Summer School: Grading Celebrity Style

Progress Report: Leonardo DiCaprio makes a case for the slip-on sneaker. His predilection for washed denim suits him well, especially in the warmer months. He also isn't afraid to take style risks, like tying his jacket around his waist.

Needs Improvement: DiCaprio should lose the newsboy cap as soon as possible. There are also far better ways to go incognito rather than constantly pulling hoods over your head. Life isn't Assassin's Creed.

Progress Report: Miguel is treading on that "edgy, well-dressed crooner" category in the vein of guys like Dave 1 from Chromeo. The black Chelsea boots, skinny black jeans and trousers, and his well-coiffed hairdo are fast becoming style signatures, In warmer weather, he switches it up with blank tanks and sleeveless motorcycle vests, which he actually wears well.

Needs Improvement: Miguel tries to mix tailored clothing like tuxedos with casual gear like T-shirts, but it wouldn't hurt him to go fully formal. A skinny suit would look really great on him.

Progress Report: Justin Bieber has gone off the deep end. From horrendous drop-crotch pants to ill-fitting shorts that practically touch his ankles, his style has taken a turn for the worse. To be honest, we don't even know if he's trying anymore.

Needs Improvement: The leather baseball jersey shows potential, but Bieber needs to exercise the art of restraint. Once he learns how to balance out loud pieces with more conservative looks, he could definitely look so much better.

Progress Report: For a while it looked like Scott Disick had completely adopted Kanye West's penchant for leather goods and sneakers. It looks like he's managed to find a happy medium of his previous tailored, European look with a little bit of a streetwear vibe. That's ideal for warmer weather, and we like how he makes a case for solid long sleeve T-shirts and a crisp pair of washed denim. He pulls off cotton navy and bright orange chinos like a pro by balancing them out with complementary colors.

Needs Improvement: Disick needs to ditch the driving shoes and ill-fitting polo shirts to avoid the typical "rich douchebag look." His jeans look best when they're slim and tapered, so he shouldn't wear more forgiving straight leg fits, they make him look like a herb.

Progress Report: Rocky's style is really consistent. He stays within the black-and-white color palette, but doesn't do it in a boring way. He plays with layers really well, like throwing leggings under basketball shorts or pulling up the legs on a pair of sweatpants. It's not all predictable brands like Hood By Air and Pyrex Vision either-he recently busted out an old Supreme T-shirt from their collaboration with Neighborhood.

Needs Improvement: Sooner or later, Rocky's gonna have to switch up his style to keep himself in the conversation. But we have no doubt the Harlem rapper will have no problem flipping the script on us.

Progress Report: With a little scruff on his face and a nice pair of glasses, Steve Carrell goes from "fuddy-duddy" to "attractive dad." The funnyman's casual vibe is getting better too. In addition to wearing a pair of aviator shades that really suit his frame, his kicks are on point. He wears understated sneakers really well, and pairing New Balance 993s with washed denim is a tried-and-true "cool dad" maneuver that works for him.

Needs Improvement: Carrell needs to find a reliable tailor to help him take his suit game to the next level. He looks like a guy who's buying everything one size too big. Slimming the fit of his gear down just a tad would do wonders for his overall style.

Progress Report: Jay-Z's style is inconsistent. It's hit-and-miss, but even the "hits" aren't as good as they could be. His black-and-white attire looks good sometimes-like when he opts to accessorized a leather paneled coat with gold, Timbs, and a Don C. snapback.

Needs Improvement: Jay-Z needs to buy some new shorts. The leaf-print ones were cool, but the plaid ones he wore to Cuba need to go. Coordinating them with a fedora and turquoise polo was a poor choice too, and while Nike high tops are cool, they don't mesh with the whole "I'm on vacation" vibe.

Progress Report: Kendrick Lamar seems to have an excellent grasp for what works for his body type. He really runs the gamut, from custom sweatsuits to Hood By Air leather pants and shirts. When he goes back to basics, he does it well: slim white tees, simple caps, washed jeans, and a mean white sneaker game.

Needs Improvement: None needed. Lamar just needs to keep his game consistent.

Progress Report: Examining Kanye's style is like grading the advanced courses. That said, he's pared back his wardrobe considerably, eschewing a lot of recognizable designer pieces for minimal gear. Lately he's shown a dedication to black leather pants and exaggerated proportions like oversized hoodies and military jackets. However, we can't get behind the coordinating leather shirt and pants. That's just OD.

Needs Improvement: If West wants to really embrace a minimal look, he's going to need to stop with pops of color like the red Yeezy IIs, and consider fabrics that are a lot less flashy than leather. A well-cut garment made from cotton will suit him more than a loose-fitting leather shirt.

Progress Report: Drake has stepped up his game considerably. Besides rocking brands like Hood By Air, he pulls off designer gear from Dries Van Noten, and even looks good in baseball-inspired button-down shirts.

Needs Improvement: Drake needs to upgrade his resort steez. Black tank tops and Jordan ball shorts might be fine courtside, but they won't leave you smelling like a vacation.