What are the rules when it comes to wearing button up shirts with shorts and flip flops?

Khaki, white, and grey all work very well as colors for shorts in such a combination, but jean shorts are too casual and black shorts are a bit harsh. As far as shirt colors, you can choose pretty much any color and a pattern as long as it is classic and not too busy or too bright. I would finish it off with a pair of brown leather flip flops. This type of look also works well with polo shirts and boat shoes.

Thanks, Fly. I would never wear black or jean shorts anyway, lol. But what do you mean by “classic” pattern?

Wear the button up shirt open 2 or 3 buttons. (More, if you’re proud of your chest.)

@Sunny2 Yeah, it’s a pet peeve of mine to see other men wearing shirts buttoned all the way up to one button (I’ve even seen a few button them all the way…..Wtf?).

With khaki, you can wear almost anything.

Beach looks are good too… khaki/white/gray shorts with hawaiian shirts and such. Depends on where you live and are going, the possibilities generally are endless. As long as you look put together

@Blackberry Stripes, plaid (preppy plaid, not lumberjack-y), and other simple patterns. Basically, not this.

@Fly Oh darn, now I have to return my shirt that looks like that.

Bright stripes, Madras, or seer-sucker shirts. If you really want to see examples, check out the LL Bean catalog. You’re talking Cape Cod to Maine summer wear.

I would say the silky solid color look good with a pair of cargo shorts and sandals. As far as colors of shirt and shorts you would have to match the 2 colors together like a tan or off white cargo short looks good with say navy blue, or khaki green shirt. Many many other colors go together but these are just some examples. Shirt definately untucked as well looking very casual.

I love khaki and white, or red, or black, actually as was said khaki goes with everything except more khaki.

With regard to flip flops or thongs as they are called here, they are worn with everything. In fact the kiwis have a joke that goes like, how can you tell if it is an aussie’s wedding day? because he has new thongs.

Get the picture.

In addition to the color/style advice you’ve already gotten, make sure you roll up the sleeves, and for casual wear, leave the shirt untucked. If you want to go a little dressier, you can tuck it in and wear a web belt and boat shoes with this look.

If you’re gonna be wearing flip flops, steer clear or the cheap and brightly-colored rubber & plastic kind. Go for brown, grey, or taupe leather or suede ones.

And don’t forget the pedicure.

And don’t lose one flip flop. Australia is littered with single flip flops. I always wonder how drunk you must have to be that you could be walking along, step out of one, not notice it and keep on going! amazing!

I hate flip-flops so my rule would be, don’t wear them with anything!

Just about any colour goes with khaki. Just don’t wear socks, for pete’s sake!

@downtide Oh so very true about the socks, ever so tacky