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Or, if you live Out West and you’re not in an overtly gay town, you might want to try a cowboy hat. Rule 2: Adult Men Don’t Wear Shorts Once again, I’m not talking about young hipsters and trendy metrosexuals. If you look like the male model (on the left) in the shorts photo, you can wear shorts.I’m talking about guys who are old enough to be totally clueless… Guys who let their mommies dress them, then let their first wives dress them, then let their corporations dress them, then just gave up and put on the easiest, most comfortable things in their closets after there was no one left to dress them. Otherwise, save your short-pants ensembles for times when you are barbecuing in the backyard, hitchhiking along the North Shore, downing mass quantities of beer at NASCAR races, riding your bicycle, hiking the Cascade Trail, and things like that.

A bomber jacket has elastic at the bottom, so bomber jackets are a big no-no for most guys over 40.

This is largely my fault, seeing as I only go out once a fortnight to my local RSL, then proceed to drink the bar dry of Jameson; so I'm not always the most attractive prospect.

Recently, I ran into a charming gentleman by the name of James Maclane, a dating coach who teaches men the essential art of attracting women and was surprised when he rated Sydney one of the best places in the country to go out on the pull. So let's take them one at a time and hear what James has to say.1.

Or, maybe you still work, but you like to let it all hang out on weekends. Yes, there are times when a baseball cap is the right thing for a man over 40, for example, when you’re: The rest of the time, you’re going to look like a little boy who never grew up… And, if you won’t listen to me about losing the cap, promise me you won’t wear that bloody thing backwards.

Either way, I’m here to help you tweak your casual look, babe. All of the ideas in this article are just my opinions. If you want to keep the sun out of your eyes and cover your bald spot, you should consider wearing something groovy like a fedora or an English driving cap. and he’s lucky as hell that I didn’t turn around and walk out.

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