You can get a professional looking Tissot or Hamilton - Hamilton might be a bit more than $500 but definitely a good deal overall for what you get, check out the Hamilton Field Khaki.

Tons of great options named already, but just think about what kind of style you want.

Diver (like a Rolex Submariner)? Chronograph (with a timer)? Field watch (Military-Styles simple watch)? Sports watch (stainless steel, simple, durable watch)? Dressy watch (not likely, based off of your description)? Integrated bracelet (sports watch with a more seamless bracelet that you can’t really change)? Digital watch? Quartz or mechanical?

My guess would be some kind of simple sports watch (Traska Commuter or Nodus Sector Sport/Pilot) or maybe one with an integrated bracelet (Tissot PRX or Citizen Tsuyosa). Potentially a dive watch (Glycine combat sub or San Martin SN0111).

Also consider that you can usually get deals on prices. For example, if you go to a store to buy a watch, always ask for a discount. You could get 10-20% off. You can also find pre-owned watches on Chrono24 or from a reputable second-hand dealer online (Jomashop).

Don’t bother with vintage. They are a great option, but risky. I wouldn’t take the risk on my first watch.

I like multiple models from Hamilton in this price range. Swiss made, a brand with good history, quality movements and good looking yet robust, dependable watches. I might consider the Khaki King first.

FWIW, do a web search for best watches under $500 then read articles that provide long lists with pictures and descriptions. They will often categorize the types (as others here have noted) which can help you decide what you do and don’t like. Start making a list. Spreadsheet is what I do. - I’m relatively new to collecting and have several different sheets with Wish List (Grail) watches, Under $1000, and Under $500 sorted. This helps me to go back another day and decide " what was I thinking? Nope!" and cross some off. There are lots of beautiful watches in that under $500 range. Narrow your search using the articles. Oh yeah, then search out a deal on the cost. My daily is a Seiko 5 Sports that retails at $300 and I got for $200. Then I swap bands aloy for colors etc.

metal gshock square

Anyone got recommendations for the same criteria, but in HR and not tech? 🥸

+1 for microbrands. Check out Boldr watches for a field titanium that will look right in with tech.

In addition to Seiko (especially the Presage line) and Citizen already mentioned:

TIMEX Marlin Automatic

Sugess. Arguably the best bang for the buck after Seiko (Seiko, especially the Seiko Presage line, is much better quality). Just got my Sugess moonphase.

Splurge option ($650): Tuseno WINDSEEKER collection.

Hamilton fits the bill perfectly here

Plot twist, OP wants to flex and stand out?

Seiko, Hamilton or Orient

Tissot

I’m surprised Shinola watches haven’t been mentioned

In that price range Tissot, Hamilton, Seiko all make great time pieces with respected heritage and movements. You can also go micro brands like brew, farer, etc.

My recommendation is tissot PRX, it has a timeless design and can be dressed up or down.

Just all depends what you like. Automatic watches are more fun for a first watch IMO, the ritual of setting your watch, date etc. are part of the fun. Quartz watches are also great if you want a movement that requires 0 effort to set and will keep perfect time till the quartz batter runs out. Automatic is cooler to me for a first watch cause it’s all mechanical with 0 electronics, that said, I own watches with both types of movements, it’s all personal preference.

For $500 I would probably get a Tissot gentleman quartz and an Orient kamasu. Both watches would cover all your needs and maybe a small bit of change leftover.