Necessity is the mother of invention... or rather style in this case. While I definitely didn't invent the cropped jean, its permanent place in my wardrobe came from having no other choice... and maybe a little bit of thrift. Standing just over 5'2", I have been hacking off my jeans since college in the 80s, when I didn't want to waste any of my ski-lift-ticket money on a trip to the tailor.
And to this day, the wardrobe item I wear more than absolutely ANYTHING else is a pair of jeans that hits well above my ankle. I love a long-long-long flare on tall women, but for me, it just makes me look shorter. So I just leaned into it. I have no idea when I started to wear them REALLY short (maybe it was a mistake in a hurry with the scissors?) but I grew to really love the proportion on my short-legged frame, and the way the raw hem curled up into a fray after going through the wash. I'll have them hemmed when I want them a little more polished, but most of the time it's just a pair of craft scissors and a steady-ish hand. It works with flats, boots, heels... and it's especially good with ankle straps and "special" shoes that you want to show off a bit more. This is nothing new, and we have loads of styles available to get this look, no matter your height. Even if they don't come cropped, it's a pretty DIY (or tailor job if you prefer an original hem.) I get my own jeans hemmed a few inches, and for a little more of a kick flare, I love the J Brand Selena as a ready-made version... they're perfect length on me from the get-go. If you like patch pockets, the Lord Jim style from Seafarer has a chic nautical thing going on.
But aesthetics aside, the real reason I love these so much is that they conjure up one of my sweetest memories. Often your favorite things have something going on in your psyche as well as in your closet... and these are no exception. My oldest daughter was in middle school in the early 2000s, the era of tight, flared jeans that puddled at the bottom and completely hid your shoes... the longer the better. (My personal hell!) And because she grew UP before she grew OUT, the only jeans that would fit were fine in the waist, but hit way above her ankles. Just the way I like them, of course. (She still has very long legs... a gift of course but she hated it.) She was self-conscious and awkward and in hindsight I could have been more sensitive to that. But the stylist in me was just agog at how cool she looked! This was very much my look and I couldn't say it enough: "sweetheart, you look amazing, I promise." During some back-to-school shopping trip, I forced them on her with a flip "you're FINE... it's these or nothing" followed by a frustrated "oh, by the way, do you REMEMBER that I am actually not only your mother but a fashion editor???" Trying to convince a 13-year-old that you are both cool & smart is a lose-lose (though I kept trying) and she would trot off to school LOOKING fantastic but feeling terrible. Truth be told, the middle school audience probably didn't appreciate all the outfits we were concocting in her mint green bedroom (even if I did) but even after she grew into her legs, it was a great lesson. No matter what someone says to you about how you look, no matter how many compliments and "you look amazing"s you get, you KNOW how you feel and that trumps all else. How we feel in our clothes can't be separated from how we feel in GENERAL...
Which is actually why — fast forward to today — I end up in my cropped jeans so often. They are like the security blanket of my wardrobe. My team at work knows I am having a tough week when I show up 5 days in a row in my trusty J Brand Selenas and a menswear-style shirt or soft cashmere sweater. I may be feeling down or overwhelmed with the 60 million things I have going on, and I just don't have the energy to think of something fantastic to put on... I go for what I know and love and can move freely in. Putting on clothes that make you feel like yourself can be therapeutic in that way. You can focus on everything else. And if I feel like running away, well, these are soft and stretchy enough to sprint in!
(By the way, that daughter wears her jeans short now too. Just saying.)
Same jeans, winter version