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 to anyone willing to listen.

These are not the showy cars or high end luxury brands most people would expect to see. These cars are all about having fun with the family.

Its about going somewhere and enjoying life. This is what the Preppy Lifestyle is all about!

Function and Reliability

Since we preppies value time at our destination, you will not see us buying cars that will break down on the road or not be able to last 25 years if taken care of. We get value from our cars. We look for function over features, quality over exuberance.

Value cannot be understated. The engines in these cars are considered bullet proof and will last a really long time if properly cared for.

Preppy cars are designed to last.

Color and Styling

Silver is always the preferred color or another natural color that will not make the car too hot in the Summer or too cold in the Winter.

SUV’s are preferred over sedans. Preppies value family time and the SUV is perfect for moving the kids and dogs to the beach, mountains, and city for memorable activities. You will also need the room for all the lacrosse or golf equipment.

Convertibles are fantastic for Summer fun for the younger preppy car choice. No one will ever argue driving a sporty convertible is a lot of fun and a great way to visit the beach or country club.

Classic styling is best. Since preppy cars are designed to last and be passed on to younger generations, having classic styling is important.

It is always best to buy a high quality used car over a new one. You will get a lot more value on a used one and will save a lot of money that you can put into maintenance. Preppy cars are always maintained and taken care of extremely well.

Towing is important. Having the ability to tow your small boat to the lake or ocean will provide you and your family a wonderful weekend getaway. Having a roof rack will give you a place to rack your skis, surf boards, or kayak.

Recommended Preppy Cars

Here is my list of recommended cars for preppies. Your needs, driving habits, and budget will help you decide on the best car to get.

Used is always better then new so don’t be afraid of the brand names on this list. These can usually all be found for under $10,000.

Jeep Wrangler, Cherokee, or Wagoneer

Fun Preppy Cars Worth Your Money - Jeep Wrangler
Jeep Wrangler

This is my personal favorite but isn’t considered by most as the traditional preppy car. The reason is mostly due to the limitation of the 2 door wrangler. It just wasn’t practical with family trips.

Today’s 4 door Wrangler is perfect for the preppy family of any age. It can be easily used on snow, sand, and sun (with the convertible or freedom top) and when properly taken care of, will last a lifetime.

If being used for a second car (not your daily driver), then any Jeep wrangler is perfect. I own a 1989 Jeep Wrangler that I use a lot in in nice weather. It is super fun to drive and great for towing the boat to the rivers.

The Jeep Cherokee or older classic Wagoneer are great choices for preppy cars. They look great, are not over stated, and are really fun to drive.

Sorry to say but this is the only American car that made the list.

Volvos – Wagons and Sedans

Fun Preppy Cars Worth Your Money - Volvo
Volvo V70

The Volvo is probably the king of the preppy cars. It is designed perfectly for our lives and is driven by more preppies then any other car on the market today.

The wagon and SUV are the best choices mainly for their traditional look and function. For younger or older preppies without families in tow everywhere, the sedan is a great choice. Bonus points for the Volvo convertible models.

Volvo’s are great in all weather and can tackle off road just as easily as on.

I owned a Volvo XC90 a few years ago and decided to buy another one in the next few years. It was a lot of fun to drive and other then some transmission problems (design problem in the 2004 release), was a very reliable car to own.

Land Rovers/ Range Rovers

Fun Preppy Cars Worth Your Money - Range Rover
Range Rover

I absolutely love the look of the Land Rover and Range Rovers and has been a dream car of mine for a very long time. The classic styling and off road abilities of the model are unsurpassed.

I have always avoided the models here in the US due to the poor reliability these are famous for. If you happen to own an older model and are able to keep it properly maintained, then this would be a great choice to buy.

Subaru Wagons

Fun Preppy Cars Worth Your Money - Subaru
Subaru Wagon

This is another famously preppy car choice. The Subaru off road ability and reliability are incredible. These are really fun to drive and can handle snow and sand perfectly.

My mother has a Subaru for at least 10 years and I drove it a lot. Lots of fun for sure. The car really holds it value more then most other cars on this list (except for maybe the Jeep Wrangler).

This could be the most reliable car on this list and recommended for anyone not wanting to visit your machinic on a regular basis with basic maintenance.

Saabs / Audi / BMW / VW

Fun Preppy Cars Worth Your Money - VW Beetle
VW Beetle

I am grouping these together because they are all very similar in my view. These are perfectly made German engineered cars that are incredible to drive. These all require regular maintenance (more then the average car) but totally worth it as they will last forever and only improve with age.

If you are a preppy family, I recommend the SUV versions of these brands. They are a lot of fun and loaded with function. They will hold the whole family on those weekend getaways and are built to last.

I bought my daughter a 2008 VW Beetle convertible and can tell you this is one of the most fun cars to drive. The cornering and handling is better then anything else on this list. This is not a car to take to the mountains skiing and you are not going to pack the family in it for a weekend getaway. For a day trip to the beach with you and a friend, this is a memorable fun filled day.


Why should you consider buying a preppy car from this list? Because they are all really great cars that will last a lifetime when properly cared for. Getting value in the things you buy is the best way to build and keep wealth. Stop getting car leases and stop replacing your car every few years. Buy quality and love it a lifetime.

There is more to life then buying a quality car that will last. You must really love the car and be able to life your best life in it. The cars on this list are all fun cars that can take you to fun places. Nothing boring on this list for sure but nothing showy.

There are plenty of other cars that could have made the list including plenty of older Mercedes and other German made gems. I also excluded the really hard to find classic sport cars which we all really love. All these cars can be bought used for a decent price and loved for years to come.

What is your favorite preppy car? Let me know in the comment section and don’t forget to sign up for the email list to get notified when new articles are released.