Shorts That Aren't Short on Style

It's summer and it's disgustingly hot right now (at least where I am) and dressier looks are rarely light and cool.  Every guy is familiar with shorts and most guys owns a pair of shorts (I say most because it seems a small number of guys won't touch them), but shorts are typically casual and worn as such.  Now just because shorts are not business casual attire, doesn't mean you can't dress decently with them and make them look mature and classic.

Unis Spring/Summer 2010

First, we will start with the shorts themselves.  As mentioned in a previous post, the trend this summer is a nice tailored fitting pair of shorts, not too long and not too short.  Tailored doesn't mean tight, just fitted (if you want to rock converted skinny jeans and a vintage concert t-shirt, go for it, but this post is about dressing them up).  As for style, play with color and various stripes and patterns.  It can all work well if you can match it to the rest of your outfit.  My only recommendation is avoid those patterned Polo logo shorts.  The walking billboard is already a bad look, don't get ridiculous.

Unis S/S 2010... again.  It's a great collection.

Next, we are going to work our way down.  Shoes are going to be vital to tying together your outfit.  Shoes will also be a key component to dressing the style up.  Loafers are a great option to class up shorts and is a look I have been sporting often this summer.  Just wear them without socks.  Worn in and vintage loafers will have a nice casual and comfortable look while dressier loafers will class it up more.  Canvas sneakers are another great option.  You can find them in a number of colors that will spice up a look, or stick with the classic white that will always work on those hot and sunny days.  You can even pull off dress shoes if you want to go for a more fashion forward and edgy look, just be careful.  There is a fine line between fashionable and foolish and the 'dress shoes with shorts' look dances around it.  And last but not least, boat shoes as always are an obvious choice, but we are here to try something new right?

Dress shoes and shorts done right.  

Next up is the shirt.  The simplest way to create a classic look is to go with a short sleeve collared shirt.  You can vary up the colors and patterns on this one, just make sure it goes with the shorts.  Avoid mixing patterns as it will clash the vast majority of the time.  A good rule is if you have patterns or stripes on your shorts, go with a solid color shirt and vice versa.  You can also try out a tie or bow tie with a dress shirt.  It won't be as dressy as a long sleeve shirt, but it will be a fun look and make you stand out.  Another option for those days where it's not unbearably hot is a sweater or sweatshirt.  A classic dressed down and comfortable look is the grey basic sweatshirt with shorts.  Sweaters can work, just make sure they are very light weight.  You don't want to bring out your ten pound knit wool sweater in July.

Striped Sailor Pullover - American Apparel - $40 

(I have this in grey/navy stripes and it looks great)

Finally, we have the accessories.  Refer to my previous posts regarding sunglasses and jewelry.  Hats are always a good summer accessory for their practicality.  Fedoras can work well with these summer looks if they work well with you (I can't pull of hats for my life).  Just keep the baseball caps in the closet.  I don't think anyone will see a baseball cap as a good addition to an outfit.


This is just a basic guide to work around for creating a classic summer look with shorts.  Is there a particular look with shorts that you like or do you have any other tips to share?  Leave a comment!