Guide to Dressing Well

Introduction: For the noobs. A primer on Traditional American clothing.

Developing your appearance should be on every young man’s priority list. The style of choice on this blog follows a certain mindset, but it represents a tried-and-true attitude towards men’s fashion. We always complain how today’s generation is is going to crap and how badass those old guys were. So how about we take a few notes from our forefathers instead of the next hottest five minute trend?




Now let me preface this by saying that there are NO concrete rules to clothing. Fashion is subjective. My own personal look may be more conservative and formal than yours so it is your job to decide what you like and mold it to your personality. And even I don’t follow my own guidelines 24/7. What I wear to school and what I wear to the club are two different things. Just because we know how to dress does not mean we can’t let loose and enjoy the comforts of baggy sweatpants like the rest of our friends on campus.

Part of knowing how to dress is also knowing what is appropriate for the occasion. So keep that in mind and happy reading!

Prep is, and always has been, in.

Same goes with the recently named and more conservative older brother of prep, “Trad” (short for traditional), which can also be known also as the Ivy League look.

Brooks Brothers, the king of traditional American outfitting, has been around since 1818. J Press since 1902. Sears Roebuck since 1886. Abercrombie and Fitch (yeah that one, before they started marketing to middle schoolers) since 1892. The list of heritage brands goes on, but they didn’t start out classified as strictly preppy or trad retailers. They were just clothes to the normal person. Most everyone wore suits or sportcoats with a hat on a regular basis.




These are pictures of the lower class in New York City in 1941. Not even rich people today look this cool.

The east coast had a major impact on American style. Prep style originally took hold when wealthy New Englanders would send their kids to preparatory schools to prepare them for the elite Ivy League universities. But it was also our American GI’s from WWII that had a huge influence on trad. When our boys got home from the war, they brought back their chinos, their aviator sunglasses, their bomber jackets, and so on. Then when the stylized mid-century came, the baby boomers’ children (our dads) were starting to grow up and take hold of fashion. Things got more casual and this was the first appearance of slim cut-clothing.

The collars and ties got smaller. The suit lapels and padding became trimmer. The pants grew shorter and socks disappeared. The 1950s to 1960s is known as the Golden Era of American clothing. The Ivy League Look, the clean shaven face of Trad, grew out of this time period. This is when leading sartorial influences John F. Kennedy, Cary Grant, Steve McQueen, Paul Newman, Miles Davis, and James Dean strutted their stuff. Those guys knew how to dress, and no Average Joe looked better before and certainly after this time period.
New York Street Corner 1965

UNC Chapel Hill 1965

In the 1970s and 1980s, prep became mainstream and suddenly everyone started wearing Lacoste Polo shirts with popped collars. Use of color and GTH, which means Go To Hell (a “don’t care attitude” that involves the likes of plaid shorts, patchwork jackets, sky blue pants, and so on) became widely popular. This is when the infamous Official Preppy Handbook came out. Prep style evolved from the 1960s Ivy League look era but most of the same key elements were still there.

Cornell University 1982 via Japanese fashion magazine article

From the 1984 movie Making the Grade

So what do you see on today’s college campuses? The wide majority of us wear our sweatpants, pajamas, cargo shorts, baggy shirts, loose jeans, and flip flops. What the hell happened?

1960s college party. Notice the blazers, the wayfarer sunglasses, the coeds wearing pearl necklaces.

vs.

Present day college party. Notice the huka necklace, the sideways hat, and the man nipples.

Ok, I may have exaggerated a little but you see my point.

The great thing about traditional American clothing is that it’s so damn hard to mess it up. Once you have the basics down, you can pair anything together and step out your front door without a second thought.

And look at the gentlemen in the photos above (except for the one directly on top!) Is that not how you want to look when you’re showing your grandchildren vintage pictures of yourself five decades from now? Would you rather look timeless, as a budding young professional with the world ahead of him? Or disheveled and dated, with those emo ripped jeans and graphic t-shirt that were as embarrassing in 2014 as they are in 2064?




If you’re still in high school then I’ll cut you some slack. But once you get into college and then well into your 20s, it’s best to start dressing like a man should. Your appearance is all that you have in first impressions, to your boss or that hot chick at the bar. We humans are visual creatures. So take pride in wanting to dress better than your peers. It’s time for us to get back to a more classic and timeless style of clothing.