Hi Steve,
thank you for letting us know. It's weird, because we're testing Skipper on OSX 10.9.5 too (Macbook air) and this is how it looks like:

Can you please check Configuration->Gui Settings->Menu style if you have "Native style" selected?

If so, can you try to change it to Ribbon style, restart app and than change it back?
Regarding problem with attaching images to support site, we will check it.