Gap Fall 2025 Try-On: Great Real-Life Basics For Women Over 50
I hadn’t thought about Gap in years—until I walked in on a whim and remembered why I used to love it. I used to shop at Gap as if it were my part-time job. Back when our kids were little, I loved buying their clothes at Gap Kids too. I could get matching shirts for my son and husband, which I’m pretty sure neither of them thought was as much fun as I did.
Over the years, I started shopping at other places and, honestly, forgot all about Gap. But my curiosity got the better of me, and I wandered into a local store recently… and was pleasantly surprised. The jeans were still solid, the prices still reasonable, and—shock of all shocks—I found real-life basics I’d actually wear now. So this Gap Fall 2025 try-on wasn’t planned, but it turned out to be worth sharing.
In this post, I’m trying on several new fall arrivals from Gap, including updated denim, easy knitwear, and timeless outerwear. I’ll share sizing tips, fabric details, and ideas for how to style these pieces if you’re over 50 and want clothes that work in real life.
Spoiler: they’ve stepped up their game without losing that classic, clean Gap feel.
If you’re new here, welcome. A try-on is when I pop into a store and style pieces from the latest collection so you can see how they look on a real woman over 50. I share sizing tips, fit impressions, and ideas for how to wear them. For reference, I’m 5’4″, on the cusp of petite, with broad shoulders and straight hips. You can find my other try-ons here.
Gap is a size-inclusive brand carrying regular, petite, and tall sizes in XS-XXL.
Cashsoft Cardigan and Tailored Knit Trousers
I loved this outfit and would wear it on repeat all fall. The Cashsoft name is slightly misleading because this cardigan doesn’t contain cashmere…which is a plus for those who are sensitive to wool and cashmere. I’m wearing the gorgeous Wind shade, and it’s also available in other colors. They also offer a coordinating tank here, so you can wear it as a twin set.
These tailored pants are a heavier knit than the sweater. They have a zip and button closure, a structured waistband, on-seam pockets, and are as comfortable as sweats! These have a straight leg and are fitted through the hip and thigh…but not tight. I’m wearing black, and they also come in brown. The website does not appear to specify the inseam, but I’m wearing a regular, which is a smidge too long for me. These pants would be perfect for work or dinner out, and would be just as fabulous for an afternoon of snuggling on the couch with tea and a great book.
Column of Black With Classic Denim Jacket
This is a flat-out classic denim jacket, labeled Icon for a reason. It’s a medium indigo wash, made from non-stretch denim, with a point collar, button-front closure, chest flap pockets, and long button-cuff sleeves. It’s a straight, easy fit that hits at your hip, depending on the length you choose. The buttons are silver-toned, which I love.
I’m styling it over this organic cotton tank top, which is a nice heavyweight in a cropped length. It’s called ultra cropped, but on me, it hits at my waist in the regular length. This comes in several colors for layering. These pants are a pull-on style in thick ponte knit, which, to be honest, rival some I’ve tried on at 3 times the price! I could only find the large, which is a bit loose but totally wearable, so I would say they run small. These come in 5 colors and have a slimming seam down the front of each leg. These flares work great with sandals now and loafers or booties later this fall.
Classic Trench with White Shirt and Straight-Leg Jeans
This Icon trench coat comes in tan or black in regular, petite, and tall. This is a regular which is too long for me, so the petite would be better. It’s water repellent and fully lined with all the traditional details of a classic trench coat. I’m wearing it over this organic Oxford shirt, which is miles too large for me…because it’s selling out fast. I tied it at the waist to control some of the fabric, but this would be better worn untucked over narrow pants. It comes in 11 other colors and lots of stripes.
I’m wearing it over these straight-leg jeans in the medium wash. I clearly needed the petite in these because they’re several inches too long for a straight. This style comes in 34 washes, so it must be a customer favorite. It’s slim through the hip and thigh, but not skinny.
Chunky Cotton Sweater and ’70s Flare Jeans
I love a great flare jean, and this pair fits the bill. These high-rise ’70s flares have a very flattering fit with a nice amount of stretch. I could only find the regular length in the store so I am standing on my tippy toes because the inseam is 32″. The petite has a 30″ inseam, and talls have a 34.5″ inseam so they are intended to be worn with a bit of a heel. They’re slim through the hip and thighs then flare to a 21.5″ leg opening.
My color seems to be sold out in the oversized cotton sweater, but it comes in 5 other options. It’s a great cozy sweater for milder weather and/or those who dislike wool.
Cynched Denim Jacket and Dark Wash Jeans
This Cynched denim jacket was a delightful find! It has a flattering, feminine shape that elevates the look from the boxy ones. This is a low-stretch denim that curves in all the right places. I’m wearing the medium indigo, and it also comes in black or white denim. I wish I’d buttoned it to show you the full effect (my bad), but I seldom close my denim jackets, so I forgot.
These are the same ’90s straight jeans I showed above, this time in the dark rinsed wash. I paired it with this organic cotton tee in pretty pink. It also comes in 13 other colors, including a stripe. These tees are a great quality and you can’t beat the price!
This little trip down memory lane reminded me that some brands really can grow up with us. Gap may not be on every fashion insider’s radar, but if you’re after real-life basics that look pulled together without trying too hard, it’s worth a second look.
I’ll definitely be keeping an eye on their fall lineup. And if you’ve wandered into a Gap lately, I’d love to hear…were you surprised too?
Thank you Jennifer. I love the cynched denim jacket!! Last time I bought a denim jacket you shared it from Loft. I am always looking for a longer denim jacket. Love all your looks from Gap
Hi Jennifer, do you know anyone that has a THICK long sleeve white tee, preferably 100% cotton for the fall ? It seems no one makes good thick tees anymore. I do not like the paper thin tees. Thank you !
Try COS, they make terrific ones
I like the Gap. At one time they included the upper thigh measurement in their pants sizing information and I found that to be very helpful. Compared to Old Navy I find that their sizing is more consistent. A size 12 stays the same across different styles of pants. Sometimes with Old Navy a size 12 can change even within the same style item! I find that their clothes are well made and have details in them that cheaper brands leave out.
They’ve closed stores over the years, there is a store in an inconvenient place sort of near me. So many of the newer shopping areas have declared a war on cars and are built with not much parking that requires one to drive into a tower and pay.
I’m not a reactionary, but I wish the “cars are a thing of the past let’s design public spaces that don’t have easy parking” would lay off.
With that said, their returns are really easy, although the UPS store I take them too is also in one of those “let’s make it hard to get here in your car” areas. Baahumbug….
Fun post, Jennifer. I haven’t been to Gap in ages. Like you, when the kids were young I shopped there often. Then when the grands were little, I shopped there again. It’s time I stop in to see what they have for me.