Sidewalk Style: He Says, She Says

He Says: I love all the colors in this outfit, and a fedora on a woman is always cool in my book. I'm not sure what's going on with the sheer skirt, but I'm pretty sure she's wearing the key to my heart. She Says: A little over-the-top color-blocking never hurt anyone, and she's definitely doing it the right way by sticking to clean lines. I love how the retro shoe is playing peekaboo from underneath the sheer aubergine skirt.

He Says: Cool sunglasses. The snakeskin bag is sleek and sexy, but I could do without the skirt.She Says: Windowpane plaid is perfect for fall, especially when paired with suede Mary Jane heels. I love the oversized clutch in a pop-of-color snakeskin. And the cat-eye sunglasses? Yes, please!

He Says: This is a tad aggressive. From my perspective, pick one printed piece.She Says: She is a little camouflaged with the foliage, but mixed prints are a great way to make a bold statement, especially when they're all in shades of black and white.

He Says: I like that she's showing some leg with a short black dress and dressing it up with classic pearls. She Says: Refined goth = amazing. Adding a floor-length coat over a shorter dress makes this LBD cool-weather appropriate, and topping off with a floppy felt hat adds an unexpected super-chic element.

He Says: I don't understand the socks-with-the-heels look. But I do think her outfit looks like she raided her brother's closet and made the preppy look cool.She Says: Trompe l'oeil is the name of the game for this edgy spin on the Peter Pan collar. The overall combo of the collarless blazer, red shorts and, yes, socks makes for a cheeky co-ed look.

He Says: I'm not a fan of the dark lipstick, but I like the lacey top with the long black skirt. She Says: This is a daring look, especially with the one-shouldered jacket, but she pulls it off. The feminine lace tank plays well off the sleek metallic collar necklace.

He Says: I get that it's in to be edgy and wear gender-bending clothes, but I think this is a little much.She Says: What's more fun that wearing a boy-meets-girl outfit while traipsing around town? When going androgynous, try a clean-lined silky blouse for a feminine touch.

He Says: I need sunglasses to look directly at this.She Says: She is definitely embracing the neon trend, but try pairing mega-watt hues with neutrals for a more wearable look.

He Says: I love the grown-up schoolgirl look, and the brown carryall adds a little warmth, instead of typical black.She Says: It's a very sweet and playful look. Wearing knee-high socks with a short skirt is a demure way to cover up.

He Says: She looks comfortable, and you could wear this dress anywhere. I like the burnt orange color and simple floral print. She Says: Forties fashion done right! The delicate print works well on her petite frame, and the below-the-knee length paired with a peep-toe is a flattering length for almost anyone.

He Says: This outfit is sexy in an elegant way.She Says: I'm in love with this pleated, floor-sweeping maxi! Paired with a lace blouse and quilted clutch, it's oh-so chic.