I agree with Jamison. The shorts aren't working for you. However, as a cyclist, I needed to find something that would work and I found that loose fit cargo shorts work for me, you may just have to shop around a bit. There definitely is something about plaid that doesn't work I've found. I only own one pair of plaid shorts and it's more a hidden plaid, they look black until you get close up. Lol. I do own some plaid shirts despite the "rules" but then again, I'm in Canada, home of the lumberjacks, and many guys have plaid shirts so that's fine. But plaid shorts, no. They're rare outside of the hipster crowd.
Female thighs tend to have this thing where they're always in contact with each other just because of fat distribution in this area. Women's shorts work for that fat distribution to sit right, but men's shorts tend to sit badly on female fat distributed hips and thighs and cause this weird thing where they point inwards after the hips which is what I can see happening in this pic with the centre at the crotch sitting funny and the inside lines of the plaid being higher than outside. You get away with a lot more in pants but shorts are definitely a tough one with female fat distribution. Some get lucky, but for the most part, nope
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The hat thing I agree with too. The hat says hip hop and then you get to a pistols tee and think, "WTF?" but that's more style than passibility, although avoiding second looks always helps lol.
