I think part of the answer is the wonderful power of contrast. Plaid means business — or at least retirement — but shorts definitely don’t. So plaid shorts add a sort of playful attitude to the maturity of plaid patterns. And this can be a great trick to play, at least compared to other fashion-powered contrasts.

Plaid lets you start off with a premise of maturity, and that’s a great asset. When you’re wearing plaid shorts, people know you picked an unusual pattern, and that you added it to a more youthful article of clothing. That mature pattern means that you know what you’re doing — that if they think you’re weird, the joke’s on them. Unlike other similar fashion choices, plaid shorts don’t add the risk that you’ll just look weird: if you’re wearing plaid, you must know what’s up.

Plaid has other advantages, as well. It’s a pattern that has been around for a long time, so if your new plaid shorts catch the tail end of one trend, you’ll be on the vanguard for the next. And since shorts are always in style for their utility and comfort, plaid shorts will still be good to have even if you’re not showing them off so much.

The best thing about plaid shorts, by far, is that their recent popularity has encouraged many more designers and retailers to pay attention to them. If you’re in the market for ,plaid shorts you’re likel to find plenty of stores with a great selection of shorts that are perfect for your needs.

When you pick out plaid shorts, it’s important to pay attention to a few factors. Comfort is almost a given — most are made with fairly nice material, and they’re roomier than most legwear. So the main issues are price and pattern. As for price, the best bet is actually to aim for smaller stores. Unlike the big companies, they tend to attract people by having a great selection at a great price, rather than having a well-funded marketing department. Pattern is another matter entirely. Plaid shorts come in all shades and (plaid-based) patterns, so the best thing to do is just see which ones you’d be comfortable wearing in various situations: imagine wearing your plaid shorts to a party with friends, on a hike, on errands, etc. If it looks sane, go for it — you’ll find that the number of situations in which you want to wear plaid shorts goes way up once you actually have them.

When you think about it, the mysterious popularity of plaid shorts is not so mysterious at all: they’re affordable and comfortable, and while they’re fashionable now, their aesthetic appeal will outlast the trend. The only question is: why don’t you own some plaid shorts already?

Kevin Garnett, Tiger Woods, Eli Manning and Jonathan Papelbon in plaid shorts:

Here is a summary of what has happened in men’s New York clothing trends over the past 60 years.

In 1950, we have 2 extremes, the tidy and the dirty. One young man may be dressed in very formal attire:

Or be playing ball on the street in jeans and white t-shirt:

Then came the 60’s and the revolt from this:

Resulted in this:

The ideas was that you should wear whatever you want as long as you don’t look like everybody else. Which is exactly what happened. Hippies started their own look and many joined in and so started “looking like a hippie.” This involved leather, tie dyed t-shirts, beads, jeans, bell-bottoms, and much else.

1980’s New York clothing was a reflection of much of what was going on during those days. The graffiti “epidemic” was in strong at the time as could be seen on New York City subway cars, and Blondie was popular.

This meant that fashion was an eclectic mix of drab and eccentricity. Subtle, yet ridiculous.

Then came hip-hop and the influences that it brought with it. Baggy jeans galore.
(source: NY Times)

And here we are wearing plaid shorts in the 2000’s.

Full Plaid –
The word plaid itself means blanket, most often a wool cloth with a pattern on it. It comes either from Gaellic (Plaide) or a Scots language. Full Plaid refers to the skirts that accompany traditional highland dress uniform. Its pleats are sewn to keep them from opening. The length of the plaid is twice that of the man wearing it. (Usually only seen on members of pipe bands)
The Kilt –
The most well-known kilt is the Scottish kilt, with its unique design and construction. It is worn at the “natural waist” – above the hip, and below the lowest rib – and has a distinctive tartan pattern (sett), which are individualized for clans and families . Underwear optional. The kilt dates back to the end of the 16th century.

Flannel-
Flannel, which is made from loosely spun yarn (wool or cotton), originated in the Midwest, but similar fabric is traced back to Wales. It was mainly associated with workers in cold climates, such as woodsmen, lumberjack, and farmers.
Then came grunge. Nirvana’s Kurt Cobain (along with much of the grunge scene) made flannel cool again by wearing it on several performances. (photo from www.solarnavigator.net)
Subsequently, West Coast gangster rap began making a fashion statement out of it, making it cool for basically anyone who wanted to wear plaid – as long as it wasn’t tucked into your pants – to do so.

Plaid Shorts –
They became popular around fall 2007, just as the summer season was winding down, and now in preparation of the summer season, any type of summer short can be found in plaid. That includes plaid Bermuda shorts, plaid cargo shorts, and urban plaid shorts. Now even David Beckham can be seen wearing plaid shorts.

Why did they get so cool? Tell us below by commenting on this post!

Take a look at our collection here, starting at just $15:

These are plaid shorts that come in a variety of colors that are perfect for walking in the summer season.