The Comprehensive Guide to Becoming a Preppy Guy

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Let’s start with a confession:

There is no way a comprehensive guide to becoming a preppy guy can ever be written.  If it does, it will probably be on the same website with articles on “How to Know Everything about Computers,” which, in turn, will probably be next to a definitive article called “The Standalone Manual to Understanding a Woman.”

I think you get the idea.  Preppy is beyond definitions, classifications, and categorizations.  Moreover, it’s a dynamic movement, an ever-evolving trend.

So, consider this a guide to catch the trend, where you’ll learn enough about how to be preppy to look, think, and behave like a preppy guy without a shadow of a doubt.

When adopting the preppy lifestyle, there are three things to consider: the clothes, the look & feel, and the attitude.

preppy guys

The Clothes

1Brands.  Choose name brands.  While some may have a West Coast, East Coast, or classic look, they can all be coordinated to create a preppy style.

2. Shirts.  Think of Rugby shirts, stylish surf-inspired polo shirts, and chinos.

3. Colors.  The rule with colors is to choose colors that match your hair and skin.  If you’re a redhead, for example, you will look better with green.  If you have blue eyes, wear lavender.  Popular colors are yellow, Nantucket red, lime green, navy or sky blue, and pink.

4. Belts.  Lean toward classic belts, and choose tan or light browns.  Choose between leather and canvas belts with leather tips.  Leather belts are for formal occasions while canvas belts are for times when you want to look casual.  Avoid thick belts, belts with big buckles, or belts with studs.  These are tacky.

5. Bottoms.  Shorts are very popular, especially men’s cotton Poplin shorts, Derby shorts, and Catalina Shorts.  For pants, consider Cal pants or regular cotton men’s pants.

6. Footwear. Preppy footwear could be leather flip flops, leather moccasins, or top siders (aka boat shoes.)

The Look & Feel

This is a little tricky to describe.  It’s not about what you’re wearing but about the general visceral reaction people have around you.  So, we’re talking scents, glasses, and hairstyle.

The scent

You want to be known for a single scent.  After you pick the scent that works best on you, use it sparsely, not liberally.  Pick that scent for your cologne, deodorant, aftershave, body wash, shampoo and conditioner.


If you wear glasses, choose rimless glasses and clean them every single day.  Dusty glasses do not look good, and it’s easy for glasses to collect dust.  Avoid dark rimmed glasses—they look geeky or punkish.

Hair styles

There are two alternative ways that you could do your hair.  One is to have the intellectual look—long hair, shaggy, or fluffy. This works if your hair falls to the sides and back easily.  However, if your hair tends to grow into a mop, then choose the crew cut style popular in the 1950s. Avoid the shaved back and sides look as if you just got discharged from military service.  Avoid weird hair colors or even highlights.  If you have to use gel, then do it with a light touch.

The Attitude

Preppy guys are smart, athletic, and socially adept.  Think Ivy League culture here. Your attitude should reflect those of a classy guy.

Here are six tips:

Tip #1: look fresh and neat by

·  Cleaning, trimming, filing, and buffing your nails.

·  Using lip balm if your lips tend to get chapped or cracked.

·  Keeping your hair combed.

·  Staying clean shaven.

·  Keeping clean teeth through regular brushing and flossing (twice or thrice a day).

·  Maintaining fresh breath. (Stay away from garlic and onions, and use breath fresheners.)

·  Avoiding tattoos or piercings.

Tip #2: look healthy by

·  Getting a light tan

·  Drinking lots of water

·  Taking multivitamins and minerals

·  Avoiding fattening foods that give you a gut

Tip #3: look athletic by

·  Participating in team sports like football, polo, rugby, or lacrosse.

·  Or participating in individual sports like horseback riding, track, or golf.

Tip #4: look socially-adept by

·  Being outgoing, even if you’re slightly shy.

·  Being friendly, nice and cordial.

·  Smiling.

·  Sitting up straight, not slouching.

·  Sanding up straight, like you know you belong in the room.

·  Avoiding childish, annoying, or irritating behavior.

·  Avoid being crass.  Regardless of how well you’re doing financially, avoid bragging about it, including talking about how much you paid for something.

Tip #5: look intellectual

·  Staying aware of current events.

·  Reading literature.

·  Attending Shakespearean plays.

·  Listening to classical music.

Tip #6, look classy by

·  Avoiding profanities and crude humor.

·  Being considerate and courteous to others.

·  Avoiding hats and dark glasses indoors.

·  Texting when you’re with friends at a dinner.


While most people think preppy is about clothing, you also need to look as if you belong in the stylish clothes you’re wearing.  So, preppy is also your overall demeanor and attitude as well.  Preppy guys have a lot of class.

Radhe Gupta
Radhe Gupta is an Indian business blogger. He believes that Content and Social Media Marketing are the strongest forms of marketing nowadays. Radhe also tries different gadgets every now and then to give their reviews online. You can connect with him...

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