Preppy Lifestyle – One Mans search for Happiness

Back in 2016, an over weight, un-styled, middle aged man who desperately needing some passion in his life, decided to change his life for the better.  This transformation focused on his preppy lifestyle he once had in his younger days, and his life has never been the same since.

A lifestyle change is different then your new years resolution on losing a few pounds or spending less time at work and more time with the family.  Its about knowing what’s important to you, and committing to changing your life to make sure these passions become part of your life. 

A lifestyle change is all about focusing on the habits and not the results.  Its about knowing who you are and what you want, and these are probably the 2 more difficult, but important, questions you will ever ask yourself. 

Ask yourself what you can do to make yourself happy.  This cannot depend on other people’s approval, respect, or expectations.  This is something you do for yourself.  For me, it was looking inside and having a vision on what I want everyday to look like.  For me, I loved living the preppy lifestyle more then anything.

What is the preppy lifestyle, and why did I fall in love with it when I was younger?  For me, it has nothing to do with money, that’s for sure.

What is the Preppy Lifestyle?

The preppy lifestyle is about 4 things:

  • Healthy Lifestyle
  • Buy quality and always look your best.
  • Minimalizing stuff, Maximize Experiences.
  • Spend less time at work and more time doing what you love

If you can relate to this list, then maybe the preppy lifestyle is for you?  Notice I said nothing about colorful polo shirts, boat shoes, sailing, or playing golf at the club.  What you choose to wear and choose to do is all up to you, and should always make you happy.

If you are recalling the 1980’s “The Official Preppy Handbook”, you are not that far off.  But this is not me, and probably not most people anymore.   Lets dig into each one.

Healthy Lifestyle

If you are tired how you look in the mirror, or will never take your shirt off in public, then you are not alone.  But, it doesn’t have to be this way.

Living a healthy lifestyle is all about choosing what you do.  You can choose to eat well and exercise, or you can choose not too.  The key is to make the decision to choose an automatic habit, then there is no choice and the action becomes automatic.

I choose to eat well, do intermitted fasting (because it was easy for me, I don’t like breakfast anyway), and exercise every morning.  That’s it, just 3 habits I need to do, and do them early while I have an abundance of will power.

This is easy and not only is for people looking to live the preppy lifestyle, but for anyone.  Change the 4 things above to match what you love and what’s important to you, and call it anything you like, the process works the same.  I choose the Preppy Lifestyle because I needed to buy all new closes after dropping 50 pounds and going from a XL (sometimes XXL) to a medium in all my clothes, and Vineyard vines fit my new body perfectly.

Buy quality and always look your best.

I hated to spend money on clothes and I was the anti trend dad mocking anyone who bought into that lifestyle.  Then I heard a quote that changed all that.

I don’t design clothes. I design dreams.

Ralph Lauren

This little saying put it all together.  If I want to life a certain lifestyle, then I need to dress like that lifestyle.  Its not a costume, but it’s the real me and the only think I would really feel comfortable wearing.

The great thing about high quality clothes, especially preppy clothes, is it is considered clean and classic.  Both things that closely represent me.  Buying preppy clothes will never go out of style, and therefor should be made well to last many, many years.

"Life's too short not to be stylish"

Minimalizing stuff, Maximize Experiences.

This is all about the 3 M’s; Minimalize, Maintain, and Maximize experiences.  Its about removing the clutter that sucks your time away from doing the things you want to do. 

To be a minimalist, you simply stop buying the stuff you don’t need.  People buy things to make themselves feel better, but minimalism is all about spending money on Doing the things that make you happy.  IT is easy to break the spending habit too.  Every time you are feeling down and have the urge to buy something, go out and have a good time instead (restraint, park, or friends).  Get the picture?

Since we buy quality, and only the things we need (and not want) then maintaining those things will make them last and be important to us.  Buy nice shoes and bring them somewhere to be fixed.  By a nice car and make sure it will last 20 years.  Buy a nice watch and pass it down to your kids.

When maximizing experiences, this simply means getting off the couch, turning off that TV, and go outside with friend and family.  Life will not come to you, you need to go out and meet it in the real world.

Focus on these 3 things and your life will be fuller, as well as your bank account.

Spend less time at work and more time doing what you love

If you are spending less money, then you will not need to spend as much time at work bucking for that next promotion.  You can spend that time doing the things you enjoy.

Learn something new, volunteer doing something you love while making new friends along with it.  Spend time on a hobby or making memories with your family.  Time is the most valuable resource you have, spend it wisely.

Money and Comfort

You have heard the saying, money can’t buy everything.  Well, that may be true, but it can buy comfort, and that is important.  But do you need money to be comfortable?

The answer is clearly no.  You can be comfortable sharing a 200 SF room or living in a 4,000 SF beach house.  It starts by being comfortable with yourself, then making small changes to your space to better reflect who you are inside.

I love to use Pinterest to look for style and home design ideas that fit my personality.  Once I get an idea, I buy used over time until my life fits my ideas.

By buying used, I can save my money, invest it, and have it grow and help provide for my  lifestyle.  I have written many articles about how to manage your money and enjoy the life you dream, and you can find them HERE.

Finance Books Every Guy Should Read

My story

So how did I go from over-weight and un-styled to writing this article?  That’s what this whole website is about.  I take all the things I learned over 4 years and created over 100 articles teaching you all the things I learned and did, from eating right, spending wisely, and learning all I could about who I am and who I want to become.

It all started with one of my first articles, Intermittent Fasting Lifestyle – How I lost 40 Pounds in 4 Months.  In this article, I talked about my 3 phase approach; Eat healthier, Exercise, and Intermittent Fasting.

I then started to focus on enjoying my new life.  I learned to drink scotch (Best Scotch for Beginners), became a minimalist (Living a Less Stressful Minimalist Lifestyle), and learned how money really works (4 Money Mindsets on How to Build Wealth).

Reading became a priority for me and I would also read several books a month, either physical ones (I have a great home study) or audiobooks from Audible.  Then I would pass along the things I learned and recommend my favorites.  You can find these at 10 Best Self Help Books for Men, 12 Business Books Every Guy Should Read, 20 Gentleman Books Every Guy Should Read, 15 Finance Books Every Guy Should Read, and 25 Classic Books Every Guy Should Read

Knowledge is all the power you need to change your life, and its free!

Why did I pick the Preppy Lifestyle?  I didn’t start off that way.  I started watching YouTube videos and I would binge on AlphaM videos and adapted his style.  Then over time I realized I wasn’t fully comfortable being a mini AlphaM guy.  My Pinterest account showed me I was a true preppy, with strong geeky parts buried deep inside.  So I just let it out.  I dressed preppy but did very geeky things.

I learned to play chess, got back into Dungeon and Dragons, and carry my laptop with me just about everywhere.  Also, I’m learning to cook really well and do anything to experience something new and exciting.  This is the purpose of life and should not be missed.


So this is my story in just about 2000 words.  I went from over worked, over stressed, broke, and boring to someone who now enjoys every day of his preppy lifestyle.  I still have a full time job but I enjoy what I am doing.  Everyday I spend my free time reading, learning, and experiencing new ways to enjoy life.

Anyone can tell you I’m not special in anyway.  My only super power is I never give up.  If I set a goal for myself, I will not stop until I reach it.  You can do this too if you can be just as committed to your goals, you too can achieve anything you want in life, no matter on where you started in life.

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Thanks for reading.