When men’s watches began making the transition from pocket to wrist around the early 20th century, they were often simply pocket watches fitted with wire lugs and a strap. (Prior to this, watches worn on the wrist were considered feminine.) One approach that watchmakers took to distinguish men’s wristwatches (called “wristlets” or “strap watches” at the time) from pocket watches and mark them as purposefully designed products was to make them a different shape.

That’s one reason you see a lot of square and rectangular watches from that era. Today, of course, such angular designs are a lot less common than round watches, but examples such as the three we found below somehow seem timeless. As genuine artifacts, however, they can transport the wearer with a little imagination to another time.

Gruen Precision Quadron Watch

What we like: Gruen’s Quadron watches can often be found for pretty good values, but this particular example looks particularly elegant with its oval dial and engravings. From around the 1920s, it measures 22mm wide by 30mm long in a white gold-filled case (similar to gold-plating but with a thicker layer of gold), and runs on a manually-wound Swiss movement shaped to fit the case. Note, also, that even the case sides feature a nice engraving.

From the seller: No mechanical problems, clean glass, 7/10 overall condition.

Tiffany & Co. Watch

What we like: While the famous New York jeweler is again making watches today, collectors delight in some of the interesting vintage watches bearing the Tiffany & Co. name, some of which were made for the company by familiar and prestigious watch brands. This Tiffany & Co. watch from the roaring 20s looks like something from The Great Gatsby, and inside you will find a manually-wound Swiss movement made by Movado. While the dimensions of its 14k yellow gold case might sound petite for modern standards at 21mm wide by 37mm long, square and rectangular watches tend to wear larger than they sound.

From the seller: This watch has been recently serviced and its case and dial are in good condition.

Hamilton Sekron Doctor’s Watch

What we like: The “doctor’s watches” by Rolex and Gruen are a fascinating piece of early watch history, with a large (for that era) seconds hand occupying its own half of the dial meant for taking patients’ pulses and showcasing improved accuracy. Hamilton was a major force in American watchmaking at this time and had its own take on the popular doctor’s watch. This piece is from the 1930s and features a hand-wound Hamilton 980B movement with a gold-filled case measuring 23mm wide by 40mm long.

From the seller: Case is in very strong condition overall with normal signs of wear from age and use. Dial is in untouched condition with some patination, light spotting, and print loss.