[Recommendation Post] Watches for Groomsmen!

Hello all!

I don't know much about watches but I wanted to buy my groomsmen watches. I like the idea of getting each a personalized watch based on our background and history together but also for their personality. I just started looking but would love to hear your thoughts. Hoping each watch will cost $300-$500.

Let me know what kind of watch you think these groomsmen should get!

  1. Best Man: This is my older cousin. He has always been like my actual older brother. People have told me that I have similar mannerisms. He is loud and has a commanding presence. Always a big man with a big heart that can rally everyone. As a goodie two shoes growing up, I was always boring but this is the older cousin that got me into vices (mild) and I've always had a great time with. He always has my back and he's always been my goto person for all things life. He's an accountant in a large firm and loves to golf.

  2. Groomsman #1: This is my best friend from school. Always the adventurer, he's out spearfishing, diving and doing some crazy adventure. Again, being the nerd that I was, he would try to sneak me out of the house so that we could grab jalapeno ham cheese croissants at midnight and trying to get me to "enjoy life." He's a 4 season athlete yet so humble and always puts himself down cause he never went to a great school. I always tell him he's the hardest working person I've ever seen and I truly believe it. A jack of all trades, he's a youtuber, SEO engineer and owns a fishing side hustle.

  3. Groomsman #2: This is one of two roommates I had in undergrad. We were paired up randomly and have lived together all 4 years of undergrad. To this day, this man knows how to make me laugh with his quirks and is just such a wonderful human soul. He does things by the book, he has a strong moral compass and he's too nice to a fault. A hopeless romantic that is always caught up on small moments. He is also an adventurer and hiker. He is a civil engineer working for the same aeronautical company for the last 10 years.

  4. Groomsman #3: This is the other of the two roommates in undergrad. Lived together all 4 years after randomly paired. He gives off alpha male energy vibes but is such a gentleman and softie. He's the guy that beats everyone at sports and games but never imposes his skill or is cocky. Always tries to play at everyone's level so it's fun. He grew up tight budgeted but has become such a generous man since he started to work as a software engineer after college.

Would love to hear your recommendations on watches based on personalities and backgrounds! Thank you! Writing this has made me feel incredibly lucky to have such a good group of guys throughout my life!