The Trajectory of You as Told by Your Jeans

A personal journey of denim proportions


Are we what we wear? Nah. Not in the present tense, at least. They might reflect who we want to be, tell the stories we’re not quite willing to, but at the bottom line, we are who we are. Point blank. Jeans are a different animal, though, they tell a great deal about who we were. Consider them a series of bench marks, a marker similar to the photo album perched between War and Peace and Sheryl Sandberg’s Lean In on your book shelf that possibly retains the memories you didn’t care to remember yourself. Sometimes they’re funny, sometimes they’re tragic, often they don’t make it past the five year mark but fundamentally and definitively they are always an iteration of you. So what does that say, right?

Boot Cut

Picture, for a moment, your year-2000-self. You danced to “Toxic.” You watched The O.C. You were 99% angel and layered your polos. You lived for the sound of your crush signing online. Your jeans, meanwhile, hung aggressively low, but so long as you weren’t getting detention, you didn’t care. The part below your knee flared out just enough so that it could hang down over your Rainbows and onto the ground, and you naively assumed this style would never fade out…


“There’s no way,” you said to yourself. “No way I’m trying jeans that suction-cup to my ankles. My legs will look fat, guaranteed.” For years your calves had room to breathe, until suddenly, the trend bended skinny.

But then the skinny jeans grew on you. You bought a pair from Old Navy as your starter pack. They looked “cute” with sweatshirts, and flats, and party tops, and flip flops. They made you look a little more polished. From there the addiction grew — All pants must appear painted! — and before you knew it you relied on old faithful like a crutch.

The Editor

College skinny jean transitioned into post-graduate cool with a color change (black) and fabric (waxed), and for the Francophiles, a lower waistband. Emmanuelle Alt was the immediate inspiration. You wore them to creative job interviews, dates and to “go out.”

These jeans lived, however, during the birth of the “boyfriend,” and for the first time in a long time two denim silhouettes shared your closet’s spotlight. Both styles were leg tested, editor approved and looked good with your one-paycheck-per-foot pumps.


Those boyfriend jeans were like a gateway drug. You started craving nonconformity and refused to be boxed in. No longer were jeans about looking sexy for you. Instead, they became a game of sartorial birth control. Why cover up one private part when — with the clasp of a shoulder strap — you could cover them all? Perhaps you also read a certain book.

Cut Offs

…But everyone knows that if you give a mouse a pair of overalls, she’s going to want to go to Glastonbury, which will remind her of that one time at Coachella. It was there in the California desert that you had your epiphany: nothing says music festival and youth like high waisted cut offs with fringe at the thighs.

You later learned that cut offs more-than-proved their worth in urban areas, too, where transportation does not include shoulder riding. Instead of a crop top, you wore a striped shirt, and instead of combat boots: a pair of flats. Your Alexa Chung phase commenced, and it’s possible you never looked back.

Super High

…Though chances are, you gave in to normcore. The shorts above were just the beginning of your ’80s resurgence: super high waisted mom jeans proudly declared that you gave zero fucks about your ass, and also, perhaps, that you were a victim of childhood wedgies. But they also opened you into a world of Saint Laurent’s practically-sprayed-on take of the the aforementioned college skinny.

Lady Cropped

If you remained a skinny jean loyalist but considered yourself a Charlotte (as opposed to a Carrie), the cropped ankle look provided that ladylike Audrey Hepburn effect.


And then, the 90s-redux set in. Your jeans looked incomplete without a little bit of grunge. You retained that post-Abercrombie complex bestowed upon you via your parents (“You could buy the same pair of jeans for 20 bucks, you know. Try doing a little yard work — it’ll rip your jeans for free.”) and yet you boldly maintained that you were in your artist phase. For about three months, you wore a plaid shirt around your waist like it was a fanny pack and you? A Disneyland dad.


…But then it hit: the 70s. As a short girl eternally in search of a longer leg, you got down on your knees and thanked the platform gods. (Then you re-watched That 70s Show and secretly compared your butt to Kelso’s.)

The Cropped High Waist Flare Leg Combo Platter

Or, for those born tall/anyone in-the-know at all, denim’s pièce de résistance currently resides in the form of a sartorial portmanteau (shout out to the style of Marcia Brady) whereupon the jeans are not only flared, but also cropped. The waist, high. The morale, higher; and you at your current stage-of-life, debating whether or not you’ll try out that whole Brooke Shields thing come spring while you silently pray the boot cut of year 2000 — still hanging between Lady Cropped and The Editor — has a fashion-adapted comeback. If only for the thrill of the memory.

Find out what more of your stuff says about you here.

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  • Megan

    Spot on. I just bought my first pair of high waisted flares in over a decade! 70’s for the win. If you go a little further back for those of us in their 30’s there was the ‘rave/skater’ look with massive elephant pants the likes if JNCO- don’t know if that’s coming back….

  • I’m glad the acid-washed and/or tie dyed jeans were tastefully sidestepped in this article. Those were really the WORST! I blame Guess jeans for those.

  • parkzark


    • Amelia Diamond


    • Martine

      You are so right!

  • AlexaJuno

    I embraced “Brooke” this morning and my ankles are nice and toasty. Good call, MR.

  • Catherine Bohner

    At 28, I still wear boot cut jeans that I buy at a store for preteens (Delias) interspersed with the occasional “whatever fits” from the thrift store. The flare also enjoyed a moment in 90s with the elephant pants, so if I’m lucky the boot cut will be back next.

    • Amelia Diamond

      Wait didn’t Delias close?!?! MAN THAT STORE RUELD

      • AlexaJuno

        I know for a fact that there is one in the Staten Island Mall. Anyone shocked? I’m not.

        • Catherine Bohner

          Its been a few years since I bought a pair but I think they’re still around. Their HQ is Lancaster (Amishtown), PA, so…anything goes?

          • AlexaJuno

            I’m pretty sure they’re still in business. I’m from Staten Island (but associate as little as possible) and that store is still up and running. Also, it should be said that your comment inspired me to dig out my old Delia’s flares and work them into my outfit today. So, cheers to us and Delia’s (who actually make some pretty good denim)!

          • Sa

            Sadly, the one in the SI Mall is out-o-bizz. RIP screen tees.

    • Martine

      Bootcut yes, low- rise bootcut; NEVER. I have some great Levi higher rise bootcuts with the 90’s fold over pockets. I love them, but the rise is ten inches or so, between hi and mid rise. I think they look great. Not going to wear cheap crap that is sewn together crooked like Delia’s or Fortever 21 or anything like that however. I never liked doing that.

  • Teresa

    I actually just purchased a pair of overalls off of ebay this past week, and they were delivered to my doorstep just yesterday. They are Keys Imperial in a slate herringbone pattern, the dapperest things I have ever put on my body, and I’m in love with them. The label on the front reads, “Key Imperial–Aristocrat of Overalls”. If that doesn’t say something about the quality of this purchase, I don’t know what does.

  • SUE

    I love the “If you give a mouse a cookie” reference. My fave book growing up.

  • ThisPersonSleeps

    Can someone recommend an affordable option for the cropped flare? I’m short so it would need to be very cropped.

  • Sartorial Birth Control. God bless.

  • theperriertree

    Help! Best cropped/high waist/flare combo pair for my 5’3 self?

  • hahaha post abercrombie complex. nailed it. totally me. i somehow can’t manage to wear a pair without rips now.

  • pm.

    Ugh, I hate being so understood! #croppedhighwaistflares

  • Sally Waits

    Great, now you made me buy that pair of vintage flares that I have been drooling over but kept myself from buying because the legs are actually too short. I’ll call it cropped now and be happy.

  • Lorrainemcdonnell

    There’s this thing called the Jeanjet that dries ripped jeans without damaging them.

  • crazyloverblue

    I want the editor pants! Both kinds!

  • Avocadoseeds

    I am totally the skinny jean

  • Naura

    Pardon me, but you overlooked a key category: The Cropped Dual Tone Flare Leg Strategic Cut-Out Nautical Overall “All-You-Can-Wear” Sampler (photo credit net-a-porter):

  • Bubbles

    Call me old fashioned, but my favorite pair of jeans are the ones lying at the base of the bed.

  • Lua Jane

    I’m true to the skinny jean since it came into fashion, and frankly I’d be very sad to see it go. Skinny fits my body shape, and boot cut that I wore before, just like pretty much everyone in early 2000, are horrible on me. I once bought Levi’s with insanely high waist and extremely wide legs, that could be worn with insanely high heels, but I gave them away because, as sartorially brilliant and men repelling as they may be, they were impossible to move in and therefore totally impractical. I also got two pair of boyfriend jeans that I wore maybe once or twice.
    I did however learn from mistakes, so latelly I stick to what looks best, and in my case it’s TOPSHOP Carey Moto jean. It has, although high waisted, that french, editorial dash to it and I feel like a member of Mademoiselle Alt’s pose wearing it.

  • Ola

    I tried mom’s jeans and I’m not sure about the outcome, check it out !!!!

  • Sophie

    I related, up to the Editor. After that I switched to leggings or maxi skirts, and am never going back. Sorry, denim. We’ve had a good run, but it’s over. I will never forget you but we just aren’t a good fit anymore.

    I still have one pair of stretch skinnies in my closet for those tops that only really go with jeans.

  • Flares all the way man…. and how did you know i’m a sucker for platforms? 😉


  • Grace

    In the 90’s I had an amazingly high waisted pair of long boot cut wranglers that had no stretch. That was the bar I set for all denim since.

    • Martine

      OMG, that sounds divine. Where are they now?????

  • In this list of style I have worn, skinny, overall and black boyfriend jeans.

  • Martine

    A 90’s era high waisted bootcuts would be a very welcome addition to my closet. Haven’t seen any yet. And I alsread have flared crops. I like them, but I need jeans that work for winter. In fact there is NO WAY the high rise skinny is ever going to completely phase out, because they are perfect with winter boots, and many of us DO NOT live in California or Florida. It gets very cold where I live.

  • Martine

    I wouldn’t wear alow rise pair of jeans if the fate of the world depended on it, Threw them all out about six years ago, and will never looik back. They were stupid and ugly when I first wore them