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See the look on his face? That's the look of a man who knows his suit fits him perfectly. The jacket's shoulders hug his own, the waist isn't too tight or too loose, and the pants just brush the top of his shoes. This guy should live in tailoring.

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Navy blue will never do you wrong. You can mix multiple shades without worry, since they all go together. Plus, it's flattering on every guy. Oh, and it's a nice counterpoint to a pair of medium-gray chukkas, as Tom Hiddleston demonstrates here.

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That is not how you do pants, Joakim Noah. That is not how anybody should do pants.

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And that is not how you do Chelsea boots, Jesse Metcalfe. While it sometimes—sometimes!—works to stack skinnier jeans on top of chunkier boots, the Chelsea's streamlined silhouette demands that you let your hems fall all the way to your actual ankle, not just the top of the boot.

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We already know that Eddie Redmayne is very good at wearing a suit. Here, he shows us the right way to make a classic chore jacket feel current—by blending in a bit of whimsy (the sweater) and a bit of polish (the shirt).

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The over-processed jeans. The too-long jacket sleeves and too-deep unbuttoning of the shirt. That mustache. In this getup, with that facial hair, Colin Farrell looks like the kind of guy who has "connections" at the seediest club in the city, and isn't afraid to brag about them.

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John Legend, on the other hand, looks like a cool dad that hasn't completely abandoned his youthfulness, thanks to one very good varsity-inspired jacket and a range of well-chosen supporting pieces.

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Look past the tee and whatever is hanging from his waist. Look to the shoes, and see that they are of two different sorts—one being Pharrell's impossible-to-get "Friends and Family" NMD, the other an Ultra Boost, both by Adidas. If you're asking yourself, Is wearing two different shoes at the same time some sort of thing now? the answer is no. No it isn't.

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The guy looks good! All due credit to a great leather bomber. But he could look better if his sweater were long enough to actually cover the bottom of his shirt. If you're tall like O'Brien, this is something to watch out for.

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The athleisure thing is starting to feel pretty played out, but Joe Jonas executes it well here by 1) going full monochrome, and 2) bringing in just a bit of texture with the stripes on the Adidas tracksuit and the woven uppers of his Nike Air Prestos.

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