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Crowdsource Activate! Dress an Old.(With pics)

OK, so someone binge-watched some old episodes of What Not To Wear last night, and realized there was a woman that was basically my doppelganger in "style" and "DGAF." I am SERIOUSLY laid back. We live in a tiny rural town. Jeans, jeans, more jeans, usually worn with riding boots in the winter, or my trusty, beloved Minnetonka driving mocs.

Shown here, possibly HUGE. Kinja will decide.

So anyone who's ever watched WNTW ends up thinking about the fab heels and wedges they have in their closet, but never wear, right? I have these (ok Kinja, sure, maybe post this sideways, maybe don't, whatever):


And think I'm liking them with this boyfriend (aka, beloved skinnies that bit the dust) look:

(Um, ignore squalor, I have dogs and a backyard and seriously hate sweeping or swiffering if I know it's going to rain within four or five days. Also image quality, my timer doesn't give you options, it's just 30seconds BAM.) But, I'm thinking the top is maybe too slouchy, and this might need something either more form-fitting, or starchy-crisp.

So.. too "mutton dressed as a lamb" as the old saying goes? Because I'm 44. Like, your mom's age. And while I don't feel old, most days, I am. ish.

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