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I had to fight the temptation to wear these shorts with a tighter shirt. Something about them reminds me of my old school uniform, which in fact is not a negative association. Rather, I have since college sought to replace the void left in my life by the absence of enforced kilts, by thick itchy cotton blouses and yes, by stiff ugly navy shorts. These shorts aren't stiff, though they are a little ugly. To offset their bagginess (though I guess if I were truly being complimentary, I'd say "flowiness"), my immediate thought was to go for a tight shirt, but then I was like, "I want to breathe," so I went with the looser one. And you know what? I think it upped the classiness factor by like %100. I mean, if I'd been going full uniform style, I would've worn some cheap Dr. Martins rip-offs like I had back in the eighth grade. But I'm a woman now and and my footwear choices are all mine.