Another poster yearned for the 2000s preppy era of argyle sweaters and tailored dresses. The poster @mmarkroberts said he thought the end of preppy fashion was with boat shoes and Vineyard Vines T ...

The sudden, urgent desirability of khakis and rugby shirts. If you're a dedicated follower of fashion, you may have noticed all of these signs, all suggesting one thing: preppy style is back. It's not ...

Although monograms largely fell out of favor in the post-preppy era, they’re now being rediscovered by women in search of a signature style statement. Sets of initials are cropping up on shirts ...

However, if there was one renaissance we didn’t see coming, it would be that of the preppy style that was also a major style factor of the early aughts. The era gave us Gossip Girl, the heyday ...

In the late 1990s and 2000s, there was yet another iteration of the trend: "preppy" became synonymous with "basic" or styles that were more-or-less uninspired and in mainstream trends. In that era, ...