Explore the history behind prep as well as where to find the most iconic preppy clothing for men online from polos to chinos to Repp ties and more. You don’t need to be an Ivy League alum to enjoy ...

Some bastions of preppydom such as Brooks Brothers and J. Press believe the aesthetic will always be at the core of menswear.

Of course, little about this is really new. Ivy style came to the fore almost a century ago, and you can probably already picture the look: soft-shouldered sack suits, hardy oxford-cloth button-downs, ...

A Ralph Lauren polo shirt. A varsity jacket. Khakis and loafers. Are these clothes business casual? Date night attire? Is this a “preppy” look? As it happens, the answer is kind of all of the above, ...

Dressing preppy might be your style. Whether you are going for an effortless chic look to wear to the office or a casual date we are sharing all about the preppy look here. If you want to learn how to ...

We all know what "preppy" means — don't we? If you're older than those in Generation Alpha (anyone born after 2012) you might think of a wealthy person with a particular fashion sense (collared shirts ...

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On a recent Tuesday afternoon, a student of mine wore an attention-grabbing baseball cap to class. The brim was frayed and worn, and the word COCKS was stitched in block letters across the front. I ...

I was never a big fan of “Preppy.” It was always a tad too uptight for me. But, as I said, me= not so preppy (I am not the only one) mostly because I think pink and green look hideous together, those ...