Under $300? Here's my "perfect" watch collection starter kit

I get asked this a lot, usually by my cousins, strange strangers at cafes I frequent, and older nephews (but that doesn't matter): if someone has around $300 and wants to start a watch collection, what should they buy? My answer is five watches, not one. And almost all of them come from Casio and Timex.
Hear me out: both brands make their cheaper watches in huge numbers, and have done so for decades. That scale shows up in the price. You get reliable, dependable quartz movements, long battery lives, and designs that have barely changed — because they never needed to. I could've gone for two watches under $300, but the alternatives just don't stack up in this budget anymore. The Orient Bambino (a usual pick for a cheap dress watch) now starts at $295 on Orient's own US store. That's the whole budget gone on one watch.
I've also included options within options for each slot. The idea is to cover every category of watch first, and then give you some choice within each one.
Digital: Casio AE-1200WH
The AE-1200WH has been lovingly nicknamed the "Casio Royale". It goes for $39.95 (even cheaper with regular discounts). For that you get a world time function with a little map on the display, a 10-year battery, and 100 m water resistance. It's the most watch you can buy for under $40, in my opinion.
If you want the icon instead, the F-91W goes for $29.95, and you can find it for around $22 on Amazon for the bigger part of the year. I'm not personally a fan of the base F-91W anymore, especially since the F-B100W and F-91WF are now out and getting solid reviews. The original has been in production since 1989, and it does little, but I get that's also the point of it. The A168WA-1 is the other option, at $39.95, if you'd rather get a steel bracelet.
The field watch: Timex Expedition Scout 40
My pick here is the TW4B26000, with a black dial, a gray case and a brown leather strap. It's 40 mm wide, 11 mm thick, and also has Indiglo, a date window and a 24-hour inner track. The case is brass, and the crystal is mineral. None of that matters much on a field watch you're supposed to knock around.
The Scout comes in a plethora of other dial and strap combinations. You can pick whichever one you like. The core watch is the same, and it's great.
If you want an alternative, the Casio AQ-S820W series is not a field watch, but for a few more dollars, you're getting Tough Solar as well. That's a neat feature to have.
The diver: Casio Duro MDV-106
The Duro (see above) goes for $84.95, and it almost never sells at that price. It gets you 200 m of water resistance, a screw-down crown and a unidirectional bezel. That's a proper dive watch spec sheet on a budget watch. The 44 mm case is large, though, and the bezel is stiff to turn. It's still the best-value diver I've seen in person, and know of. I can't say the same about the recent value divers though.
The hybrid: Casio AQ-230A
This is the one that makes the collection feel fun in my opinion. The AQ-230A has analog hands and a small digital display at the bottom of the dial. That display handles the seconds, the date and a second time zone, and also runs a stopwatch, a daily alarm and an hourly chime. It's 8.1 mm thin, runs on a battery that lasts around three years, and comes on a stainless steel bracelet. The case is chrome-plated resin, though, which keeps it light at 47 g. Casio lists it for $59.95.
I'd go with the silver-dial AQ-230A-7A, since it's the most classic of the lot. The turquoise AQ-230A-2A1 is there if you want color, and there are gold-tone versions as well that I don't personally like. I have mine with a rose-gold dial though, and it's actually one of the more wearable watches in my collection currently.
The dress watch: Casio MTP-V002
Okay, every collection needs at least one decent dress watch. And hear me out: the MTP-V002 is about as simple as a watch gets. It has a 37 mm steel case, a date at 3 o'clock, and Roman numeral or bar indexes depending on the version. The leather-strap model is the cheaper one, and the bracelet version sells for $53.95 at Best Buy. You're not looking to impress a watch collector. It will look perfectly fine with a suit, though, and that's its job. How often are you wearing a suit? If your answer is "often", you might want to cut out another watch from the collection and get a relatively better dress watch.
If your budget can stretch a little, the Timex Waterbury TW2W14900 is my other pick. It has a 40 mm steel case, a navy dial with full Roman numerals, and Indiglo, for $119. It's out of stock on Timex's US site right now, however.
Taken together, the AE-1200WH, Scout, Duro, AQ-240E and a leather MTP-V002 total to around $300. In practice, you will usually find them under that, since the Duro and the AE-1200WH are discounted so often.
What you end up with is a digital watch, a field watch, a diver, a hybrid and a dress watch. That's every category most people will ever need. None of them are "precious", either. You can wear any of them every day, knock them around, and not really worry about it.
You could also say that a $300 automatic would be a nicer object. Personally, I'd still take these five over it, since they cover more ground, if you're just starting out. My current watch collection has a Seiko SRPK87K1, SPB, and SNK375K, Casio A159WEVJ-2, A158WA-1, the rose-gold dial AQ-230A, GW-B5600DC-1, DW-5600KHS25-1, this G-Lide GLX-5600 model, and a newly obtained JDM Citizen Attesa CB1120-50C. I've not spent above 30,000 INR/$313 on any of these watches. I don't think I'm ready for my "big" watch yet, and I'll wait until I am — big-boy watches are expensive expensive. Well, relatively at least. I am eyeing a "The Citizen" model next. If you ask me, they're probably some of Citizen's best work to date.
My final note, I promise: once you've worn all five of your new watches for a while, you'll also know which kind of watch you actually want to spend more money on next. My endgame is shaping up to be a 38-ish mm case size, titanium and solar — easy to wear, easy to maintain, easy to forget. A friend of mine figured out he likes divers, so that's his endgame. It's all extremely subjective!
Good luck with your new collection, if you do actually plan to start one! If you have any alternatives in mind, feel free to drop your recommendations in the comments.
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