I Finally Tried All The Gap Jeans I’ve Been So Curious About

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If there’s one item of clothing I seem to always be chasing after, it’s jeans.

I have an obsession with finding the Perfect Denim. I don’t mean “the one pair of jeans that can do it all” — because I’ve recently decided those don’t exist — but rather, denim that’s just so dang good, you want to wear them repeatedly.

Jeans so good, you dig them out of the laundry basket because you simply can’t wait to wash them.

A pair of jeans that make you feel so confident that you can slip on any ol’ shirt and shoes and feel like a fantastic outfit just unfolded around you.

The Perfect Denim can be more than one pair, but it’s often still very hard to find. It takes trying on many different styles, sizes, washes, compositions, inseams and rises to see what you love best. But I’m committed — I’m always committed to this task.

Searching For The Perfect Denim: A Gap Jeans Try-On (+ 2 Bonus Pants)

Lately, I’ve had my sights set on Gap.

I’ve been increasingly intrigued by its denim catalog, so I finally ordered a handful of styles to take for a spin myself, including the High-Rise And Sky-High Cheeky Straights, High-Rise Barrel, High-Rise Stride and High-Rise ’90s Loose Jeans.

If there’s 1 takeaway in this try-on, it’s that Gap makes some of the comfiest pants I've ever put on my body (both jeans & other styles).

If there’s one takeaway in this entire try-on, it’s that Gap makes some of the most comfortable pants I have ever put on my body (both denim and other styles). I was impressed more than I was let down, and I can safely say I found at least two pairs that could be strong contenders for the Perfect Denim.

For A Vintage Fit: Gap’s Cheeky Straight Jeans

The Cheeky Straight Jeans collection is the entire reason I began looking into Gap’s catalog of denim as a whole. Even as the trends are seeing jeans get lower and looser, I’m still such a sucker for a good, classic straight-leg. 

The Gap Cheeky Straight Jeans come in both High-Rise (11 inches) & Sky-High (12 inches) versions.

left: sweater | high-rise jeans | shoes
right: sweater | sky-high jeans | shoes

The Cheeky Straight comes in both High-Rise (11 inches) and Sky-High (12 inches) versions, so I needed to try them both.

1. High-Rise Cheeky Straight Jeans

As I’ve stalked the Cheeky Straight over the past year, I noticed that new washes sell out fast. It’s a testament to how popular this style is. 

Right away, the Gap Cheeky Straight jeans reminded me of Levi’s Wedgies. They're perfectly snug around the waist, hips & bum, which I love.

sweater | high-rise jeans | shoes

The good news? There are multiple washes to choose from, and Gap frequently restocks them as well as adds new ones.

Right away, the Cheeky Straight jeans reminded me of Levi’s Wedgie jeans. They’re perfectly snug around the waist, hips and bum, which I love. As someone without curves, I often have a problem with denim looking a bit too baggy around my hips and thighs, so the Cheeky Straight was an instant win in that department.

The Medium Destroy wash of the Gap High-Rise Cheeky Straight Jeans appears to be lighter in real life than the online images. The distressing, though, is comparable to that of designer jeans I own.

sweater | high-rise jeans | shoes

The Medium Destroy wash appears to be a bit lighter in real life than the online images, which I was somewhat bummed about.

The distressing, on the other hand, seems to be very well-done and comparable to that of designer jeans I own (distressing on denim is not created equal, in my opinion, so I can be pretty picky about it). 

2. Sky-High Cheeky Straight Jeans

For whatever reason, I had it in my head that I ordered one pair of Cheeky Straight jeans without any distressing. Alas, both pairs of denim are pretty similar in having destroyed elements. 

I like 100% cotton jeans, but surprisingly I prefer the Gap Cheeky Straight feel over Levi’s Wedgies, & can see myself replacing the stiff Wedgies in my closet with these jeans. 

sweater | sky-high jeans | shoes

I like the destroyed knees a little less on this pair, yet I enjoy the higher rise a lot more. 

Both jeans are the same composition and slightly stretchy, but they do have a great vintage-denim appeal. As someone who typically prefers 100% cotton jeans, I was surprised to find that I prefer the Cheeky Straight feel over Levi’s Wedgies, and can see myself replacing the stiff Wedgies in my closet with these jeans. 

The fit of the Gap Sky-High Cheeky Straight Jeans is spot-on, & I loved the length on my 5’9” frame.

sweater | jeans | shoes

Fit notes: I’m wearing what I typically consider my true size, a 28 long, in both pairs of the Cheeky Straights. The fit is spot-on, and I loved the length on my 5’9” frame.

Trending Styles: Gap’s Relaxed-Fit & Wide-Leg Jeans

Loose denim is continuing to rise in trends, and while a lot of brands have only dabbled in this style in recent years, I think long, relaxed jeans will truly dominate this fall/winter season.

Loose jeans are continuing to rise in trends, & I think long, relaxed jeans will truly dominate this fall/winter season.

jeans: left | middle | right
outfit details: sweater | shoes

Gap is a fantastic place to try out this style of jeans if you’re unsure about it for your own wardrobe. If you already know you love this fit — Gap is holding its own among the rest.

1. High-Rise ’90s Loose Jeans in Organic Cotton

Denim with a ’90s style is perhaps my favorite across all denim, in all brands. If I see this name in jeans, I’m immediately tempted to try it.

Gap’s High-Rise 90’s Loose Jeans are relaxed through the hips and legs, and the jeans have a long, straight fit with a 12-inch rise.

Gap's High-Rise 90's Loose Jeans are relaxed through the hips + legs, & the jeans have a long, straight fit with a 12-inch rise.

sweater | jeans | shoes

The ’90s Loose Jeans are made with 99% organic cotton and 1% elastane, which makes them considerably stretchier and more comfortable than I was expecting. Is this try-on making me actually enjoy elastane in my jeans again?!

Gap has a lighter-blue wash in the High-Rise ’90s Loose, and there is also a Mid-Rise ’90s Loose with a handful of options.

The Gap '90s Loose Jeans are made with 99% organic cotton & 1% elastane, which makes them stretchier & comfier than I expected.

sweater | jeans | shoes

Fit Notes: I ordered the same size (28) in all the jeans from Gap for this try-on, but the ’90s Loose pair definitely fits oversized in comparison. The ’90s Loose also have a slightly longer crotch, so for this reason I would be tempted to try one size down so the waist fits better and for the hopes of a slightly shorter drop of fabric between the legs.

I’m wearing a “long tall” inseam, and they’re plenty long — perfectly pooling around my shoes for what’s “in trend” right now, but they’re perhaps a bit too long when barefoot. 

2. High-Rise Stride Jeans

Gap’s High-Rise Stride Jeans were an instant obsession upon pulling them on my body. They’re actually very similar to the ’90s Loose jeans, with a few particular differences that made a big deal for me, though they might be hard to see in photos. 

The Gap High-Rise Stride Jeans have a chic, long, wide leg with a little stretch, & they fit perfectly in the booty.

sweater | jeans

The fit of Gap’s Stride jeans is relaxed and, ironically, quite a bit looser in the legs than the ’90s Loose style. The waist and hips, however, are actually fitted to the body (whereas the ’90s Loose were very baggy). The High-Rise Strides are also considerably longer in the leg and have a 1-inch shorter rise (11 inches), which eliminates any dropped-crotch situation (thank goodness).

Overall, I adore how the High-Rise Stride Jeans fit. They have a chic, long, wide leg with a little stretch, and they fit perfectly in the booty. This is a pair I’m eager to style up in different ways, plus I feel like these simple shots don’t quite do them justice.

On Gap's High-Rise Stride Jeans, the waist was a perfect comfort fit, not too tight but not loose enough to want a size down.

sweater | jeans

Fit Notes: I’m wearing a 28 long tall. The waist was a perfect comfort fit, not too tight but not loose enough to want a size down. The inseam is lightning long. I absolutely do not need a “long tall,” but I would highly recommend these for my sister who’s 6’1” if she wants true full-length jeans! I already ordered a 28 “long” for myself which will be 2 inches shorter.

3. High-Rise Barrel Jeans

I think of barrel jeans the same way I do UGG boots and Birkenstock clogs: lovable, even though they’re, uhm, considered kind of ugly. 

UGGs and clogs don’t get any accolades for their flattering shapes, but they’re comfortable and — magically — so cute with outfits.

The same can be said for barrel jeans.

Gap's High-Rise Barrel Jeans are 100% cotton. I love the detailing on the waistband, the distressing is well-done, & the comfort is 10/10.

sweater | jeans | shoes

I recently began collecting this style of denim from other brands because there’s something statement-making about the fit while being remarkably casual, “off-duty” jeans. Barrel jeans are so good in all their quirkiness. 

Gap’s High-Rise Barrel Jeans are 100% cotton and really well-made. I love the detailing on the waistband, the distressing is well-done, and the comfort is 10/10.

The extra fabric that hangs around my thighs wouldn’t normally be something I’m into, but I do think it adds to the funky character of the jeans. Plus, I really like the way they look from behind.

I’m wearing a 28 long tall, & they’re a perfect fit for what I like, albeit longer than how the model is wearing them.

sweater | jeans | shoes

If you need a pair of jeans to sit on the sidelines at a weekend tournament or ring your cowbell during your kid’s football game, these jeans. If you need something easy to slip into for errands, these jeans. But also? Pair with heels (if that’s your thing) and a tighter top, and you’ll be New York-ready for date night. 

Fit Notes: I’m wearing a 28 long tall, and they’re a perfect fit for what I like, albeit longer than how the model is wearing them. If you’re taller than me (5’9”), I’d still try this pair because you would get a similar look to the model!

A Little Something Extra: Faux-Leather Flares & GapFit Runaround Pants

I couldn’t help but throw a few extra, non-denim pairs of pants into my cart when I was shopping.

Gap has got it going on these days, & I would have regretted not trying faux-leather flares or the GapFit pants I've been eyeing for months.

left: sweatshirt | pants | shoes
right: sweatshirt | pants | shoes

Gap has got it going on these days, and I would have regretted not trying faux-leather flares or the GapFit pants I’ve been eyeing for months.

1. High-Rise Faux-Leather ’70s Flare

I had to try these pants. A ’70s flare is admittedly not my usual go-to, but I became such a big fan of faux-leather pants last year that I was instantly excited to see a new style emerge (other than the classic straight everyone seems to make).

The faux-leather of Gap's high-rise '70s Flare Pants is buttery soft, not paper thin, but not too thick that they're suffocating. The quality is simply impressive.

sweatshirt | pants | shoes

The first thing I noticed about the High-Rise Faux-Leather ’70s Flare Pants was how well-made they are.

The faux-leather is hands-down better than most others I have tried (and last year I tried on A LOT). The pants are buttery soft, not paper thin, but not so thick that you immediately picture Ross Gellar in a bathroom covered in baby powder. The quality is simply impressive.

What’s clear is that I do NOT need “long tall” in any of the pants from Gap…yet, I weirdly like them on me with this extreme length.

sweatshirt | pants | shoes

I imagined rocking these in a casual, almost-grunge way, but if you’re someone who likes to get dolled up, these would be remarkable with a statement heel.

I didn’t think I would actually keep these ’70s Flares, but I don’t know…something about how soft they are is making me think I should try to have some fun in them.

Fit Notes: I’m wearing a 28 long tall, and what’s clear is that I do NOT need “long tall” in pretty much any of the pants from Gap…yet, I weirdly like them on me with this extreme length. This is good news for anyone taller than me, Gap has long legs COVERED!

2. GapFit High-Rise Runaround Pants

GapFit’s Runaround Pants are an item of clothing I’ve been watching closely over the past month or so. I absolutely adored the entire outfit the model was rocking, but I wanted a logo sweatshirt to wear with them (just like the model) and waited until one was stocked that I really loved.

Once I found the Vintage Soft Hi-Low Hoodie available in a few logo prints, I added both the pants and sweatshirt to my cart!

Gap's High-Rise Runaround Pants are a lightweight & stretchy fabric that is stellar for hot &/or humid climates.

sweatshirt | pants | shoes

The High-Rise Runaround Pants fit like much softer track pants. They aren’t excessively swooshy when you walk, but are still a lightweight, stretchy fabric that can be thrown on for just about any activity or errand.

The pants are glorious for hot, humid weather. It was a sunny and 98% humidity day when I did this try-on, and pulling on GapFit’s Runaround Pants was an instant comfort (and sigh of relief). These pants would be stellar for anyone living in hot and/or humid climates.

I ordered a size down in the Gap High-Rise Runaround Pants, but I wish I'd ordered the longer inseam in my normal size.

sweatshirt | pants | shoes

Fit Notes: Based on reviews, I ordered a size down than my normal and went with a small (regular). I mostly like the fit; I think with a stretchy waistband you can get away with a few different sizes, but I found myself wishing I had ordered the longer inseam in my normal size. I’d be curious to try them in my true size, medium (tall)!


The verdict? Gap denim is truly impressive and a lot more comfortable and flattering than I was expecting.

While I went into this try-on predicting that the Cheeky Straight and ’90s Loose would be my favorites, it was actually the Barrel Jeans and High-Rise Stride that I loved the most. Both pairs deserve to be properly styled up with my entire wardrobe (and if you want to see that, let me know!).

Xx,
Amy

Let’s be friends on Instagram! Sharing life from my sleepy little beach town, daily style, makeup favorites, Gilmore Girl binge-athons and endless cups of coffee — all with a good dose of adorable toddler content too.

Oh hey Pinners…

The item of clothing I'm always chasing after? Jeans. The Perfect Denim can be hard to find, but Gap is acing it. From high-rise to wide-leg pants, I can't get enough.