Watches

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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.

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.

If automatic, Tissot, Hamilton and Mathey-Tissot (just to name a few) have a nice selection of well made watches below $500. If quartz, you have lots of different companies in that price range, from Swiss made to others.

Hit up r/watchexchange for some good deals. I'm rocking a Tissot silicum 80 that I picked up for $450 ish. You can really reach upscale with a $500 budget on the used market.

I’ll direct you to Islander Watches, the in house brand for longislandwatch.com. Marc has a bunch of great watches for under $500.

Rolex’s are common in my industry but they scream douchebag to me.

Ow!

This sub is going to be biased towards recommending mechanical watches, and normally I'd agree, but in your case - coming from tech sales - I think you should consider the classic 80's Casio digitals. For less than $200 you could get two (silver and gold) to match anything.

They also dress as high up AND as low down as needed, for example:

https://www.gq-magazine.co.uk/watches/article/ballon-dor-best-watches-robert-lewandowski-gold-casio

Love my Hamilton khaki field auto. The bracelet feels cheap compared to slightly higher end watches but this is a $400 watch.

I love Traska at that entry point. I could see Seiko or Lorier (for smaller wristed folks) as well.

Lorier Neptune IV no date.

Timex Galli S1 is sharp, just under your price point but the finish is better than anything under 1k and better than many above it.

Helios

You def just go for a Rolex. $500 will be more than enough for one. Go to any Rolex store and you can grab one. Enjoy the ride.

Seiko SARX029

A few other microbrands worth looking at are Holzkern, Sternglas, and Lilienthal Berlin.

Furlan Marri is pretty nice. Check it out!

Currently my every day watch is my IWC Chronograph 41, and I often find myself staring at my colleagues Shinola Runwell. He’s from Detroit, so he’s showing love. For around $500, those are really eye catching watches.

Steinhart

Check out Shinola if you want more American involvement in the watch making.

If you want no fuss, always on time (atomic sync or bluetooth phone sync) and solar powered, get a Casio Oceanus S100 or T200 and never look back.

Everyday wear: https://baltic-watches.com/en/collections/hermetique

Dress (scroll all the way through, there are two dress collections in your range): https://baltic-watches.com/en/collections/classic-watches

I promise you nobody in your industry will be wearing one of these, the quality for the price is outstanding, and the design punches above its weight. Can’t go wrong with Baltic.

Little over budget but Sinn is cool, German brand very understated but nice. The 556i model is probably what I would suggest

Citizen NB1050A for the win! Good brand equity, nice movement, JDM (Japanese Domestic Market) model so it flies under the radar, and arguably better than most Swiss watches in it's price range. About 500 bucks.

I am not a fan of Rolex any longer but in my generation it stop for 'successful ' but there are alot of great watches out there . Sorry, but i dont have any suggestions in your price range.

Tissot automatic, whatever looks good. Maybe you can find a Hamilton automatic like a Khaki that you like? Definitely recommend either of those having both.

This is still one of my favorite watches from that price range. Seiko coutura perpetual solar. Gorgeous and a ton of useful functions
https://seikousa.com/products/ssc787