When you find yourself snipping the frayed, gnarled rubber off the heel of your fave shoes – as I did last night before donning my Aldo triple-buckle, biker chick-esque, ankle boots – it’s time for a new pair. I don’t care about the hours you spent breaking them in, I don’t care that from far away, they still look alright – this isn’t an effing Monet we’re talking about. The only thing worse than a cheap pair of shoes is a decent pair worn past their expiration date. We don’t need to cling to those haikus markered onto our nine-year-old Converse sneakers; this isn’t Cheap Hipster, people.

As my ankle boots have officially crossed the line from broken-in to busted, I’m on the hunt for a new pair. Here’s what I’m thinking so far:

I get an overwhelmingly icky feeling in my tummy when I pay more than $150 for a pair of shoes. It’s probs the same feeling the shoe-obsessed get when they pony up for a handbag. So the Dolce Vita Zip Belted Bootie, at $213 is slightly out of my reach. Not that it can’t be tracked down at Loehmann’s or Century 21 for far less – I’ll be keeping my eyes peeled. The We Who See Rise Bootie, is reasonably priced at $78. Alas, it’s canvas and I need these puppies to see me through the gray, icey street sludge all winter. They’re a maybe.

These Frye “Andrea” Mid Boots ($348) are so well-made that it almost makes them worth their heinous pricetag. I know this because I inherited some Frye boots from my mother and – after five years – they’re still kickin’. Meh. The
Naughty Monkey Out Cast Booties, ($80) are either really weird, or really cool. Or maybe weird is cool, oh I’m sooooo deep today.