Denim Confessions! The Worst Jeans I Ever Owned

I know what you’re thinking. There’s no way that I, a denim blogger, could ever have owned an embarrassing pair of jeans. You probably assume that I came out of the womb in a pair of dark denim skinny jeans. Alas, I wasn’t born with a sixth sense for denim style. It was cultivated and nurtured over many years, and not without it’s share of serious missteps.

Through my interviews and conversations with other bloggers for our Denim Style features, I realized I’m not alone in my shameful denim past. I thought it might be fun find out what kind of crazy, ill-fitting, scandalous, and just plain unattractive  jeans some of my favorite and most stylish friends have owned at one time or another.

I suppose to kick things off, I’ll go first:

The worst, most embarrassing jeans I ever owned were from Abercrombie & Fitch, that I wore religiously my junior year of high school, circa 2003. These jeans (a pricey $70 at the time), were ultra low-rise, dark denim and had suede laces where the zipper fly is supposed to be. They also lacked pockets on the derriere (this was before the days of tunic tops), and had a 7-inch slit at each ankle, so I could show off my platform Jack Percell tennis shoes from the side. They were trashy, age-inappropriate, and I loved them.

Katy Atlas, Sugar Laws:

“I had a pair of denim overall shorts.  From the Gap.  That I wore – in college.”

Grace Atwood, Stripes & Sequins:

“The worst pair of jeans I ever owned was my first pair of jeans.  Bought in the third grade, I had begged my mother for weeks for them.  They came from Marshall’s and managed to incorporate three of the worst trends from the late eighties all at once:  High waist, acid wash, and, wait for it… neon tie-dye.  Over twenty years later, they still haunt me.”

Alicia Lund, Cheetah Is The New Black:

“Well I used to love really baggy, super long denim (and still do). I was always dragging the bottoms of my jeans in high school and I had a pretty crazy pair of super bells without back pockets. I hate denim without back pockets now (they can be so unflattering), but I still love flared denim!”

Jordan Reid, Ramshackle Glam:

“The ugliest jeans I ever owned: a pair of way-too-big men’s jeans that I picked up at the Salvation Army in 9th grade. They were sorta bell-bottomed, but so enormous on me that you could barely tell what shape they were…they mostly just looked huge and messy. I ended up wearing them constantly during a summer I spent teaching English in Costa Rica, and after two months of nearly daily wear they were mud-caked and ripped up to the point of nearly falling apart. So they were ugly, for sure, but they were also one of my most treasured posessions for many years, because of the memories that they held. Today those jeans are my very special DIY Project Pants, and as such have accumulated countless more stains courtesy of paint, glue, and what-have-you. You’d never catch me wearing them in public…but I love ’em anyway!”

Emily Knightly, Sugar & Spice:

Boyfriend jeans that didn’t taper, and were too long, and in a weird blue somewhere between indigo and stonewashed.”

Sonia Gupta, In Pursuit Of Style:

“Wide-leg overalls from Old Navy that I wore in the ’90s.”

Thank you so much to everyone who emailed and tweeted their denim confessions. Did you ever have an embarrassing denim moment? Share it in the comments!



  1. November 10, 2011 / 12:55 pm

    Jnco Jeans in very wide, very stiff black denim. (What ever happened to that brand…?) Since I went to a private middle school and had to wear uniforms everyday, I practically wore my Jncos every weekend for a year until they completely fell apart. This, of course, was before I discovered real fashion, lol.

  2. November 10, 2011 / 4:25 pm

    i had jeans in college that laced up the front instead of a zipper, and a pair that you pulled on, with laces on the hips. it was horrifying, to say the least. 🙂

  3. lazypadawan
    November 10, 2011 / 10:31 pm

    In the ’80s, I had my share of acid wash but they really weren’t so bad. There was a long denim skirt with an ashy/black wash that was pretty cool for 1987. I’m not ashamed of it! However, I had a denim jacket and I wrote all kinds of crap on it with a Sharpie. I think I also had a crummy pair of baggy jeans full of holes that I bought at a thrift store. For a school project, I took a pair of cutoffs from a thrift shop and put safety pins and little plastic spiders on them.

    Back in the ’90s, I wore a set of overalls that made me look like Cotton Eye Joe. I’m sorry to say I was in my 20s at the time.

    When I was overweight, I wore a lot of dude denim. I sold them as soon as I dropped enough weight to squeeze into a size 32.

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