The Preppy Watch

  The most preppy watch you could wear -by far- is the classic Timex.

Many would point to the Timex Weekender as the one to get. While I will not dispute the prep cred of that watch, I feel that the Timex Croco Strap Watch is the more trad of the two (pictured below).

This watch is superior to the Weekender due to the fact that it features Roman numerals. If you look closely at this old poster (shown below) you will see that Roman numerals on a watch are cited as being preppy.

Once you receive your Timex Croco Strap Watch simply remove the leather strap and then replace the spring bars without a strap. Then purchase a few 20mm grosgrain watch bands and slip them through the spring bars (demonstrated below).

There are hundreds of striped watch bands to choose from in every color combination imaginable. Many traditional clothing outfitters sell them and eBay is a good source for them as well.

These Timex watches are very inexpensive ($35-$50) and thus understated, adding to their prep credentials.

And finally, here are a couple of photographs for those preps that prefer the Timex Weekender (shown with grosgrain striped bands, of course).