Category: Preppy

I am a preppy. I needed several years if self reflection to come to terms and be able to say that out loud. It comes from my prep school upbringing on the New Jersey shows and country club lifestyle. I have spend most of my life hiding from this but I have learned to now embrace it.

I have slightly adapted the preppy style into more Prepster style but I can easily go back and forth. This category will talk about how you can be more preppy, not only in your lifestyle and style, but how to adapt it into your life.

Preppy Midlife Crisis Cars

The Best Preppy Midlife Crisis Cars You Can Afford

A midlife crisis can take many forms in a guy and the results can be really good, or really bad. I think the purchase of a preppy midlife crisis car could be a really good thing for you if you do it right.

Fun Preppy Cars Worth Your Money - Jeep Wrangler!

Fun Preppy Cars Worth Your Money

What are the best preppy cars and why should you get one? Preppy cars are all about 3 things; Sun, Snow, and Sand. If you like these things too, then consider a car on this list! “Class doesn’t shout, it whispers.” All the cars on this list will whisper class...

Preppy Mens Watches

Preppy Men’s Watches for 2019

Having a quality collection of preppy men’s watches is an investment in your future success. It can make a statement about your quality as a man and open doors that you never knew existed. Not to mention, its also very cool and a great improvement to your style if you...