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R29’s Shopping Team Tries On The Everlane ’90s Cheeky Jean

Our love for the classic look of vintage jeans is often thwarted by how difficult it can be to actually find a good pair. From dealing with decades-old sizing to extreme wear-and-tear or potentially steep price tags, the whole retro-denim hunt is an ordeal — one that’s even further complicated when you’re attempting to conduct it virtually. So when we caught wind of a certain Everlane pair with best-selling vintage appeal, we knew it warranted a more in-depth investigation. The ’90s Cheeky Jean and The Curvy ’90s Cheeky Jean (cut for a more hourglass shape) are straight-leg pants (fitted through the waist, hip, and thigh, but relaxed from the knee down) ethically made from Japanese non-stretch denim with a mid-to-high rise, a button fly, a fit that’s supposed to give the booty a boost, and a palatable price tag of $88. While the regular ’90s Cheeky is offered in seven denim washes (aka every shade of blue imaginable), the Curvy ’90s Cheeky comes in black and two blues. For both styles, there are options for a “Regular” inseam of 28.5″ or an “Ankle” inseam of 26.6″.

The jeans boast reviews numbering in the thousands with an average rating of 4.4-out-of-5-stars and a general customer consensus that they are the “Perfect Everyday Jean,” equal parts comfortable and stylish. To answer the question of how these internet-favorite throwback jeans actually stack up IRL, several members of the R29 Shopping team were graciously gifted a free pair from Everlane to try on and suss out. Keep scrolling for a closer look at the real-life fit and feel of The ’90s Cheeky Jean.

Everlane The ’90s Cheeky Jean, $88

Available in white, black, and varying shades of blue, these jeans come in sizes 23 through 33 and are offered in Ankle or Regular lengths.

Everlane The Curvy ’90s Cheeky Jean, $88

Designed for folks with hourglass shapes, these Curvy jeans are made to accommodate and accentuate the hips (which can often be difficult to find in vintage denim). The 23-to-33 sizing is similar to the style above — but the washes are limited to three colors in Curvy.

The Curvy ’90s Cheeky Jean in Medium Blue, Regular Length

Tester: Mercedes Viera, Associate Deals Writer

What I Look For In Jeans: “The first things on my list when looking for jeans is comfort and fit. I have to be able to breathe and walk around in them without feeling like I’m dying. Obviously, I also like having variety in my jeans (aka different washes and cuts).”

First Impressions: “My first thought was how soft the denim was. I was worried that the fabric would be too thick for the hot day I decided to wear it out for the first time, but it was ended up being absolutely perfect — not too thick but not thin either, just good quality. I was also worried about the button fly because those styles of jeans usually don’t fit me very well. I was pleasantly surprised to find that not only did it fit but it also felt comfortable. Well, almost. I can sit comfortably but they are a tiny bit restrictive — but, as with most denim, I’m assuming the more I wear them the better they’ll form to my body.”

The Price: “My price range for denim is between $50-$70 so this $88 price point is a little more than what I usually spend, but the quality is more than worth it.”

The “Cheeky” Factor: “I didn’t notice anything personally — I think that side was a bit loose on me just because of my body type.”

How I’d Style These Jeans: “I’d style them with a turtleneck, sneakers, and a coat. Or, with a loose-fitting sweater tucked in along with boots and a coat.”

The ’90s Cheeky Jean in Vintage Sunbleached Blue, Ankle Length

Tester: Karina Hoshikawa, Beauty & Wellness Market Writer

What I Look For In Jeans: “Since I’m petite, I always look for a cropped or ankle length. Anything standard will likely be too long of an inseam for me. I pretty much exclusively shop for high-rise styles since I find them more flattering. I’m not terribly picky when it comes to stretch, but I obviously want them to be comfortable! I also want my jeans to last me a long time, so I don’t buy anything that feels too thin and jegging-like.”

First Impressions: “My first impression is that the fit was not bad, definitely true to size! I tend to struggle with finding jeans that don’t bunch up at the ankles since I’m 5’2. The denim feels moderately rigid, but not too much so that I can’t sit down comfortably. Plus, I’m sure they’ll soften up a bit over time. I got the Ankle length and, TBH, they were still longer than I expected! These ended up hitting me right at my feet; ideally, I’d love them just a hair shorter but I’m not mad about it. I love the high rise, too, and the pale blue wash was perfect.”

The Price: “Although I’ve splurged on some designer jeans from Rag & Bone and Frame that I am fully obsessed with, my general denim sweet spot is around $100. I own several pairs of Madewell jeans that I love and a few from Everlane, as well, actually! For the quality and transparency behind the manufacturing, I think $88 is a pretty fair price for people like me who are used to buying more premium (i.e. not fast-fashion) denim.”

The “Cheeky” Factor: “Maybe it’s just me, but I don’t feel like these did a ton for the tush. It didn’t not make my butt look cute but, then again, there was also some looser fabric around the thigh area that probably camouflaged my booty a bit. I cared more that the fit was snug in the waist area so you could still see some cake.”

How I’d Style These Jeans: “My style is pretty basic, so pairing these with a plain white tee OR graphic tee (I have faves from In-N-Out and Tabasco) layered under a leather jacket would be perfect for fall!”

The ’90s Cheeky Jean in Bone, Regular Length

Tester: Elizabeth Buxton, Deputy Director

What I Look For In Jeans: “The most important quality in a pair of denim for me is the fit — even if the things are rough and restrictive or stretchy and flimsy, I’d at least like them to provide a good-looking silhouette. I want a pair of jeans that doesn’t bunch up around my crotch or inner-thigh areas and instead creates long lean lines with some bonus high-rise hip-hugging appeal (is this too much to ask?!). I also care about length: anything two short and I look like I’m wearing a pair of capris; anything too long and it’s an early 2000s nightmare.”

First Impressions: “I’m not sure if it differs depending upon the wash, but the Bone colorway I opted for felt thinner and softer to the touch than I anticipated it would. Sometimes denim (I’m thinking of a few pairs of Levis I own) can feel dense and restricting before they’re sufficiently broken in. This pair was much more malleable and breathable on my lower half once I shimmied them on; I was able to crouch down with reasonable ease and sitting didn’t prove to be a noticeable problem either. I was originally eyeing the cropped length but had to opt for the regular due to availability in my size (for reference: I’m a 26) and was pleasantly surprised to find it actually hit my ankles appropriately (I clock in at just 5’5′ and non-cropped pants can often be too long for my liking). As a hot-and-heavy fan of tapered/bootcut denim, I found the fit was as expected in that department. I will note that the size 26 was a bit looser on me than my usual pairs so, if you like a tighter fit, I’d recommend sizing down. With that said, I actually didn’t mind the looser fit here — it gave it a decidedly more vintage vibe.”

The Price: “I’m willing to spend a good chunk of change on a really nice pair of denim because it’s a wardrobe investment that really does last (I own pairs that are 7+ years old!). My usual range is somewhere in between the $100-$250 price point per pair, so $88 is definitely more of a bargain in my book.”

The “Cheeky” Factor: “Full disclosure: I tried hard to snap a pic that made my front look more elongated in this style (it’s all about the angles, people) — but, since I don’t have the longest legs, these jeans didn’t really do much for me in that department. (Side note: I think they’d be great on someone leggier than I). However, as far as butts go, The ’90s Cheeky Jean’s real magic was all in their titular cheekiness. The high-rise fit coupled with strategic tailoring I’d describe as tapered around the waist/legs and looser in the butt/crotch worked wonders to provide me with a decidedly ‘90s-style booty pop. (For some reason I got Shania Twain vibes — but maybe I owe that to my snake-effect boots). I don’t know about a lift factor but I definitely can confirm that the derriere was this pair’s main event.” 

How I’d Style These Jeans: “Since these are a little looser on me than my usual go-to denim, I see myself staying away from chunkier sweaters/looser tops and opting instead for tighter tees/turtlenecks/sleeveless knits (like the one pictured above). In terms of footwear, I tried on a few pairs and found the bootcut best complimented (shocker) boots. I can also see myself easily throwing these on with a pair of clogs and thick-wool socks, too. For spring and summer, I really prefer a more cropped length and thus will be relegating these ’90s babies to a fall-and-winter rotation.”

The ’90s Cheeky Jean in Washed Black, Ankle Length

Tester: Jinnie Lee, Contributing Fashion Market Writer

What I Look For In Jeans: “I wear vintage Levi’s 90% of the time — 501s, 505s, 512s, 521s, 550s, and 551s. When it comes to leg shape, I generally like to wear straight, slightly flared, or slightly tapered. I also have a pair of super flared jeans and super wide-leg jeans. I never do skinny. I never do stretch, either.”

First Impressions: “With a name like The ’90s Cheeky Jean, I was hopeful these would fit similarly to my beloved vintage Levi’s. They don’t really (this Everlane denim is softer and looser compared to stiff ol’ Levi’s), but I actually think these are a solid alternative for regular jean-wearers who seek the ease of buying vintage-inspired jeans with modern-day sizing in mind. I will also say that I very much appreciate the Ankle length option — I’m 5’3” and it’s a revelation whenever I find a pair of jeans that don’t require further altering.”

The Price: “Any well-designed, ethically-made denim under $100 sounds like a good deal to me.”

The “Cheeky” Factor: “I thought these jeans were going to give me one of those up-the-crack wedgies, but honestly this pair just comfortably covered my cheeks. To that end, size down if you’re looking for that tighter-butt look!”

How I’d Style These Jeans: “Love it with a t-shirt, obvi. A big, creamy cable-knit sweater might be cute with Washed Black. I don’t really wear form-fit tops, but I think these jeans would look great with one of those body-hugging Y2K ribbed tanks that everyone’s wearing right now.”

The ’90s Cheeky Jean in Vintage Mid Blue, Regular Length

Tester: Alexandra Polk, Lifestyle Writer

What I Look For In Jeans: “When I buy jeans I look for at least a 28.5” inseam so they make it to my ankle (I’m 5’8” and have lanky long legs), a looser relaxed fit, dark wash, and thick hearty denim.”

First Impressions: “My first thoughts were, ‘Thank god I read the size chart’ because I’ve never owned Everlane pants before. As I was looking at the size chart I noticed the waist measurements seemed bigger than the size they aligned with. I’m usually a 27 but this time I got a 25 — so definitely size down. I could not achieve a squat in them when I first put them on. They are very stiff, which I actually love (especially over flimsy denim). Once I moved around in them, after an hour I could squat slowly. They are flattering on the waist and the tapered fit makes them easy to pair with anything. These pants are definitely a good fall wardrobe staple and could be styled all year round.”

The Price: “Unfortunately, the fashion industry caters to skinny, barely curvaceous bodies like mine, so it’s very easy to find jeans that I like and that make me feel comfortable for much less. Most of my denim comes from thrift stores, or I go for $50 pair on average. But I think that $88 is the perfect price for jeans if you’re back-to-school shopping and want one nice reliable pair or if you like to shop more sustainable, high-quality denim.”

The “Cheeky” Factor: “I have many talents, but that does not include having a full butt. I didn’t notice anything out of the ordinary with these jeans, but upon further inspection, I can tell they hit the waist at a flattering point which would help accentuate someone’s curves. My curves just happen to be a little shy.”

How I’d Style These Jeans: “I like how I styled them with this mid-length ribbed polo and a pair of platform sandals. When it gets colder out I’ll swap the sandal to a low-top white sneaker and pop on one of my cropped jackets from UNIF or Topshop. If the jeans were longer on me I would definitely throw on a heeled bootie and it would look fab. I also love how you don’t need a belt with these jeans — the waistline does all the cinching for you.”

The ’90s Cheeky Jean in Vintage Mid Blue, Ankle Length

Tester: Kate Spencer, Affiliate Strategist

What I Look For In Jeans: “DEFINITELY fit. I’m pretty petite, so finding a pair of jeans I don’t have to alter is like finding a needle in a haystack. I also prefer denim that doesn’t have much stretch and am a bit picky about the wash. I usually go for lighter, more vintage-looking shades.”

First Impressions: “I think the quality of this denim is great. This is a wash I wouldn’t normally go for, so it was nice to try something new. Since I’m familiar with Everlane sizing, I was prepared for this pair to fit a bit big on me…and indeed they do. Luckily, it doesn’t bother me too much since I like a looser straight fit, but they do ride lower and are not high-rise as pictured on the site.”

The Price: “I think $88 is a pretty good price point for a nice high-quality pair of jeans. I don’t personally buy new jeans very often, but when I do, I go for quality over quantity and usually score sale sections of my favorite high-end brands to find a pair that doesn’t cost an arm and a leg. The last time I bought a new pair of jeans was probably three years ago and I probably spent $150-$200.”

The “Cheeky” Factor: “Realistically, I don’t have much booty to work with so these jeans didn’t do much for me…I don’t think that’s the jeans’ fault though.”

How I’d Style These Jeans: “I think these are super classic so there are really endless possibilities with styling. Likely I’d wear them with loafers, a basic tank, and some sort of blazer or jacket situation over top.”

At Refinery29, we’re here to help you navigate this overwhelming world of stuff. All of our market picks are independently selected and curated by the editorial team. All product details reflect the price and availability at the time of publication. If you buy something we link to on our site, Refinery29 may earn commission.

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