A tougher-than-anticipated task

I just purchased a pair of boots -- they look like these (see below), and I was wondering what I can wear them with. They were at at a vintage store here in West Virginia so I didn't want to pass them up because they were so comfortable for a heel, but now that I have them home I can't bring my self to wear them out of the house. I don't plan on wearing them to work or anything, but on a weekend how can I make them work?

Before I begin, I want to thank this reader for her kind patience; she submitted this question to me over a month ago, and unfortunately, due to my utter lack of organizational skills when it comes to e-mail - or anything non-work or non-outfit related, rather - I'm only just now addressing it.

Apologies out of the way, I'm going to be frank with you, M, I'm not a big fan of the half-pump, half-bootie (in fact, from here on out, I reserve the right to refer to this shoe as a "pootie"), whether it be suede, patent, or matte leather, vintage, couture or a mid-priced knockoff. For the same reason I recoil at the sight of wedges, espadrilles and most stacked heels, I simply can't accept into my own wardrobe a shoe that, in my view, makes a woman's foot look indelicate.

I know, I know, the contrast of a larger shoe to a thinner ankle and calf might even enhance the appearance of delicacy, but in most cases, when the woman's legs don't have a Pick-up-Stix quality to them (think Olsen-twin thin) and fail to exhibit even a hint of muscle definition, this kind of shoe - one that hides the all-important calf-to-ankle contour - will leave her feeling stocky rather than stylish.

But if you love 'em, you've got the legs for 'em, and as you've indicated, you have the good sense not to wear them into the office, who am I to try to discourage you from indulging in what is still clearly, as evidenced by their presence on every catwalk from Milan to Paris to L.A. this past season, a very in vogue footwear choice for Fall?

As for suggestions, the most palatable "pootie" pairings I've seen in-person both in New York City and along the U Street corridor here in DC have been those that integrate this unique shoe into the "theme" of the clothing that surrounds it. In other words, funkier, trendier, riskier looks that are by no means limited to but might include a pair of colored skinny jeans, a super short mod mini, or an exaggeratedly high-waisted skirt with a cropped leather bomber -- something that without question sets an edgy tone.

What you don't want to do is what I refer to as "Carmen Electra-ification" which is to either try and get away with wearing a highly-trendy piece with an otherwise pedestrian outfit or the eponymous offender's more frequent inclination to throw every every single one of Vogue's "Top 10 Trends for Fall" into a singular ensemble. This means no pairing the "pootie" with bootleg jeans and a from-The-Limited cami OR throwing it into an outfit that includes a funnel-necked mini, a swing jacket with rosette detailing, leather driving gloves, an oversized fringed bag and a large pair of bushy, run-wild eyebrows.

As with anything (other than relationship drama, of course), healthy moderation is the key.

M, I apologize in advance if this wasn't as helpful a response as you were expecting, but I hope you'll again demonstrate patience with me and try to understand that the notion of accepting tastes that run contrary to my own and trying to build recommendations around them are both very much foreign concepts. Baby steps.