I hope I'm qualified to post on this thread.
Pretty much every drink can have an occasion. Nothing is more manly than drinking a sissy drink with a hot chick knowing that she loves you're confident enough to drink it with her. Wine tastings are a great place to meet women, so I qualify that as manly. But I digress. If you are drinking an appletini by yourself, it may be time for reflection, or you pull it off like a boss and chicks gravitate to you.
As for the Summer Shandy, I'm not a fan. Not because it is a sissy drink, but because there are better summer beers out there. Stiegl Radler comes to mind. If you are into IPA's, summer is a good time. I like to drink a good craft lager like Cigar City Tampa Lager or Sam Adams Boston Lager (or light) in the summer after working outside. Otherwise, summer is a good brown ale season. Don't sleep on the white wines in the summer. Women love a guy who have a basic knowledge of wine. If nothing else, go to Publix and pick up Nobilo Savanough Blanc for about $11. Cheap investment for a pretty decent wine. I good dry Reisling will surprise the **** out of her and earn you some points.
When you are at the beach or somewhere tropical, you have to have at least one umbrella drink. most of them are pretty good. if in doubt or unadventurous, just order a margarita with a good tequila. I could go on and on, but most have already stopped reading this. Drinking is a personal thing on many levels even when you choose to follow others. If you enjoy it, drink it.