I’m a personal stylist. Here are 7 things I’d absolutely buy at Gap right now — and 3 styles I’d skip.

• I’m a stylist who headed to Gap to see which of its fall wardrobe staples I’d buy right now or skip.
• I loved Gap’s Stride wide-leg jeans, twill barrel pants, and men’s 100% cotton crewnecks.
• However, I’d probably pass on the retailer’s belts and super-trendy Y2K styles.

As a personal stylist who happens to be an elder millennial, I’m nostalgic for all things Gap.

From around fifth grade through high school, everything I wore had a Gap label, down to my socks and underwear.

The American retailer, which has been around since the late ’60s, was the first stop on any Saturday at the mall and my go-to spot for jeans, ribbed half-sleeve turtlenecks, school-dance outfits, and Dream perfume.

Though I eventually began shopping there less, I’ve heard recent murmurs about the retailer getting “cool” again.

In 2024, fashion designer Zac Posen was named its creative director. Then, this year, Gap has dropped several well-received collaborations with trendy brands like BÉIS luggage and Dôen.

As a former “Gap Girl” looking for a fall wardrobe refresh, I wanted to see for myself if the brand was really on a winning streak.

I’m happy to report that after a morning of trying on clothes at my local store, I agree that a “Gapaissance” is happening. However, I’m not sold on all of the retailer’s offerings just yet.

Here are my top picks and skips right now.

Gap’s Stride wide-leg jeans really won me over

I’m admittedly a denim snob. I typically shop premium denim for myself and my clients and am always ready to give a myriad of reasons jeans are worth investing in.

Then, I tried on Gap’s $90 high-rise Stride wide-leg ankle jeans. Y’all, I loved these jeans. They felt high-quality and sturdy, and I immediately wanted to purchase them — perhaps in several different washes.

I’m 5’4″, so while I don’t seek out petite styles, the ankle length was perfect.

They have a little bit of stretch (they’re made with a bit of elastane), making them more comfortable than a ’90s-style 100% cotton jean.

With all Gap jeans, I highly recommend trying on your typical size, a size up, and another size up. They may all likely fit, but you can choose which you prefer to style and move around in.

I went up two sizes for an extra roomy fit. When the weather cools down, these will be perfect with a brown suede ankle boot.

Gap’s ultra-soft baggy jeans were a win — especially paired with a classic T-shirt

I don’t believe in wearing pajama pants in public. However, jeans that look amazing and feel like pajamas are totally acceptable.

Gap’s mid-rise UltraSoft baggy jeans are the perfect combination of cotton and TENCEL (known to be soft and durable), giving them a broken-in feel.

I’m a high-rise girl. Since these were a bit too mid-rise for my liking, I opted for a pair two sizes up from my usual size and cinched them with a belt for a drapier fit.

These pair well with a classic T-shirt, so I was glad to see that high-quality, simple white tees are still a Gap signature. At just $20 each, the price is right, too.

I preferred the thickness of the men’s 100% cotton styles, but I don’t think you can go wrong with the women’s versions.

And to complete this look, I’d add chunky jewelry or a boxy jacket.

The mid-rise twill barrel pants will be a fall staple for me

Gap’s mid-rise twill barrel pants are under $100, come in several autumnal shades, and feel high quality. I love how the side pockets are sewn in a way that creates no awkward gaping.

Honestly, I’ll be buying these instead of the similar pair on my wishlist that retails for about $400.

The barrel pants are such a blank canvas — for a cheery vibe, pair with a red sweater and loafers, or fully embrace fall trends with a leather jacket and ankle boots.

I wore these true to size, but for a slouchier look, you can always size up.

You can’t go wrong with a classic crewneck sweater

No matter your gender identity, do not sleep on Gap’s menswear.

These 100% cotton crewneck sweaters from Gap are perfect for Zoom calls and grocery-store runs. They’re under $50 and come in a range of colors, from neutral ivory and brown to a vibrant lily-green and deep red.

I prefer to wear these a little bit oversized and tucked in.

This chore jacket from Gap is an absolute score

Chore jackets and barn jackets are on trend this fall. If you want to give the boxy, sturdy styles a try, Gap’s UltraSoft denim swing chore jacket is a fantastic place to start.

The dark-blue indigo shade has a Japanese denim vibe, but the fabric feels soft and wearable. It looks way more expensive than its $148 price tag, and the corduroy collar is a nice touch.

It could be worth stocking up on the retailer’s heavyweight crop T-shirts

I also found myself impressed by Gap’s VintageSoft heavyweight crop T-shirts, which are under $40 a pop.

This is the kind of versatile top you wear once, then immediately want to buy 10 more of. It’s thick, soft, and made of 100% cotton.

In order not to show my belly, I went up a size. I also cuffed the sleeves to polish up my outfit.

I can see myself wearing this shirt all the time, with jeans and a mule or sneaker in the fall or with cutoffs in warmer weather. I could also imagine myself throwing this cropped shirt over my yoga clothes as an extra layer all year round.

On the other hand, I wasn’t impressed by some of Gap’s black pants

Gap has several fantastic workwear styles, but I was disappointed in some of the black crepe trousers and stretchy ponte pants I found.

They looked a little cheap to me, so I didn’t even bother trying them on. Maybe it was just the lighting in the store, but some pairs had a slight sheen that I don’t think would look very great in the fluorescent overheads of an office.

When I felt the polyester and nylon-blend fabrics, I could already picture someone’s sweaty-kneed future. They’re not nearly as breathable as cotton or linen.

If you’re buying black pants at Gap, I suggest looking at its denim or other twill options instead.

The belts didn’t impress me as much as I expected

I was excited to look through the belts at Gap, as I fondly remember purchasing one from the retailer in the early aughts that lasted me a good 10 years.

Though my store had several stylish belts — including ones made of 100% leather — I wasn’t super impressed once I picked them up.

Some of them felt a little flimsy or too thin to me. I’d rather purchase a belt with more heft to it, whether that means a style made of more supple leather or one with a heavier buckle.

Personally, I like to buy my belts secondhand. Ebay and Etsy have loads of durable options and vintage picks.

I’d skip the super-trendy tulle and lace garments — Gap’s real strength is its timeless cotton pieces

Y2k is trending, with baby tees, low-rise denim, and Christian Louboutins coming back for another stylish turn.

It was nice to see that Gap had several on-trend offerings, from tops with tulle and mesh details to slip dresses with lace trim. However, in my opinion, some of these pieces didn’t feel as nicely constructed as others I tried.

These uber-trendy pieces aren’t exactly timeless closet staples. It’s more likely they’ll last just a season before being discarded or once again going out of style.

For example, the sheer tulle embroidered top looks like something I would’ve bought in the early 2000s, worn once to the bar, and then never reached for again. Though I can also see how these styles could look great on teens, they also may read too young on adults.

All in all, this section felt like a far cry from the many fine denim, khaki, and cotton staples in the rest of the store — the things Gap clearly excels at.

Personally, I’d stick to the enduring classics at Gap and perhaps look elsewhere for more fun attire that may not be trendy for long.

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