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.

Before we go any further, lets clearly understand what is a midlife crisis.

A true midlife crisis and is when a person wants to make drastic changes very quickly in their life.  It’s a form of depression and typically lasts about 3–10 years in men and 2–5 years in women.

Midlife crises can occur in both men between the ages of 40-60 who are overwhelmed with work and family pressure, watching their life speed by wondering what happened to the past 20 years.  They are desperate for a change and a realignment of their younger year goals.

About 25% of people have reported experiencing a midlife crisis, but actually the real number is much lower because the majority of these people actually experiences a midlife stressor.

A midlife stressor is similar to a crisis but the level of depression is manageable.  This is when you revaluate your life and make adjustments to better accomplish your life’s goals.  This is good to experience and the foundation for the list of the best preppy midlife crisis cars list below.

Today the corporate world is buzzing with work process called “agile results”.  This is the constant evaluation of your progress towards the results you want to achieve.  A midlife stressor will realign you back to the results you want to achieve in life.  This is why a midlife stressor (minor midlife crisis) can be good for you.

Why Buy a Preppy Midlife Crisis Car

Simply put, some cars are designed to be really fun to drive, and we all need a little more fun in our lives.

With work and family taking all your time, it is really hard to find time to really enjoy yourself.  That’s the problem the roadster was designed to solve.  It was designed in the 1920’s to be a touring car and to enjoy a leisurely drive in the country.  It was later adapted in the 1970’s to be a sports car and merged the fun of driving with taking a ride in the country.

We all need to work and a lot of us have commutes that could take an hour or more a day.  The purchase of a great roadster would turn those boring drives into a great experience.

Why make it a preppy midlife crisis car? Because the preppy lifestyle love classic styling and take car of things to make sure they last. This is the key to driving a classic car. Buy old, maintain, and enjoy!

If you don’t have a commute, then getting a classic roadster could be a dream you have had for many years.  Maybe you have always wanted to restore an old car and take it on a long road trip.  This is a great way to check off another one of those bucket list items.

If you are a little older and getting ready to retire, it is critical to have something to replace all the hours your career or family were taking in your life (if you are becoming empty nesters).  Having a project car would fit that need nicely.

It is also a great excuse to upgrade the garage and get new tools.  All you Tim “the Tool Man” Taylors give me a few manly grunts.

If you have no interest in mechanics, then maybe get a newer roadster that is easy to maintain but still a joy to drive.  The cost is probably lower then taking on a restore project and you get to spend more time driving.

Sometimes a sports car is a symbol of your success and a treat you well deserve.  It is a reward for years of service both at home and in the office.  There is no guilt in living life to its fullest, especially when you are driving it to work everyday.

Preppy Midlife Crisis Cars

What is a Preppy Midlife Crisis Car?

Preppies are classics and their cars should be too.  It not a true classic in its age, at least it should look like a classic.  For this reason, I focused on the classic look of a roadster.

A roadster is an open two-seat sports car that is really fun to drive.  They are great for touring around town (or the country for that matter) and every fun to race around a track.  They define what it is like to be a man.

Since preppies tend to take car of their cars really well, a 30 year old classic roadster is going to be almost as reliable as a modern car today.  They tend to be very simple, focus your attention on driving and enjoying life.  Exactly what is needed during your midlife crisis or midlife stressor.

The list below are mostly roadsters but there are a few others thrown in.  Some would make a great project car, some great for commuting, and some will even do both!  I tried to pick cars that are affordable but a few could easily break the bank if you are looking for turnkey.

If you are not looking for a roadster and just love preppy cars, check out my article about Fun Preppy Cars Worth Your Money.

The Best Preppy Midlife Crisis Cars You Can Really Afford

Ford Mustang Convertible

Preppy Midlife Crisis Cars - Ford Mustang
Ford Mustang

The car that started the muscle car crazy of the 1960’s and 1970s.  The car was named after the World War II P-51 Mustang fighter plane but carries the logo of the 4 legged kind just to confuse the rest of us.

You cannot go wrong with any generation Mustang.  Older ones make a great project car and the newer ones are great for people who prefer to drive instead of play with things.

Clearly not a roadster (and some could argue not very preppy either) but will appeal to any guy looking to get more muscle without hitting the gym.

These are very affordable options with many options under 10K in great shape.

Chevrolet Corvette Convertible (1/2/3 generation)

Preppy Midlife Crisis Cars - Corvette
Corvette Stingray

No list could be complete without the classic generation 1 or 2 corvette (or 3rd generation if you like the look better).  For me, I love the classic look of a 1967 “vette” in red.

This is the perfect American sports car and is popular all over the world.  This will standup to its European cousins at a fraction of the price.

I prefer the older ones for sure but like the Mustang, any year will be a joy to drive and work on and be the pride in any guys garage.

Newer generation corvettes can be found for a little over 10K and if you are willing for a project, great deals for just a few thousand are available for generation 3 models. Older Gen 1 and 2 can be very pricey but a great investment.

Shelby Cobra (1960’s Replica)

Preppy Midlife Crisis Cars - Shelby Cobra
Shelby Cobra

The Shelby Cobra is in my opinion the best looking roadster every made.  Its classic looks and HP make it an incredible car and a dream of most guys to own.

The Cobra was a joint effort between Ford and AC Cars in England.  Carroll Shelby wanted to combine the English made AC Cobra car with an American muscle car engine.  With some luck, both AC Cars and Ford agreed to the project and the Shelby Cobra was born in 1962.

For under 10 years, Shelby made 3 models called the Mark I, II, and III and rolled into  automotive history.

This is probably the most expensive car in the list often selling for over 20K turnkey but if you are willing to do a little work, I am pretty sure you can find a deal for a little over 10K.


Preppy Midlife Crisis Cars - MGB
MG (B Model)

The MGB is a classic English roadster manufactured between 1962 and 1980.  The British Motor Corporation is famous for several well known roadsters including the Austin, Austin-Healey, MG, Morris, Riley and several other great models.  I also recommend the MG Midget and Austin-Healey Sprite.

I completely love all their roadster models as the perfect preppy midlife crisis car.  Their simple design and open air driving make them a pleasure to look at and drive.  Not a sports car as compared to others on this list, the MGB only put out 95 HP and didn’t have the advances in the suspension to really hug the corners but a great touring car to say the least.

The MG-B car is a bit hard to find in the states but often affordable and around the 10K mark. Expect to put some money into these cars so reserve some cash for repairs and parts.

Mazda MX5

Preppy Midlife Crisis Cars - Mazda MX5 Miata
Mazda MX5 “Miata”

A surprising entry to most people when you compare it to the corvette and mustang.  At around 180 HP in most models, this can hardly be considered a sports car but over 100 million MX5 owners will disagree with you.

Considered the top 5 most popular sports car in history, the Mazda MX-5 Miata is the little brother to the gas guzzlers in this class.  Its design, weight, and power make it perfectly balanced to give you the joy of performance without the extra costs at the gas station. 

Often not given the respect it truly deserves, the Miata is in my opinion the perfect preppy midlife crisis car to buy.  Its low cost, joy to drive, reliability, and easily modifiable make it a preppy guys dream.  All these reasons plus a few more make it the car that I bought and love.

The MX5 is probably the most affordable of all the cars on this list, especially the NA and NB versions. Older, well running NA models will cost just a few thousands with modern NC models just a bit under 10K.

Honda S2000

Preppy Midlife Crisis Cars - Honda S2000
Honda S2000

In its design, the Honda S2000 could be considered the MX5’s twin brother.  Designed to be reliable, fast, and fun to drive, this is a great car to spend your daily commute in.

Honda’s are famously reliable and people know this.  The car was only manufactured for about 10 years in the 1990’s so most models are missing modern safety features (so I hope you have a short commute).

Given the car has about 125 HP, it is not really considered a performance sports car but does look the part.  This is more of a touring car then something anyone will take to the track.

Honda’s have always retained their value and can be found for around $15k. Great value if you are a commuter and don’t have time or money for costly maintenance.

Toyota MR2 Spyder

Toyota MR2 Spyder

The surprising Toyota MR2 Spyder made the list on looks along.  This car was only manufactured for a few years in the early 2000’s and is one of the released in their 3rd generation MR2 line.

With an engine with almost 140 HP, it brings a good amount of power for a roadster with a mid mounted engine.  Only in production for 8 years, like the S2000, it couldn’t compete with the success of the Miata and Toyota decided to focus on other models.

Toyota’s also tend to maintain their value but these can be found for under 10K in great shape. You will need to look hard to find the color and options you want but well worth the time.

BMW Roadster Z3/Z4

Preppy Midlife Crisis Cars - BMW Z3

No list will ever be complete without a BMW.  In this case, there were too many BMW’s to list but can honestly say I love them all and wish I could add everyone.

I try and limit the list a bit, I will say a great preppy midlife crisis car would be any of their older convertibles, especially considering the Z3 and Z4 roadster models.  BMW have been making incredible roadsters since the 1950’s and still make them today.

Not to be left out are the non-roadster models.  BMW makes several series for every price range and if properly maintained will last a very long time.  Given they have been making them forever, it is very easy to find one in any price range.

Z3 models can be found for under 10K but if you want a newer Z4 model, you will probably land around 20K. BMW’s require more money for maintenance to take that into account.

Porsche Speedster (older models)

Preppy Midlife Crisis Cars Porsche Boxster
Porsche Boxster

There is probably no other car that screams midlife crisis then a Porsche.  It is the car most men have dreamt about since the movie Risky Business and Top Gun.

The Porsche speedster is their version of a classic roadster and have several famous models including the 911 and 718 Boxster (with all the models within).  Prices range from under 10K to well over 100K and can fill your desire for a thrill very nicely.

Porsche are expensive but deals can be found on the Boxster base models are just a bit under 10K.

Mercedes-Benz 380SL

Preppy Midlife Crisis Cars - Mercedes 380SL
Mercedes 380SL

A recent add to my list when I saw a picture of the 380SL.  A very classic looking car made in the early 1980s and is often seen in a lot of preppy households.  The classic styling and well cared for mechanics make this a great preppy midlife crisis car if you are looking for a project.

Mercedes are not known for their reliability so this is not your commuter car by any means but a nice Sunday driver to the beach or local store for a little shopping.   If you don’t mind getting your hands dirty or have really good relationship with your local garage, this could be a great car to pick up really cheap.

I very often see these under 10K but expect to put some money into maintenance and reconditioning to bring it to its best. Once up to standards, reserve a bit extra in maintenance.

Jeep Wrangler

Preppy Midlife Crisis Cars - Jeep Wrangler
Jeep Wrangler

The Jeep wrangler is not a roadster or a sports car by any means, but this list is all about preppy midlife crisis cars, and not just sport cars.  The wrangler is about having fun, anywhere, and you can easily tow some fun behind you too.  Its great for a trip to the mountains for some skiing with the family as well as a trip to the beach.

The Wrangler has been in production since  1987 and the CJ models go back to the mid 1960’s.  Great project car if you want to rebuild an earlier model or if you aren’t into that, a newer model can be a worry free joy to drive.

With almost unlimited mods to add, you can easily personalize the jeep to your personality.  With lift kits, large tires, and off-road accessories, you can monsterize your ride for all season driving.

Wranglers hold their value very well but I suspect the costs will be coming down. You can find these under 5K to around 15K for newer models. They are fairly reliable but expect to put money into customizing it to your personality. This is where the fun it.

Toyota FJ40

Preppy Midlife Crisis Cars - Toyota FJ40
Toyota FJ40

For the very serious off roader, nothing beats a Toyota Land Cruiser.  In this case, the FJ40 is the wrangler on steroids’ with its power suspension and simple interior.  It redefines off-roading for the rest of us.

The older models are mostly likely a project car and have been manufactured between 1960-to just a bit over 2000. 

Refurbished ones will go for over 40K plus but deals can be found on eBay motors and other sites for under 10K. Be prepared to do some work but these are so simple, the refurbishing costs should be OK.

Harley-Davidson Sportster or Honda CB 750

Preppy Midlife Crisis Cars - Harley-Davidson Sportster
Harley-Davidson Sportster

Clearly not a car but is on the mind of most guys having a midlife crisis.  Nothing streams freedom and stress free riding then cruising on your Harley with a few buddies.

Sorry to say, Harleys are not cheap.  If you are on a very tight budget and the other cars on the list will not fit in your budget (or driveway), the Honda CB 750 will just might be right for you.

This bike has been in production for over 50 years and is considered by most as one of the greatest bikes every made.  With prices below $2,000, you can easily pick one up and cover it in the driveway or maybe garage.  These are easy to maintain and reliable as hell. My personal favorite is the Nighthawk 750 model in this line in classic black!

Preppy Midlife Crisis Cars - Honda CB750
Honda CB 750
Honda CB 750 Nighthawk
Honda CB 750 Nighthawk

The CB 750 and the Sportster are 2 of the best bikes of all time.  They are classics and simple in their design should remain that way.  They may not be considered preppy but any guy will agree these belong on any list that lists the best preppy midlife crisis cars.

I love the Honda CB 750 and is on my wish list to buy. They are pretty easy to find under $2k and a joy to ride.


The problem with society today is we live in a disposal society.  When something gets old, we replace it with little regard to the possibility of repair.  We get bored with our cars and want something new and shiny.  We prefer to lease and replace our cars every 2-3 years.

This is the difference between a true preppy and someone from the new is better generation.  Classic is better and those who can appreciate it will be much happier spending their money on quality experiences and not a car lease payment.

Over time, the lack of a car payment for just a few years will make affording an extra car easy and fun.  I am not saying you need to keep a car forever.  Just focus your money on quality that can last 15-20 years and you will be happier for it.

This list of cars are mostly quality machines that define what fun driving should be like.  Others are a project of love restoring an old beauty to its prime and enjoying it either by yourself on your commute to work or with the family on touring around town.

Do you agree with this list of preppy midlife crisis cars?  Let me know in the comments below and feel free to share what you would like to see on the list.  If you liked this article, please feel free to sign up for my email list and be the first to hear about future articles.

Thanks for reading and happy driving!