My favorite group of watches is dress watches, as someone who likes to dress elegantly and whose daily driver is a 190th anneversary edition Longines Master Collection I am really picky with dress watches. Now as the saying goes about clothes, if you can’t dress well on a budget, you can’t dress well at all, we can apply the same logic to dress watches.

Now, as the first edition of the 5 Under 500 series, we will talk about dress watches.  As I am picky with dress watches, I feel the need to set some parameters. The watches must have a leather strap. I loathe people using metal bracelets on dress watches, for me, it makes the watch too sporty. For me, there is not a single watch that uses a metal bracelet that I consider a dress watch, and no, the jubilee bracelet does not make a watch a dress watch. The second parameter is that the watch must be slim enough to fit underneath the cuff of a shirt; if it sticks out like a sore thumb from the underside of a shirt, it is not a proper dress watch. The final parameter is simplicity; a dress watch should be simple; it is possible to play with that statement if you see the A Lange 1, for example, but it is still simple and easy to read.

This is all based on my opinion, as there is no objective truth to this list. With the prefix out of the way, let’s get into the ranking.

5. Timex Marlin

Let’s start with an interesting one. I like to have my watches in the smaller variet,y and especially when it comes to dress watches, this is the Timex Marlin, a manual wound watch coming in at a solid 34 mm, mechanicaly the watch is not anything to write home about, but you can’t expect much from a watch that costs around 200 USD. Design wise it is extremely similar to the Glashütte Original sixties design, which is a good thing as that is an extremely unique and fun design.

4. Casio

The cheapest watch on this list comes from Casio, most people would choose the Casio Tank, but I want to save the Tank design for the next entry. For under 30 USD you can get the MTP-V0002L-1B, despite having an incredibly ugly name the watch is as elegant as you can get for the price tag while still keeping relatively decent quality. It comes in a few different variations. I chose the black version with Arabic numerals and a calf leather strap that has the aesthetic of a classic alligator.

3. Seiko SWR052P1

The Seiko Tank has been a must for many within the fashion scene. I am a bit disappointed by them as they feel rather cheap, but if you are looking at tanks in the sub-500 price range, I don’t think there is a better one. The Casio tank is also fine, but I feel it is too thick for a small tank-style watch. Now I chose the gold pated version as I feel it is more elegant than its steel counterpart, the face of this watch is extremely thin and graceful, as the hands and markers are in this incredible Victorian style with Roman numerals.

2. Seiko Cocktail Time

I have previously talked about the brilliance of the Seiko Cocktail time in the article linked here. I am a big fan of these watches, and despite them being on the upper end of the sub-500-dollar price range, I still think these are great value for money. They are automatic, so they will be on the thicker side, but they just about make the cut. These dials are on the complicated side of things, but I consider them elegant enough to be fair game. You can pick any colorway, but I do consider this one to be the safest.

1. Orient Bambino

This list has been by the books, as there are only so many dress watches at this price that are worth it. The Orient Bambino with the cream dial 110% tops the charts for me. It once again is on the upper end of the 500 USD range, but it punches well above its price. The 38 mm is extremely compact, so it’s very versatile. You could pick any color combination and have an incredible dress watch that catches the eye.

Thanks for reading our first 5 under 500 list, we hope you enjoyed. If you want to read more of our content, then we just released a new article about the Seiko 5-sportsXPepsi collaboration.