What Not to Wear on your feet

Two seasons of What Not to Wear are on Netflix. Did you know that? I found out a couple of weeks ago, and it turns out that it’s the perfect show to stream for background noise to keep from going totally nuts when you work from home. But, man, does that show have a dark side.

The problem with What Not to Wear is that it makes me want to go shopping in a really bad way. I see all the dressing rooms and the makeovers and I think “Good Lord, everything I own is crap. Please don’t stick me in the 360-mirror room! Pass the trash bin.”

I could use my new job as an excuse to buy new clothes, but the dress code in my new office is basically wear-whatever-the-heck-you-want, so I’m not sure that rationale will fly. (A couple of the gals I interviewed with were wearing shorts. Literally every single piece of leave-the-house clothing I own would be appropriate for this position.)

I could use the new climate as an excuse, but fall/winter looks aren’t out in full force yet. (Trust me, I’ve checked about 100 times.) I dream of sweaters and layering and scarves, but the reality in my casual office, I suspect, will be hoodies and wool socks and parkas. I don’t want to spend money on things that I won’t end up wearing. But there’s one clothing item that I know I can invest in. And that item, my friends, is shoes.

I don’t own a ton of nice flats. I always preferred to wear heels to work, and Sperrys were practically the only shoes I wore on the weekends. But heels are pretty much verboten on the cobblestone sidewalks of Boston. (I see some women wearing them from time to time, but those women are crazy.) I’ll walk/take the T to work every day, so there ain’t no way you’re going to catch me in any shoe over 1/2″ high.

My primary mission recently has been to acquire a pair of nice black flats. Since I’m up to my eyeballs in business casual attire from my current job, I plan to wear those clothes to my new job in addition to some of the more relaxed options. So I need flats that work as well with slacks as they do with jeans as they do with pencil skirts. These are the options I’m mulling:

black_flats_croppedThe Sperrys were my top contender because I couldn’t function without my boat shoes, but I’m worried they’d be too casual for some of my nicer outfits. The Coach shoes are darling, but I tend to gravitate toward tan-on-[color] gear, and I don’t want to get stuck in a rut. The Clarks are funky, but are they Too Much for this simple lady? The Taharis (which are available in black despite what the photo would have you believe) are super me and super cute in photos, but how’s that mesh really gonna look on a human foot? The Ann Marinos are also adorable, but they felt like plastic when I tried them on — a BIG no-no when you have to walk at least two miles per day.

Sigh. I don’t know. Help me, Stacy and Clinton. You’re my only hope.