What is it about stylish people traveling in packs? These two really caught my eye—and dragged it 50 feet.

She's wearing black on black on, well, black—always safe, always in style, always elegant. Don't let the Pollyanas of the world tell you otherwise. Yohji Yamamoto's Y-3 and Commes des Garons have done this for years now, and why? Because it still works. Clean lines, solid-colored pieces: it's all so refreshing to see, especially after this past fall's layered hobo explosion. (Of layered hobos.) Don't get me wrong, layers are still good—just not the hyperbolic Mary-Kate-2005 layers. Those make me sad.

Keep it simple with tapered black trousers, peep-toe heels, turtleneck, a cropped-tie cardigan and a wide-brim floppy hat (popularized by Jennifer Lopez). Like our gal here; her outfit repeats a subtle bow-tie theme: the hat, the cardigan, the shoes. I like!

Now, the guy. Yeah, he's “just” wearing a terry gray hoodie, T-shirt, jeans and sneaks, but it's that whole urban Japanese street fashion thing that's so popular these days. Just look at Pharrell Williams and countless other hip-hop artists who have left the days of silk Versace handkerchief button-ups and jeans-six-sizes-too-large long behind them. Let's examine his hoodie (the guy's), and the phenom of the designer hooded sweatshirt.

The trend revolves around its Japanese golden calf: A Bathing Ape, or BAPE for short. Started by the now infamous Nigo in 1999, BAPE doesn't really go beyond the essentials of T-shirts, hoodies, colorful sneakers and printed hoodies that are multihued enough to send you into an epileptic fit. An obscenely high price tag and hard-to-find stores (usually unmarked! And all overseas!) helped skyrocket the line. The label's been on the scene for some years now, but when I started seeing head-to-toe BAPE on everyone from the Madden brothers to Steve Aoki, I decided it was enough.

But! Our guy here has taken that look down a few notches, with a hoodie featuring an understated bleach pattern and line design. His large owl belt buckle, sunglasses-at-night and gray sneakers with a few specks of teal, blue and purple really let us know he knows what he's doing. Or that he thinks he does. We believe him.

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