Straddling function and fashion, leisurewear finally puts its foot down

You may confuse the Nike Woodside with the classic L.L. Bean duck boot. Both boast a rubber sole, a synthetic midsole, and a leather upper. The Bean boot is hand-made in Maine, and it is waterproof and functional. The Woodsides are none of these things, but you should consider Nike's Frankenstein farm-meets-downtown anyway, since they are slick and go well with jeans. ($110, Undefeated) - J.M.

One of my uncles is an avid tennis player and refused to play in anything but the
Adidas Stan Smiths. We used to have to hunt them down for him anytime we visited the States, a proposition that became progressively more difficult when the shoe faded from the market. The Stan Smiths are back, and they're just as wonderful as ever: elegant, low-key and comfortable. Wear the hell out of them. Call my uncle and see if he's up for tennis - he probably is. ($64, Undefeated) - J.M.

Chuck Taylors have had more high-end design collaborators than you'd think necessary for what is, in essence, an obsolete canvas-and-rubber basketball shoe. No redesign is really necessary. The shoes are pretty wonderful on their own. That said, why not go for these Comme Des Garcons? They got little hearts with eyes on them! I'm pretty sure they're for girls! Who cares? ($100, Undefeated) - J.M.

Should you want to stick with classics, you're better off considering the Prada suede chukka boot - perfect with khakis or jeans or even shorts in any outdoorsy activity, including picnics, Desert Springs outings, and (I'm guessing) light-to-moderate warfare. ($495, Neiman Marcus) - J.M.

It's time to face it: TOMS are cool. If you overlook the rather awkward construction, you can't resist the we're-all-in-this together, feeling-good about-the-charity aspect of the whole business. Let's be self-congratulatory in silver glitter! ($54, Suite 160)  - S.N.

Fact one: Flats can be an awfully lazy choice. Fact two: A touch of velvet makes almost anything look dressed up. Turn to these Prada Bordeaux Velvet Sneakers to rescue a basic jeans and T-shirt combo and keep the Fashion Police off your case. ($295, Neiman Marcus) - Sara Nunn

Tied up with ribbons and chicer than chic: This is how the Parisians of our imaginations wear sneakers when they're not click-clacking in stilettos down the Champs-Elysees. The Lanvin Snakeskin Print Sneaker even provides the slither for you. ($495, Neiman Marcus) - S.N.

This shade of red paired with this UNDFTD x Vans Hernan Era LX Preschool Sneaker brings to mind only this: that it;ll look exceedingly find as the last thing someone sees before getting kicked right in the face.  Not that we advocate violence, but if we did we only hope it would be so stylishly delivered. ($40, Undeeated) - S.N.