I’ve been searching for the perfect pair of black booties for what seems like eons now. I’d love a walk-able heel (I live in Toronto and walk a ton) but nothing dowdy. I’m a university student who wears an awful lot of ’50s-style dresses and red lipstick, but I do have a pair of spiked 5-inch heels that I break out for parties on the weekends. Can you suggest a boot? — Colleen

Manolo says, ayyyy! To think it is now 2012 and we are living in the future, which, strangely seems not all the different from the past, except that all of our best friends live in something called “cyberspace” and all the teenagers communicate entirely with their thumbs.

But otherwise, everything seems familiar, as we still live in houses made of wood and brick (instead of moon rocks and plastic), and the Rolling Stones are still the touring band (although Mick Jagger now looks like the folk-art dried apple doll).

Happily, despite this being the future, many smart young women wear beautiful vintage clothing in inventive and stylish ways and thus require shoes that enhance such creations without seeming too costumey.

For the example, pairing the 1950s dress with the 2010s booties, the practice which has much to recommend it.

Here is the Chaps from the Elizabeth and James ($280, Zappos), the stacked-heel bootie which would complement the full skirts in the most non-dowdy manner possible.