Polo History
Polo shirts were created in the early 1900s by René Lacoste, who was a French tennis player. As you'll recall from my recent tutorial on dress shirts, in that era button-down collared shirts covered up too much of his body and were very uncomfortable playing sports. So he took them to a tailor and had them cut off the sleeves and shortened the length to make them more form-fitting.
He also had them made so that they only fastened down three-quarters of the way to keep his arms cool while playing tennis. To finish it off, he had a crocodile embroidery on the front near the collar as a nod towards his nickname: The Crocodile.
For decades this design was only worn by tennis players. Then in the 1960s, it started appearing on college campuses and then became a staple of the preppy style that overtook Ivy League schools in the 1980s. Polo shirts remained a casual dress code item until recently when fashion designers began experimenting with them as a suit jacket substitute.
When you're buying a polo shirt, buy it in the right fit. The collar should be snug around your neck and make you feel uncomfortable if you try to button all three buttons at once. Sleeves shouldn't extend past your wrist bone but end at least an inch before (as pictured). No one looks good with a polo shirt that fits like a potato sack.
But polos are more than just another closet staple for preppy guys. They're also an alternative to the button-down dress shirts that have been so popular in recent years (and will continue to be). Unlike those, they can be worn with almost any pair of pants you have–dress or relaxed– and they can also be worn in any season.
Three-button polos
Three-button polos are best, but 2-button polos are fine too if that's the only thing you have from The Hill School. To wear on a date with your girlfriend or an interview for a job at GQ, make sure to iron them before you put them on.
Polos are also the best thing to wear if you're travelling by plane and have a layover.* When you're doing that, try to wear something easy to pack and lightweight. It might be nice to show up at your second destination looking like a million bucks, but it'll always be better than showing up in just a t-shirt if there is any bit of rain or cool weather. And unlike button-downs, polos will let you get away with wearing any pants you have, whether they're dressy or relaxed.
Polos are for relaxing and leisurely activities. They are not formal and should never be worn to an interview, any job-related event (even a casual in-office party), or dinner with your family. They should be worn while playing sports or running errands around town and they're also great for travel. They're an easy way to look good without trying too hard and they are perfect for the preppy man who doesn't want to wear a suit jacket when it's hot outside.
How To Style a Polo Shirt:
A polo shirt is an important part of the preppy wardrobe. Here's how to wear one:
1) Don't button all the buttons. The photo on the left shows them all fastened but that's too much for a polo shirt; the only button however many leave a 5-6 inch gap at your chest. Remember that the collar is meant to protect your neck from the sun, so if you leave it open all the way then you're defeating that purpose!
2) If worn tucked in, wear it untucked. The only time a polo shirt should be tucked in is when it's already wearing pants (like with khakis or denim).
3) The fit should be snug, but not too tight. It'll look great with a sport coat or unbuttoned over a t-shirt and jeans.
4) Make sure to get the proper collar style. Polo shirts come in both two-button and three. Three buttons are more traditional, while two looks younger and more preppy.
5) Don't iron it before wearing it to get that preppy wrinkled look. Gruyere, or similar cheese, is also a good way to get polo wrinkles: Just stick it in your pants while you're working out and when you take them off; voila!
6) Don't wear it with a belt (but you can wear one if you have one on khakis or denim). The only exception is if the polo shirt is already being worn over pants.
7) Polos are some of the most versatile pieces in a preppy man's closet, so get one and throw it in there! They work for any occasion, save for the most formal, and they're one of the easiest looks out there.
8) they're also perfect for travel because they're easy to pack and can be worn on the plane.
9) Wear a polo shirt with khakis or denim pants while going out. It's very preppy and looks great with a blazer or sport coat if you want something a little dressier. It's also a great outfit if you're going out to an Irish pub or casual restaurant.
10) Wear a polo shirt with jeans and boat shoes while at the beach or anywhere that isn't as dressy. You can also wear this look with shorts for more of a summer party vibe. Just make sure to leave the shirt untucked. If it's a younger fit, try to make sure the collar shows when wearing shorts or pants.
Polo Shirts Coming Back in Style
While the short-sleeved polo has technically been around since 1925 (see above), Ralph Lauren brought them back into mainstream fashion in the 1970s and has since made them a staple of the preppy wardrobe.
In recent years, polos have been worn by more and more men and they continue to come back into style. They're an easy look that any guy can adopt, no matter his taste level or lifestyle. Some guys are snobs about stuff like this (and wear only brands from the oldest and most prestigious designers; ahem, Brooks Brothers) but those are the guys who have their wardrobe together.
The polo shirt is simple, timeless, comfortable to wear...and best of all, it doesn't leave you feeling like you look like a douchebag. It's one of those items that will never go out of style. The polo shirt is a statement of who you are and what your lifestyle is about. It's professional enough for work, yet casual enough to wear anywhere.
Wearing a polo isn't snobby in any way; it's not anything like wearing expensive designer jeans or shirts, because it looks preppy no matter where you buy it from (and who doesn't love saving money?).
What Not to Wear a Polo Shirt With
Different people have different opinions on this, but you should never wear your polo shirt with khakis (unless you're already wearing it over pants), jeans, or dress slacks. It's always better to wear the polo shirt under those outfits and looks much better worn that way.
Some guys might love their preppy look, but if you're wearing it with jeans and boat shoes then you're doing it wrong. You should only wear your polo shirt with boots or sneakers (never dress shoes) – although some people will argue with me on this point as well.
The important thing is to have fun with it and try new things. If you dig the preppy look, then go for it. That's what fashion (and life) is about: having a good time while looking your best.
A Few Final Notes on Polo Shirts
Just like all clothes for men, there are different cuts and styles of polo shirts. There are heather polos; short sleeve, long sleeve, button-up collars and polo shirts with collar stays that can be removed to give a more casual look.
Some preppy guys wore them with nice jeans or khakis (while others adamantly disagreed) while others wear the polo shirt with chinos or even pants choice, and you should wear what is comfortable for you.
Making sure that the polo shirt fits right is important if you're wearing it with pants or jeans. Make sure that the collar can stand up on its own and that the sleeves are not too short – save those for your golfing ensemble!
If you have a larger chest, choose styles that have a deeper v-neck. If you want a more toned-down look – so you can wear your polo shirt in the office or even work out in it - use an undershirt like this one.
It's best to buy it in navy blue – and never white unless you're wearing shorts (then it can be worn with sneakers or boat shoes).
The Bottom Line on Polo Shirts: The polo shirt is one item that every guy should have in his wardrobe. It's the ultimate staple and a great way to add some style to your outfit without appearing like you're trying too hard. It goes well with khaki pants, jeans or pants of any kind – just make sure it fits right. It shouldn't be too tight but should fit well enough so that the sleeves don't bunch up when you move around. If you're wearing a tie with your polo shirt then choose one in solid colours and simple patterns; stripes look great too (just stay away from busy prints). Plus, wearing one with a tie classifies it as business casual attire (which is the look you're going for if you wear one to work).