I'm the only one who did proudly wear the dreaded MOM jeans back then?:-) But I was tall and thin, so think they flattered my body showing off my thin waist -which I don't have anymore...:-(.
Before I discovered my fave look of the the flared hems with pointy toed western booties/shoeties or heels in the early 00- there were some bootcuts/flared hems (which I'm not 100% sure that they were always the PPl:-( and were wraped into snow boots) . Oh and not to forget the classic and boring straight cuts(worn with flatforms or wedges), some cords + real trousers with heels.
And there always was the knee high boots (prefferable the riding boot style) with pencils/denim skirts when younger- one of my all times signature style (before the booties era) as I have had great legs.

what La Pedestrienne said....also, i'm pretty sure that until the recently i never practiced PPL....

Bootcuts, bootcuts and more bootcuts. That was me before skinnies. And before PPL so they were all just a little too short on me too. LOL

I LAUGHED at your responses. Thank you

Shevia, I used to just let mine drag in the snow and rain! I remember we all had huge salt stains on our hems back then. I guess the boots kept my ankles warm.

Jessikams, I totally remember that from the early 00’s! It was kind of weirdly trendy to have too long bootcut and flare hems that you tread all over and tore up. Man, my mom hated that look whenever she saw us in it. I remember my sister and I were once home for a visit and she forced us to let her hem our jeans! Lol.

Bootcuts or leggings (shudder) because I was schlepping 3 kids around and didn’t really care or worry about how I looked or if my pant hems were wet. I was more worried about my kids.

Diana and Jessikams, yes, I think the wet, ratty, chewed-up hems were very much part of the look for a while. If your hems weren't shredded in the back, your pants were too short.

To be honest, I think boots of any sort were very un-cool when I was in middle and high school; I don't remember anything other than sneakers as a teen, even when it was freezing (and have frostbite damage on one toe to prove it...).

I remember how weird it seemed when bootcuts came back in--was it in the early 90s? I didn't wear jeans that much, but they were usually straight leg or slightly tapered. Funny, I don't remember that well either. I will have to look at old photos.

I wore regular cotton pants--chinos--and trousers more than jeans.

I didn't like skinnies at first. I have skinny legs and I thought they made me look like an ice cream cone shape. What I called my first pair of "skinnies" most would call straight leg today. Now when I wear straight leg I feel more comfortable but also don't think I look as modern.

I do remember the joy of my first pairs of Gloria Vanderbilt stretch jeans--and they were corduroy as well. Such great fitting jeans! They must have been straight leg.

My first go-round with the skinny leg was in the '70s during the disco era. They were 100% cotton, so really skinny, and they shrank to fit--ever tighter! lol
You had to lie down on the floor to zip them up. My sister and I had to sneak them into the house. Buy them on sale, slip them upstairs, then smuggle them down to the jeans pile in the laundry in the basement, so mom wouldn't notice them.
Then, when she saw what we were wearing as we headed out to school. "But Mom, we CAN'T return them! We bought them on sale, and they've already been washed!" Sneaky little so-and-so's. My poor mother, not sure how she survived our teen years.

I was so glad when skinnies made a comeback. They were my prevailing silhouette through the 80s (and 90s).

I may have a stash of them deep enough to last me a decade or more currently sitting in my closet right now. I hope they never go away, because I will be heartbroken if I can't find them in stores.

I wore flared Jean's in the early aughts and hated the wet hems (I refused to hem them shorter just like you). Skinny jeans made their resurgence as I was going through a breakup from an ugly relationship that left me trying to "find myself", and they just resonated with me. They've become my default silhouette because I am the epitome of the opposite of grace that trips over extra fabric around my ankles (true story). Long live skinny jeans (but I do enjoy seeing other silhouettes on you guys).

Directly before skinnies I wore bootcuts, as suggested by you Angie!!

Before that? maybe straight legs? Hard to remember, though I do remember tapering some second hand ones in the 80s

I exclusively wear jeans handcrafted by one Mr. Levi Strauss from 1853.

...and yeah, he charges like a wounded bull.

Maybe I should try some skinnies. I always wear slim straight, because muscled calves and tighs.
Before the slimmer pants I wore wide legs. Fitted on the hip, and from there the legs got wider. Not too wide, because then I got swamped. I don't like bootcuts. Also I wore trousers with pleats, like they had for male suits.
On my wedding I had a pantsuit with pleated trousers, but I had a waist and could tuck.

Most of my jeans are skinny or high-waisted. Though they are really messy to wear on rainy days. However, I am most comfortable with them!

Soggy hems and I don't even think it crossed my mind that one could look fashionable and stay dry at the same time. Hems got stuffed into ugly snow boots and then immediately changed once inside.

It's hard to remember. I do vividly remember wearing bell bottoms up until 6th grade. Then in 7th grade it was straight legs (GAP jeans and corduroy) as well as khakis (preppy phase). I wore those through high school and into college. I remember tucking my jeans into cowboy boots and later moon boots.

Post-graduation and my first job, I lived in skirt suits, always with pumps. Big shoulder padded jackets. I also lived in a pair of high rise black trousers which I held on to for years before finally conceding my waist was never going to be 23 inches again....

Then there was the long bleak dark years in the 90s when I hated all the styles and suddenly jeans were my enemy; this was when I was having children and was a SAHM. I wore a lot of khakis that weren't all that flattering. And stirrup leggings!! Anyone remember those??? And lots of sweat pants --- you'd call them "joggers" today -- but they were pastel and had a matching shoulder padded jacket.

When I re-entered the workforce in late 90s, my uniform was black wide leg high waisted trousers. I had one pair that I duplicated 3x and just wore those with everything, including chunky black footwear. I also had a pair of grey flannel bootcut pants from the GAP, which was my weekend uniform. Also still wore skirts back then -- including midi length. Those days I had very little $ to spend on fashion so my wardrobe was quite small.

I still hated jeans through early 00s -- the low rise trend was not for me. YLF got me back into jeans over a decade ago. Straight legs first. And I still fondly remember the PPL COH flares -- those have been long retired. Wouldn't mind finding a replacement for those. Then skinnies - which I prefer to straights.

Still wasn't an every-day jeans wearer (preferred ponte knit pants).. until now!!! The difference? HIGH WAIST! I need a high waist!!!! I hope high waisted styles never go out of style again....

His moustache free goatee freaks me a bit, but he is the master of his domain.

I missed the last go-round of bootcuts, finishing a diss and starting a kid. But Angie, your line “I couldn’t not wear them at the right length” makes me laugh. I’m pretty sure I would’ve concluded that if it made trouble by getting soggy, then it wasn’t the right length. That’s why you’re a fashion consultant and I’m not. Form pretty much always comes after function for me.

What a fun post, taking a stroll down memory lane!
'80's-Levi's 501's for sure! I also remember having a pair of trouser jeans with pleats I thought were pretty cute, lol. But my prized possession was my Guess Jeans (I think they were straight legs.)

'90's-You'd think I did a lot of drugs, but I barely remember anything about the '90's, lol! I actually hated the music, too. I think I wore a lot of leggings and cute going out clothes so I don't think jeans were that important to me. Somewhere either in the late '80's or early '90's we wore slim leg jeans, folded the bottom of the calf in and then rolled them up a couple of turns.

00's-I think I wore straight legs? I bought a really cool pair on Rodeo Drive in Beverly Hills for $20--major score! They had hand painted roses and Japanese writing going up the legs. Unfortunately it wash off (sad face emoji.)

I remember the exact moment a friend showed me premium denim in 2002! Shortly after, I bought my first pair of boot cuts. I only liked them with heels, so didn't wear them a ton. I don't remember exactly when I got my first skinnies, but I love them...although as comfy as they are I'm getting a little bored with them. On the other hand, the versatility can't be beat!

Yep, bootcuts folded up into snow boots, if need be. Or skirts and tights with combat boots.

Bootcuts and soggy hems. Ugh! Never again. Never ever again.