automatically grab my normal size because I’ve learned that sometimes a medium works, and sometimes I’m swimming in it.

That is one reason I like doing these try-ons for you. A website photo can tell us what something looks like on a model, but it doesn’t tell us how it hangs on a 5’6″ woman in her 60s, where the waist hits, how roomy the jeans feel, or if I’d actually want to wear it once I got home.

This fall collection has lots of warm browns, denim, and crimson, which you’ll see throughout this try-on. I also found several pieces that could be worn now and layered later when fall decides to actually show up.

Cotton Cashmere Polo With Relaxed Jeans

This was the first outfit I tried on, and that clove heather color immediately said fall to me. It is basically the color of every coffee drink people start ordering the minute September arrives. Lol!

I’m wearing a medium in the Cotton Cashmere Polo, and I liked the fit. It gives you the polish of a collared shirt, but it is much softer-looking than a traditional button-down. This would be an easy top to wear with jeans as I did here, but I could also see it with chocolate brown, cream, navy, or even a pair of dressier pants.

Here is a closer look at the sweater. The short sleeves make it especially useful during early fall when the calendar says sweater weather and the thermometer says otherwise.

The Pure Jill Bi-Stretch Denim 5-Pocket Jeans are also a medium. These fit me in a relaxed way. If you like your jeans loose and easy through the legs, you may love that. I tend to prefer a little more definition, so I would keep that in mind when choosing your size.

That is exactly why I tell you the size I’m wearing instead of simply saying something “fits true to size.” Two women can wear the same size and want completely different fits.

The Same Polo in Crimson

Same sweater, completely different look. The crimson is much more noticeable than the clove, and you gurls know I’m not exactly known for running away from color. Lol!

The Lightweight Tie-Waist Wide-Leg Jeans are a size 8. These are much fuller through the leg than the first pair and have the tie waist, so they create a completely different silhouette.

Wide-leg jeans aren’t going anywhere, but you don’t have to wear an exaggerated version to get the look. This pair gives you the wider shape while still looking wearable for everyday life.

This close-up gives you a better idea of the neckline and sleeve length. I’m still wearing the medium in the Cotton Cashmere Polo, so you can see that changing only the color makes quite a difference.

If I were choosing between the two colors, that would be tough. The clove is easier to mix with a fall wardrobe, but the crimson brightens your face and gives a simple jeans outfit some life. It came home with me!

A Simple Cotton Cashmere V-Neck Sweater

Now we’re speaking my language. A V-neck! The Cotton Cashmere Pullover Sweater is a small, which is not my usual size. However, the store didn’t have a medium in stock, so I tried the small, and it fit perfectly.

I paired it with the Authentic Fit Straight-Leg Jeans in a size 8. After cleaning out my own closet recently, I’ve gotten much pickier about jeans. I don’t need six pairs that all do almost the same thing. I want the pair that fits well, feels good, and fills a spot in my wardrobe. This is one that made the cut!

Straight-leg jeans are still one of the easiest styles to own because they work with almost every shoe in your closet, from sneakers and loafers to ankle boots.

The truffle color is a great fall neutral, and I like the simplicity of this sweater. Nothing fancy is happening here, but these are often the pieces we end up wearing the most.

I would wear this with jeans, olive pants, cream pants, or under a blazer or jacket later in the season.

A Cotton Midi Dress for Early Fall

This Cotton Midi Dress is a medium, and this one really feels like fall to me. The red background with the larger neutral floral print gives it plenty of color, but the brown and cream tones keep it from feeling too bright.

I also like the longer midi length. On my 5’6″ frame, it falls well below the knee and gives the dress a little more presence than the shorter styles.

The defined waist is flattering without feeling overly fitted, and of course, the pockets are always appreciated. Lol!

Here is a closer look at the print and the fit through the bodice. This is the kind of dress I could see wearing now with sandals, then later with a cardigan and a closed-toe shoe once the weather cools off.

Adding the Getaway Open-Front Long Cardi changes the entire outfit. The cardigan is a medium, and I really like the warm brown with the print. This is exactly how I would extend the life of a dress instead of deciding it can only be worn during one tiny window of the year.

Later, I would swap the sandals for a loafer or ankle boot and keep right on wearing it.

A Crimson Floral Dress

I’m wearing a medium in the Crepe Pintuck Dress, and the small print adds plenty of interest without getting so bold that you would tire of it quickly. The longer sleeves also help it transition into fall.

The length hits around my knee rather than being an especially long midi on my 5’6″ frame, so pay attention to the garment measurements if length is important to you.

Here is a better look at the print and the fit through the upper body. I like dresses like this because you don’t need to do much to them. Add shoes and a little jewelry, and you’re dressed.

Then I added the same cardigan. This is why a good neutral cardigan earns its keep.

I wouldn’t buy a cardigan just because it matches one outfit. I want it to work over several dresses, with jeans, and with pants I already own. This one passed that test during the try-on.

Pure Jill Double-Cloth Indigo Dress

Last is the Pure Jill Double-Cloth Indigo Dress in a medium. You know how much denim I wear, so an indigo dress was going to get my attention.

This has that simple Pure Jill look, and the darker indigo makes it easy to treat almost like a neutral. You could change its personality just by changing the accessories.

Right now, I have it with my Vionic sandals. Once the temperatures cool off, I’d add a cardigan or jacket and change the shoes.

The relaxed shape is going to appeal most to someone who doesn’t want a dress fitted through the waist or hips. That’s where knowing your own preferences matters.

A dress can be well made and comfortable and still not be the right dress for you. I try not to label everything I try on as fabulous simply because it is new. My closet cleanout cured me of that in a hurry. Lol!

What I Thought About This J.Jill Fall Collection

This try-on felt very J.Jill to me, but in a good way. There are plenty of relaxed pieces and neutrals, but the crimson gives the collection some color so everything doesn’t disappear into a sea of beige.

The pieces that stood out most to me were the cotton cashmere sweaters, the Cotton Midi Dress, and that long cardigan because I can immediately think of several ways to wear each of them.

And that’s something I’ve become much more conscious of lately. Before I buy something, I’m asking myself:

• Where would I wear it?
• What do I already own that works with it?
• Would I reach for it more than once or twice?

Those questions aren’t nearly as exciting as, “Oooooh, that’s cute!” But they make for a much better closet. Lol!

If you’re shopping J.Jill, also remember that their sizing can run generous depending on the style. In this try-on alone, I wore everything from a small to a medium in tops and dresses and a size 8 in several of the jeans. Use the individual garment measurements and reviews along with my sizing as a reference rather than assuming every piece will fit exactly the same.

If you’d like more ideas for building a wardrobe where your pieces actually work together, you might also like my 15 Fashions Women Over 50 Need In Their Closet.

So now I want to hear from you. Which piece would you take home from this J.Jill try-on? I’m curious if we’re all going to pick the same thing.