Wow - what a wild trip down memory lane! At least what I can remember of it - lol. I distinctly remember my first pair of jeans :two-tone denim where the legs are different from each other as are the front and back. I was quite the little fashion plate with those pants. I had all sorts of jeans - every bad permutation of studs, patches, pockets, etc . I sewed a lot of my clothes though during the junior high year and wore a lot of wrap skirts. Oh dear. I also remember wearing cords more than denim jeans during the middle school-high school years.
High school for me (mid to late 70's) : we wore Tribal dress pants a lot. I have no idea why, but I had them in several different colours. Jeans took less of a place in my closet.
University - I was in Clothing & Textiles, and we dressed up. Only "dressy" jeans. With permed hair. My first job out of uni was with Western Glove Works, the company who makes Silver jeans, and is the licensee for Victoria Beckham's line of denim, among others. Never wore them much though as they weren't allowed at work, oddly enough. That was the 80's though, and I am quite sure that isn't the case now.
Between then and now, it's only been in the last say 8-10 years that I've really worn jeans a lot. Never to work, that much I do remember. I remember when skinny jeans first hit the stores, and discussing with my friends how horrible we thought they were. Little did I know they'd become a mainstay in my wardrobe shortly after, and are still today. They are my preferred style as I like a streamlined and slim lower half visually. I've experimented with all cuts and silhouettes though - but always return to skinnies.
One thing I find interesting: I've invested serious $ on other items in my closet: coats, handbags, jewellery, watches, blazers etc - but I have NEVER bought a pair of premium denim. I think it's fear of not getting them right - fit is so hard to get on jeans and some stretch and some don't. I may be breaking that barrier in January though:)