Look around on chrono24 to see what you like in your price range. I've been collecting watches for over 15 years and can honestly say that in terms of bang for your buck, Rolex is the leader of the pack, if you can get one at retail. Overpaying for one on the grey market is definitely a YMMV enterprise.
Pick one that speaks to you and that you will want to wear daily. It's fine if you don't wear it but if you don't see yourself wearing it, it's not the right watch for you.
Consider the following:
Movement type: (quartz, automatic, manual). Quartz is the cheapest and a few top brands do have some quartz models, but they are generally not considered luxury. For autos and manuals, look at the power reserve (how long it will run without wearing it or winding it). Research the movement (many are made by Swatch and that's not a bad thing, they just own many famous brands). ETA movements are widely used by brands that don't make their own. Some favor in-house movements, for many it doesn't matter so long as it's reliable. ETA movements are popular for this reason.
Complications: date, day, moonphase, GMT hand, chronograph, world timer, etc. These add price and make winding/resetting more of a hassle. Important if you buy a manual or don't wear your automatic daily. (See power reserve)
Size: This is related to style (dress, sport, tool) and trends. The trend of giant watches (>43mm) has waned, and smaller sizes (36-40mm) are more in fashion but buy what you like. Trends come and go. Classics are classics. 38mm is standard for a dressy watch and 40-42 is very common for sport (divers) and tool watches.
Water Resistance: If you plan on it getting wet 100m minimum, even washing dishes. If you plan on showering/swimming with it (I avoid it)...in the ocean (don't, unless you are a serious scuba guy) look for 300m. I use a $40 timex ironman for beach, swimming. Don't swim with a leather strap.
Brands: You will see what the popular brands are on Chrono24. For a site full of watch nerds, er horology enthusiasts, watchuseek is a good one full of helpful people. Don't overlook lesser known or boutique brands, they can offer some cool stuff at a reasonable price. Unless you are buying a Rolex, Patek, or and AP, don't consider it an investment, as it is guaranteed to lose value over time unless it's some highly desirable limited edition and even then, don't expect it to appreciate. You can absolutely find a quality non-quartz watch for less than $1000. The Hamilton rec is a good one. MIDO is a lesser known but highly respected Swiss brand. Seiko is a good Japanese brand. There is also the concept of an 'homage' watch. It's not exactly a knock off, but brands do copy popular styles from each other. Every major and minor brand has some sort of Daytona panda offering. When Rolex introduced the pastel and candy color faces, many other brands followed suit.
Buy what you like in your price range. it's your watch. Most people will barely notice it. I can try to answer any questions, have fun and be careful about getting sucked into a new hobby. I started wanting a swiss made automatic watch for $500, that turned into a collection of watches under $!000 before it got out of hand. Thankfully I haven't reached the most ridiculous levels where I need to worry about security, but I do own a Rolex and a few other 'luxury models"
