OUTDOOR HEADSHOTS + PHOTOGRAPHING MEN

Often times when we sit down and think about headshots or single people (one, not as in your relationship status) we assume that it needs to be inside the studio and it needs to be your nothing special head shot on a black or gray backdrop and in a suit or tie.  Not everyone needs that. If you own a construction company and want to market to your local industry and bring it to a home owner level you really don't want or frankly need an indoor headshot.  Look appealing to the customers that you're trying to reach.  Be transparent.  Be open to an outdoor headshot session and be open to incorporating something besides just yourself.  Possibly your family, your favorite pet to be in the photograph, something that will stand out and express who you are and what you're bringing to the table.
I'm a photographer, but honestly, you wont see me with a camera in my hand in every shot and I am most definitely going to be showing off my family.  I'm  a family photographer, why wouldn't I want my family to be photographed and to show you images of them right?  I mean... who best to photograph YOUR FAMILY than someone who has a family.  You probably don't want random Joe who doesn't like kids and photographs real estate or weddings to be photographing your family if your photographer doesn't have that special connection with kids. 
As a photographer I very much have been given a passion.  I love the art of the "moment".  I love to run around frantically trying to shoot children and let them be in their element of happiness.  For every image that I get, I've probably let that child run around for 3 to 5 minutes between just trying to hard to get that energy out so that when I need them, they stay connected and are ready to please mom and dad and of course me (your photographer) because they aren't constantly getting the "look here Joey, smile!".  You really have to be engaging. 
Now back to the subject of getting those headshots outdoors.  Bring multiple outfits.  Bring a casual one, bring a nice pair of dress shoes and a shirt.  Don't bring one outfit whether or not you're a girl, guy or a group of people.  You want the images to look like you so be you, but be a well dressed you.