to chuck or not to chuck?

This year I bought two pairs of Chucks. One for my little sister and one for my little niece. Nada for me. The thing is, I've always been intimidated by Chucks. I know that sounds ridiculous, but for a tiny 28-year-old person, it really is. The line between insouciant cool and adolescent playing dress-up is a fine one when you're 28 and barely 5 feet tall.

Do you think it can be done? Do these J. Crew looks only work because these chicks are super leggy and skinny? Or do small chicks with hips have a chance?

Will be pondering this issue until I see a small chick my age successfully rocking Chucks. And then I might actually shell out $65 for J. Crew's Jack Purcell sneaks. Maybe.

to otb or not to otb?

Dear readers, I am treading dangerous waters ... I thought I would be immune from desiring over-the-knee boots because I'm usually more practical with shoe buys, but these gorgeous Dolce Vita "Eve" OTBs are seriously testing my resolve ...

It's that beautiful buttery looking leather on the left that is whispering sweet nothings in my ear, although if I go for it I'll probably end up buying the black ones. I've been daydreaming of prancing around in minidresses, opaque tights and OTBs for the next few months, and these are the perfect mix of sexy and sleek. I love that it's flat and completely unadorned, just all nice lines and good leather. OTBs run the risk of giving one a "working girl look" but these are far from that. They cost $295 at Bloomingdale's, which is not a bad price to pay. I know that the trend will not last, but so far my boots have always had a lifespan of 2 years because of all the walking we do in Manhattan, so if these boots are out in a year or two, it's not tragic.

Am I trying to convince you guys or myself? Hmm.

Would you OTB?