'Sup with the shorts with the inside-part of the pockets poking out the bottoms that I keep seeing on the street? Am I late on this trend, or was it never cool?
What you're describing is better known as Daisy Dukes–and also lately, jorts (jean shorts)–even though Daisy's own pants did not have the pockets hanging out. I think the pocket thing came in a little later thanks to heavy metal chicks having awesome outfits and obscenely short shorts. But basically you make a compromise you with your shorts; you'll turn then into almost underwear but in exchange you will let them keep their pockets and thus, their pant identity. Also, maximum shortness doesn't mean you should give up on the available storage space on your person, so you just let 'em flap out and create weird crescent moon shapes on your upper thighs.
Siwy Jeans Madeline Short $143, Revolve Clothing.
By now Daisy Dukes are a classic summer staple, so in a way they are free of the stigma of being on trend or not; they just are. However, the style has been recently popularized by Hollywood starlets, as their choice of clothing when going to Starbucks and also from the downtown New York City girls who are doing that whole Alexander Wang Lazy-Chic look situation. So feel free to jump in the trend! I'm sure there's a pair or two of jeans in your closet that you will never wear again. A word of advice though: don't turn them into janties (jean panties). Just kidding, I would never use the word janties.
Repaired Floral Denim Cutoffs $178, Rugby.
If you're into the destroyed jeans look, but not entirely convinced about the pockets thing, then these Rugby shorts are a good option. I love that they've made the pocket with a floral fabrics so when it shows through the rips, it almost looks like a patch.
Oh, and yes, of course you can (and should) DIY yourself any and all pairs of cutoff shorts you wear in your lifetime. But that's not gonna bring those advertising dollars in!