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I've been wearing an Alpinist for the last 10 years. It's nice to look at, easy to read, and the right size for a watch. I wear William Lennon boots, Wrangler jeans, a wool shirt, and a military surplus Italian field jacket. I have many variations of this basic theme, different shirts, t-shirts, jumpers, etc. I buy things that work as advertised and avoid anything with a marketing budget bigger than R&D. My "style" has not been intentional, it has sort of congealed around me as a result of discarding anything that doesn't function as advertised.

I don’t know man… it’s ok to care about your overall look, but it’s also ok to wear an Aqua Terra in a $10 v-neck t-shirt while driving a Corolla. Dressing to impress is fine, but so is not caring about that and spending money on a watch you like looking at.

My Fossil (fishing boat anchor) on my wrist will soon be a gift to my wife's grandson because for me, it is a reminder of a time when I bought it as a gift to myself (to celebrate a number of milestones), and of my utter ignorance.

Moving into an earning bracket of a certain range allows one the luxury of considering what a watch says or doesn't say about you, your income, status, et al. – or at least, for anyone who you think may care to notice.

Dive watch or tool watch or both?

Reading a lot into very little here. 😂

Nope!

I wear my sub with a T-shirt, shorts, and loafers. I super duper don't give a hoot.