J.Jill Try-On for Women Over 50: What Worked (And What Didn’t)

I’ve tried on enough clothes over the years to know that not every brand is designed with us in mind. Some lines lean stiff, and some skew overly trendy. And some assume we all want cropped and fitted in places we don’t.

J.Jill has always felt a little different to me. I’ve been trying on their pieces for years, and I’ve learned that what looks relaxed on the hanger doesn’t always behave the same once you put it on. The real test is how it skims, how it moves, and how it feels after sitting, driving, and actually living in it.

And I’ve also learned this. J.Jill runs generous. I’m usually between a medium and a large, but here I’m often between a small and a medium. So this try-on isn’t just about what’s new. It’s about what works, what doesn’t, and what I’d size differently after standing in the dressing room long enough to know better.

• BTW – The 30% Off All Sweaters, Tees, Shirts & More ends today. The discount shows once in the cart.

When a Basic Top Just Isn’t Enough

There are days when a t-shirt just feels too casual, but you don’t want to pull out something stiff or overly dressy either. That’s where this Paisley Satin Top fits in.

The fabric has a soft sheen, so it instantly looks nicer than cotton, but it doesn’t feel precious. You could wear this to lunch, church, or dinner out and not feel overdressed. It elevates regular jeans without asking you to change your shoes or add ten accessories.

Now let me tell you what I noticed. In the small, it was slightly snug through the chest. Not tight enough to panic, but enough that I knew I would be adjusting it if I kept it. And I’ve learned over time that if I’m aware of a pull in the dressing room, I’ll be aware of it all day. I would size up to the medium next time.

The Straight-Leg Ankle Jeans are the steady piece here. They aren’t skinny, they aren’t exaggerated, and they don’t compete with the top. They just balance everything out. When you want to look a little more polished without feeling like you’re trying, this combination makes sense.

If You’re Tired of Defaulting to a Plain Tee

I think a lot of us fall into the habit of reaching for the same basic top over and over. I know it is easy, safe, and works. But sometimes you want something with a little personality without jumping straight into bold or busy.

This Pure Jill Border-Printed Top does that quietly. The placement of the print gives it shape, so it doesn’t look boxy or oversized, which can happen with relaxed cuts. In the small, it skimmed without swallowing me, and that balance is important. I don’t mind ease, but I don’t want to feel hidden inside my clothes.

It’s still comfortable. It still feels like something you could wear all day. But it looks like you made a decision instead of grabbing whatever was closest.

And sometimes that small upgrade is all you need.

A Simple Sweater That Feels Like Spring

There’s a difference between a sweater that looks cozy and one that actually feels wearable. Some of them look great on the hanger, and then the minute you put them on, they add bulk in places you weren’t trying to add bulk. This one didn’t do that.

This Relaxed Pullover Sweater is lightweight enough that it doesn’t sit heavily across the chest or upper arms, which is usually where I notice extra fabric first. The small gave me that relaxed look without turning into oversized, and with J.Jill sweaters, that balance matters. They tend to run generous, so unless you want it intentionally slouchy, you may find yourself sizing down.

I liked that it didn’t require fussing. I didn’t feel the need to front-tuck it or adjust the hemline to make it work. It just sat the way it was supposed to sit. The Straight-Leg Ankle Jeans looked great with all three looks.

This is the kind of sweater I would keep in rotation for those in-between days when it’s cool in the morning and warm by afternoon. It feels soft and easy, but it doesn’t look like you grabbed a sweatshirt.

Neutral Linen That Doesn’t Feel Frumpy

Linen can go one of two ways after 50. It can look relaxed and intentional… or it can look like you gave up halfway through getting dressed.

I was surprised when I tried on these Linen-Blend Wide-Leg Pants. Wide-leg and linen together can feel like a risky combination, especially if you’re not trying to add volume through your hips. But these fall straight down from the waist instead of flaring out dramatically. They don’t grab through the thigh, and they don’t outline anything I’d rather not highlight. They move when you walk, which keeps them from feeling stiff.

And yes, linen wrinkles. It always will. But there’s a difference between sharp creases that make you look rumpled and soft wrinkles that just look lived in. These fall into the second category.

I stayed in the small because J.Jill runs generous, and I didn’t want extra fabric through the waist. If you’re between sizes, you may find yourself sizing down in their bottoms.

Now let’s talk about the Open-Texture Cardigan, because this is what makes the outfit feel intentional instead of plain.

Cream can sometimes fade into the background, but the open texture on this one gives it personality. It isn’t just a basic neutral layer. The detail makes it interesting without being busy, which means you can wear it with almost anything in your closet, and it still feels like you made an effort. I went with the medium because I like a little breathing room in layers, especially through the arms.

This is the kind of outfit that works when you want to look pulled together but not overdressed. You could wear this to lunch, to church, or even traveling, and never feel like you’re tugging at it or adjusting it every five minutes.

It’s relaxed, but it doesn’t look frumpy.

An Outfit That Feels Relaxed Without Looking Sloppy

Lightweight cotton can sometimes look thin or flimsy, especially in lighter colors. I always check that first. I don’t want to feel like I need a cami, a tank, and a prayer just to leave the house.

This Voile Top is airy without being sheer, and the shirring gives it shape so it doesn’t hang straight down like a box. In the small, it skimmed comfortably without pulling across the chest or shoulders.

Paired with the Linen-Blend Pants, this outfit feels easy yet still looks put together. It’s comfortable enough to sit in for hours, but it doesn’t look like lounge clothes. That line can be tricky, and this stays on the right side of it.

I think sometimes we hear “relaxed fit” and assume it means shapeless. It doesn’t have to. When the fabric moves and the cut has some structure, relaxed can actually look very flattering.

A Button-Down That Doesn’t Feel Stiff

I’ll admit, I almost passed this Embroidered Button-Front Shirt by because I assumed it would feel rigid. Traditional button-downs can sometimes pull across the chest or feel tight through the shoulders, and I’ve learned not to ignore that in the dressing room.

I sized up to a medium because I was preparing for that stiffness, and honestly, I didn’t need to.

It’s softer than it looks. The embroidery gives it detail without making it feel busy or overly youthful. I could have worn the small comfortably, which tells me the fabric has more give than I expected.

The pull-on Knit Jeans are what make this outfit practical. They look structured enough to pass for regular denim, but they move. I don’t like pants that feel restrictive when I sit down or drive, and these didn’t fight me.

This is one of those outfits I could see wearing on a regular weekday without thinking twice about it. Comfortable, but not careless.

The Poncho That Came Home With Me

I brought this Rose Petal Sweater Poncho home. And that usually tells you everything you need to know.

A poncho can go wrong fast. If it’s too short, it cuts you off in an awkward place. If it’s too tight, it defeats the whole purpose. I chose the M/L because I wanted the length and the volume. I don’t mind fabric as long as it drapes instead of sitting stiff, and this one drapes.

The soft pink is flattering without feeling sugary, and the shape feels forgiving without looking like I’m hiding. There’s a difference. I don’t want tight, but I also don’t want to disappear inside my clothes.

I wore a tank under the poncho since the arm holes are large. I plan on layering it with a button-up shirt or long-sleeve tee while the weather is still chilly.

The Trend I’m Still Thinking About

These Quilted Printed Jacket are everywhere right now. My 17-year-old granddaughter wears one constantly, and she makes it look effortless.

When I tried this one on, it fit well. The small worked, and it’s lightweight and easy to move in. I just haven’t decided if it feels like me.

And that’s something I’ve learned over time. I don’t buy something because it’s trending. I buy it because I can see myself reaching for it without second-guessing. This one didn’t give me that feeling right away.

That doesn’t mean it’s wrong. It just means I’m still thinking.

A Set That Feels Modern Without Trying

This one felt right as soon as I put it on. Sage is having a moment, but this deeper tone feels grounded instead of trendy. It doesn’t scream for attention; it just looks fresh.

The Button-Front Jacket was slightly snug through my shoulders in the small. I would probably size up to the medium for comfort, especially if layering underneath. I’ve learned not to ignore that slight tightness because it never gets better after washing.

The Linen-Blend Pants drape the same way the other linen pair did, relaxed but not overwhelming. Together, it looks put together without looking like you tried too hard.

And at this point in life, that’s usually what I’m going for.

My Overall Thoughts on J.Jill Clothing for Mature Women

J.Jill does relaxed, wearable style very well. Their pieces are soft, breathable, and easy to live in. For women over 50, that matters.

Sizing runs generous in most tops. If you’re between sizes like I am, you may find yourself sizing down. For white pants, I sized up to a medium because I prefer a little extra room. White bottoms that are too tight are never flattering.

Not everything was a winner. Not everything came home with me. But several pieces absolutely made sense.

And that’s what I look for now. Clothes that make sense.

Now tell me. Are you team printed quilted jacket… or are you still undecided like I am?

Are You One Of The GURLS?

You’ll receive a daily email reminder from me, keeping you updated when a new blog post is published. Additionally, a special email might occasionally appear in your inbox, so be sure to keep an eye out for it.

To GOD Goes The Glory!

Verse Of The Day

Ecclesiastes 12:13 (NIV)
¹³ Now all has been heard;
    here is the conclusion of the matter:
Fear God and keep his commandments,
    for this is the duty of all mankind.