I had some cheap digital watches until I was in tenth grade when I ordered a Hamilton field watch from LL Bean.

A Timex auto from the 70's, my Grandmother gave it to me after my Grandad passed in 78

My first watch was a gifted, cheap pocket watch before I was 10. Probably because I was very interested in my great grandfathers old pocket watch. I recently inherited it and now appreciate it even more. It is an early 1900’s Elgin, hunter style, 18k gold, railroad grade pocket watch. It still works but it’s definitely not something that I’d daily.
I myself have only bought cheap utilitarian wrist watches and no longer care for wearing one.

Omega as a high school graduation present in 1968 from my parents.

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A hand me down Omega from my grandfather on the dad's side. It was crappy, had a $2 twist-O-flex bracelet. I killed it, but it was junk and unrestorable. Got $30 on eBay about 20 years ago. It must've been defective because it got me zero chicks.

Seiko automatic my older brother gave me in 1975. I was 9 or 10.
It was a chunky monkey but I loved it. It had to be a 1971 or 72.

A cheap Timex mechanical wind my dad bought from Thrifty's Drugstore, I think it was when I was in the 5th or 6th grade.

998D25A7-4331-4CFB-8631-E533EFB192D9 by nailheadjr, on Flickr

First watch that I remember my dad wearing, 1951 Bulova Director. It was inoperative for around 60 years until I had it rebuilt a couple years back.
It needed a new crystal, I had them reuse the face and hands “as found” though.

Cheap digital, then a fossil watch with an lunarscape on it, then a pretty good Seiko diver, which is still around somewhere, then my 1680.

Didn’t buy another watch for decades, until the service length for the 1680 got ridiculous.

I am not sure of my first, but the first one I remember was a Seiko automatic.

I've got a Casio F-91W, I like how versatile the alarm function is.

Whatever kind of manual wind “dive watch” K-Mart had on display in an aquarium back in the late 1960s. Probably made in Japan, back when that was considered a bad thing. They were pretty inexpensive or I wouldn't have been able to afford one as a 7th grade lawn mower operator.

That rubber watchband sure developed a stank.

The first watch I ever remember getting was a cheap fake gold case led watch from the mid 70s.
It had a button on the side you pushed to make the time light up red. I still have it to this day but it needs a battery.

The first good watch I remember buying with my own money was a Swiss quartz watch made by Delma. I bought in the early to mid 80s. I also still have this watch but it needs work.

The first automatic watch I bought was a Seiko dive watch I bought in 1990. I also still have this watch but I have not worn it in years.

Timex, in the later 50's. Way before digital.

Timex mechanical. 1962 for my First Communion

I had a Time U-wind it until High School graduation when my dad gave me a gold Hamilton Automatic Dateline. I felt like I graduated and retired from a company at the same time.

Timex, mechanical, about $5.00 in 1957. Yul Brynner was on the big screen and my girl friend's mother bet me I wouldn't shave my head. I did the deed, won the bet and bought my first watch...

My first watch was some sort of cheap digital watch that I got as a kid, maybe around middle school. Don't remember much about it, other than it was black and had a small LCD display.

The first watch I can recall the details of was an Invicta Pro Diver with a basic quartz movement that I got as a high school graduation present from my father.

I’m thinking probably a Timex from the drug store, but I still have the pretty Seiko ladies watch with diamonds my 18 year old boyfriend bought me for Christmas when I was fifteen.

I vaguely remember it being a Timex of some sort, possibly a self-winding, but being more than 50 years ago, nothing else at the moment.

In my former work, wrist watches were a snag (I often had to put my hands and arms in very tight places) and shock/burn (if a metal part came in contact with an electrical circuit) hazard. I haven't worn one in over 30 years. My cell phone functions as a pocket watch. Now that I'm out of the business, I consider a wrist watch from time to time, but it's not a priority.