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Demystifying The “Boyfriend” Jean

A good pair of jeans is hard to find. Why? We women have a lot of variables in jean-covered body areas. Where it hits on your hip, how tight that cinch is, the angle from waist to seat, how tight or loose the legs are, these measurements create what my software friends mights call non-trivial permutations and combinations.

Then branding language steps in, adding smoke to the hall of mirrors.

Right now, in retirement, I’m searching for loose pants that are presentable in public. Fortunately, boyfriend jeans are in style. Unfortunately, there are 60 different varieties, and no consensus on just what “boyfriend” means. Loose? Ripped at the knee? What?

So I decided to order 4 pairs of ostensible “boyfriends,” so to speak, from various brands, to figure out just what makes for a good fit.

To demystify “fit” itself, I actually measured the pants when they arrived. I hate measuring even more than I hate tight pants, but I we’re a team, right? I measured the waistline (which never hits anyone’s actual waist these days), rise, (i.e. from crotch four corner seam to waistline,) high leg, (i.e. across the leg 3 inches down from crotch four corner seam,) and cuff,) i.e. across the leg at the bottom of the pants).

I chose these measurements, vs waist, leg opening, and inseam, as the online retailers might provide. Who the heck knows what a “leg opening” is? And if we’re rolling the jeans, we don’t care much about inseam, either.

For consistency, I’ve taken all these photos wearing the same J. Crew t-shirt, purple Nike Air Maxes, and UNIQLO footsies. Also a Rolex Cellini, and chandelier earrings from Beladora, because that’s how I’d likely leave the house. I’d also leave the house in a jacket, but I’ve left that out of the photos to show full details of the jeans.

Sneak peak at the final episode – they all looked OK, but some felt markedly better than others. Felt better both physically and psycho-socially, or whatever term we want to use meaning I Like The Woman Who Wears Them.

I sure hope someone besides me is thinking boyfriend. Otherwise these are a LOT of photos of denim on a middle-aged woman.

1. GAP 1969 Sexy Boyfriend Jeans – Koko Wash, Size 26 | $49.00 + $7.00 shipping

Waistband – 35 1/2″
Rise – 9 1/2″
Upper Leg – 10″
Cuff – 7″
Fabric  – 100 % cotton, dark, whiskered (those lines that look like bleached creases)

Front view,


and back.


These looked pretty good, but I’ve realized I’m not a fan of whiskering. And they are, believe it or not, too close-fitting. I told you I don’t like tight pants, right? But if you tolerate constraint, these are a fantastic deal.

2. Citizens of Humanity Skyler Loose Cropped Boyfriend Jeans via Piperlime | $229 + free shipping

Waistband – 34 1/2″
Rise – 9″
Upper Leg – 11″
Cuff – 6 1/2″
Fabric – 100% cotton, faded, a little frayed in spots

Front view,


and back.


I love these. The denim is so soft it feels like pyjamas. What? The rise and waistline are perfect for my dimensions. And the legs are just wide enough to make clear that this is a fashion choice and I’m not wearing my son’s pants. Which I’ve been known to do. The slight fold you see on the right in the back view photo is a crease from shipping, and will shake out. Also, note to the long-waisted, we might do best with a narrow cuff.

3. Current/Elliot 1957 Boyfriend – Loved Style via Barneys | $206 + free shipping

Waistband – 36 1/2″
Rise – 9″
Upper Leg – 10″
Cuff – 7″
Fabric – 98% cotton, 2% spandex, faded

Front view,


And back.


These I didn’t like at all. I am now clear that I do not like even a hint of flare at the cuff. And that loose pants don’t need elastane, or stretch of any sort. You heard it here.

3a. Random Backyard Plant, Because There Are Only So Many Pictures Of Myself In A Row I Can Tolerate


I forget what it’s called. However, it’s clearly very happy where planted.

4. Rag & Bone Boyfriend Jeans, Color Papillon, via Forward by Elyse Walker | $197 (now $146 but out of stock for the moment) + free shipping

Waistband – 36 1/2″
Rise – 8″
Upper Leg – 10″
Cuff – 6 1/2
Fabric – 100% cotton, very dark and heavy

Front view,


and back.


These I also liked. The fit is similar to the Citizens, but the denim is much heavier. But in the end, the pants pulled at my knees when I moved around with any enthusiasm.

So I’m keeping the Citizens, returning the rest. (Which means at least one pair of the Rag & Bones will shortly be available.)

I’m going to say that boyfriend jeans ought to mean a nicely fitted hip and waist, a wide upper leg, and a narrowed but not tight cuff. Good for rolling. I am also going to say that the amount of fabric jiggery-pokery isn’t key. Not everybody’s boyfriend has holes in their pants. I suspect the industry will pay me no never mind.

Key fit and comfort determinants turned out to be those measurements I’ve included, and the fabric. Duh, I suppose, but branding has a way of blinding one.

Which brings me to one final research result. Learn a lesson from your first love. I still remember my favorite pants ever, back in the 80s, when “paperbag” pants were the thing. Anyone remember? They were high-waisted (I’d bet the rise was more like 11-10″) and then very baggy at the high leg. I think I’ve been looking for them ever since.


For context, since I am trying to provide you a systematic review, I weigh 125 pounds, and am 5’5″. I used to rightfully claim another 3/4 inches of height, but such are our 50s. Note: This post may contain affiliate links which generate commissions.

67 Responses

  1. I really enjoyed this! Thanks for all your intrepid research.

    This style looks adorable on you. I find this style makes me feel playful and comfy, but also a bit like I’m dressing up as a 10-year-old boy. Which… hmm. Not usually my goal.

  2. Wow, you look great in them I have tried umpteen on but look awful in them, I have quite a curvy figure ( 37/27/36) but with very with skinny legs I need skinnies or flares.

  3. The denim on the Citizens looks fab. I struggle to find a pair of boyfriend jeans that fit me. The Gap version is way too short, others look a bit too 80s. I’m currently making-do with an old pair of loose-fitting J Brands, without a belt. Not so easy for walking around in though!

  4. I dropped what I was doing to read this. Thank you for the research. I find the GAP jeans to be pretty godd so glad you feel the same. Good to know about Citizens of Humanity. Appreciate the reserach. For something that is supposed to look so easy and casual, why is this so hard?

  5. Thank you, Lisa – the whole “boyfriend” thing has been confusing me for quite some time.

    I also agree that loose-fitting pants should not be made of any elasticized or stretchy material. Unfortunately for me, most plus-size pants are made of stretchy/elasticized material and are pretty baggy, especially in the legs, since I have an actual shape and am not 6 feet tall (I have to have almost all my pants at least shortened, if not outright tailored to fit my short, curvy frame, which explains why I live in inexpensive, off-the-rack capris all summer long). Every time I purchase a pair that fit really well in the store, they become loose and baggy a couple of hours after being worn. And drive me crazy – I’m constantly pulling them up.

    That being said, there are times I like baggy britches, such as this morning when I put on my “good” pair of black, winter-weight slacks and realized that if I walked more than 10 feet in them, they were going to fall down around my ankles. So I’m wearing a pair of faded, but comfortable, black denim jeans that I haven’t been able to fit into for 2 years. Yay, me.

  6. You are so systematic! Impressive. I recently passed my Current/Elliot boyfriends (more distressed than the ones you model above) to one of my daughter’s who was pleased. They just looked too sloppy on me. What I’m liking right now is a pair that fit fairly snugly before my weight loss and are just perfect as boyfriends now, although I need to remember a belt if I don’t want to accidentally walk right out of them (and I don’t!). They atarted as dark raw denim, so the only whiskering and fading is what I put there, and I find I like that look the best — closest to your Rag and Bones, which I really like on you. Too bad about the heavy denim, but great that you found a jean that feels comfortable and looks good. And it only took four pair to get there. And a lot of measuring!

  7. I love the Gap 1969s and they were my favorites on you. I’ve had mine for a few years, but mine are boot cut. They’re also size long, because I just can’t do ankle-cut jeans.

  8. why am i not surprised in the least that you liked the citizens the best? they are my favorite boyfriend jean maker + i’m eyeing a couple of pairs from the spring collection that i NEED. comfortable but polished. my mantra in jeans.

  9. Thank you – it’s great to see what specific jeans look like from the back, on a real person instead of a 20 year old model. Oh and did I say thank you . . .

  10. I think the one you liked best definitely looks the best on you. To find a great pair of jeans you love is kind of like the Holy Grail of clothes. And yes, yes, yes! to remembering that one pair you loved. I had two – the Guess jeans with the zippers at the ankles, and the Pepe jeans with the pink knees. I was definitely a child of the 80’s!

  11. I like the Gap and the dark wash on you best. Too bad there was not enough comfort when you put them on. Comfort and fit trump everything else.
    I think that plant might be a New Zealand flax.
    I am putting the finishing touches on a jean post as I find I am wearing mine 5 days out of 7. Gotta love dressing for retirement!

  12. I don’t do boyfriend jeans somehow they just seem to look silly on me. I prefer a classic straight cut but they must sit on the waist to avoid that terrible role of flesh at the top.

  13. The plant is definitely a New Zealand flax (Phormium ‘Duet’ is my guess.)

    Love the Gap jeans, but I’m kind of dumbfounded by the difference between the size (26) and the waist measurement (35??).

    1. @lizzo, Phomium! That’s right. And I have no idea what that 26 is supposed to represent. Are they inferring what my true waist measurement is? If so, they’re wrong…

  14. I JUST got the Gap one’s. I wasn’t sure. I thought maybe BF jeans were silly on me. And then I see this post and I say to myself ‘if Lisa can do it then I can.’ Thanks for the validation.

  15. I like the Gap on you the best as I like where the pockets sit on your rear, as opposed to the lower pocket on the C of H’s which look a bit saggy. But I do love the denim on those, so perhaps doesn’t matter? I need to do this same experiment – just order a bunch of pairs and try them and get a photo from the back as well.

  16. Am I the only woman on the planet who thinks $229 for a pair of jeans is very expensive? I buy brands (Talbot’s, Not Your Daughter’s Jeans, Lee, Levis) that top out at $120. It’s not that I can’t spend more- on me, I cannot see a definite advantage to the higher end designer brands.

    1. @Duchesse, Oh my goodness, yes! I am a value shopper and no jeans on earth would justify that price tag- even on a price per wearing basis. Plus I have never, ever, looked at someone and thought “where did she get those jeans, I want some like those!” And, too, I think that wearing anything pre-ripped is extremely disrespectful of those who are legitimately poor. That being said, the jeans fit nicely, Lisa, and it is your money to spend. I am respectful of that, as well.

    2. @Duchesse,
      That’s what I was thinking! I just bought some Levi’s at Kohl’s for $40, and thought they were priced just about right. The first pair I ever bought, 501s, were $9.

    3. @Duchesse, There are a few reasons. a) I don’t own any pants other than jeans. b) With these, I now own all of 2 pair that I will wear out of the house c) Jeans are to Californians as snow has always been reputed to be for the Inuit.

      Value is not absolute, it’s derived.

    4. @Duchesse, I was also taken aback by jeans at that price, but I’m a never-pay-retail girl. And with my current budget, even at 50% off, those would be too expensive for me.

      At the same time, I hope that you have lots of wonderful adventures in them, Lisa.

  17. My ankles aren’t so attractive that I want to put them on display by rolling up my pant legs. But the style looks great on you.

  18. You have a really slim stomach /waist area…Im really envious.

    Im wearing some sort of denim type pants at the moment ..dont know what they are brand wise but nothing like the Levis I used to wear

    1. @smr, I don’t, really. I have the same roll as most midlifers. But boyfriend jeans are much more forgiving then other pants. So they are working in these photos!

  19. to complicate matters…
    pret a porter featured “the girlfriend jean”
    say it isn’t so…
    now that is mystifying!

  20. Terrific post! I actually like the Gap ones best (there’s something about the pocket position that does it for me), though the Citizens are also great. You should make this a regular series!

  21. Great info, thank you! I’ve been living in my Eddie Bauer boyfriends. They come in several washes/lengths/styles, even button fly. Soft yet substantial fabric. They have 2% elastane(?) tho. If I wanted to graduate to 100% cotton would I size down or up? If I paid over a $100 for jeans they would not be for home lounging. I would probably wear 5 or 6 hours a weak and would prefer not to wash very often unless needed of course. How much do the cotton ones stretch?

    1. I believe the sizing is actually consistent within brands. I could have gotten a 25 in CoH, and I think they’d have fit. I am not yet sure how much the 100% cotton ones stretch between washings – maybe 1/2 inch? That’s just what it feels like, I have not measured.

  22. Honestly? Objectively speaking the Gaps look the best. The Citizens look the most comfortable.

    Thanks for this post. I was wondering what all the “BF jeans” hoopla was about. I may just buy some men’s jeans in the end – the softest, thinnest, cheapest ones I can find. The mens’ shape actually fits my body better.

  23. I love the idea of boyfriend jeans for their comfort, but I could never pull them off. What’s more, ever since I’ve discovered Eddie Bauer’s Curvy Fit jeans a few years ago, I haven’t looked anywhere else.

  24. I like the pocket placement of the Gap pants. I see that Lisa doesn’t have a belt on. Does the selected pair fit so well that they don’t droop as the day goes on? I must wear a belt with my BF’s and eventually found a web belt -will that be Google’s next frontier? The fastener is quite flat so it doesn’t produce lump and bumps in my torso.

    1. @Roseau, I don’t really like belts. I’m long-waisted, and I feel like they emphasize that more than is optimal. But a fabric belt is something I’ve thought about for a while…

  25. Those GAP boyfriends are my favorite look on you; I liked them so much I just went out and bagged a pair. Thanks for solving my boyfriend dilemma (just don’t tell my husband)!

  26. PS–I just saw your reply to Roseau: I dislike belts as well. I’m short-waisted with a barrel-esque ribcage, and can’t wear shirts tucked in. When I wear them out, the belt-buckle bulge just looks lumpy and weird. When a belt is absolutely necessary (I suffer from the gap-waist issue, and tailoring doesn’t always resolve it, as it can depend on the lycra content of the pants) I came up with the idea of using a boot-length shoelace in lieu of, tucking the ends into the waistband.

  27. Lisa,

    Have you tried Levi jeans? They have many different types of jeans and fits than when we were young.

    I find they look great and give me less of a flat rear-end.

    You know what we might enjoy….. posts about your meals and exercises.


  28. I started reading your comparisons and thought how much easier it would be to compare the pants if you put the information in a spreadsheet. I guess that says something about how I look at the world. Having bought tighter jeans only last year I’m not sure I’m ready for a new style, but I guess I should give it a try.

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