Never, ever, think about what you’re wearing.

As anyone who knows me knows, my wardrobe is the demon spawn of LL Bean and Eddie Bauer.  The theory behind this is that when I think too hard about how I’m dressed, that’s when things really go wrong.  My solution:  a grown-up Garanimals system in which I can randomly pair the bottom half (denim or khaki) with the top (monochrome cotton) and produce a predictably non-ridiculous outfit.

The problem, as I mentioned, comes when I overthink what I’m wearing.  Examples are as many as they are embarrassing.  Like the time I accidently dressed like the catering staff at my aunt’s fancy Christmas party.  This was an annual event to which our father took us – I’m convinced – because he did not have a date.  I’m primarily convinced of this in retrospect by the total lack of anyone else within 10 years of our ages.  Because of the extreme fanciness of the party and my extreme nerdiness, my outfit was always a great source of stress, til one year I decided that, dammit, I would rock the place, outfitwise.  I had inherited a gorgeous black silk skirt from my grandmother.  Vintage!  Wasn’t that a concept somehow related to hip fashion?  A concept implemented by people who could walk into Goodwill & emerge looking like Katharine Hepburn?  It’s entirely possible that the skirt was in fact cool – I’ll never know because I thought to myself: top?  what goes with a vintage black skirt?  white goes with everything, right?  Now, non-dorks would have put the outfit together and immediately SEEN the problem:  I looked exactly like The Help.  White shirt; black skirt.  I, however, basked in the fashion-free comfort of my logic.  Vintage!  White goes with everything!  Result:  Awkward!

You do NOT want to know what I wore to the first day of my first summer associate job.

By now I’m guessing you’re breathing a sigh of relief on my behalf for the eventual adoption of my Garanimals system.  And you’re realizing that at least half the reason for this blog is a sort of Computer Therapy:  Humiliation?  No! It’s a blog post!

My most recent bout of overthinking was this weekend attending an off-Broadway play in New York.  Everything would have been fine if I’d just worn the outfit selected for and loaned to me by my friend the fashion savvy law professor and her fashion savvy 8-year-old daughter.  I had brought my friend’s dress with me to New York along with the bracelet her daughter had given me from her “jewelry party” – a bracelet that was cooler than 99% of my jewelry drawer.  Alas, it was all back at the hotel when we decided – at dim sum – to simply spend the hours between 2:00 and 7:30 Sunday walking around SoHo.  My cousins assured me that my khaki skirt, Flax shirt, and sandals would be fine for off-Broadway.  Of course I took that advice, right?

Of course not!  I had the genius idea that I could SHOP in SoHo and assemble a cool outfit as the afternoon progressed.

Step one – shoes – was a resounding success.  Sometime in the past few years, I made the decision that I was tired of being short and that there is technology out there – the high heel – to remedy this situation.  I’ve been on a bit of a heel binge ever since.  Happily, we stumbled into a shoe store in SoHo where I bought the coolest shoes I now own:

Cooler still, the store was having a buy one/get one free sale, which forced me to select a lower priced shoe in my size.  Shoes satisfying both criteria were few, so I ended up with something, um, interesting!  And perfect for my next court appearance!

(OK, YOU try photographing your own foot.)

Giddy with my SoHo shopping success, I forged ahead to … hold on.  Context:  It was at least 95 degrees out and dripping with humidity.  So Tim and I were in the process of devoting five hours to walking/rolling, people-watching, walking/rolling, sweating, searching for air conditioned spaces, drinking in air conditioned spaces, walking/rolling, sweating, etc.  It was actually great fun to absorb an afternoon in lower Manhattan like that, but did I mention the humidity?  So when I finally found a dress I liked, I was – what’s the proper word when applied to a lady? – glowing.  Perspiring.  Sweating like a pig.  The dress is actually objectively great, now that I’ve had the chance to try it on in Denver’s dry air.  But I walked out of the shop in a skin-tight silk dress and 4-inch heels, feeling more or less like I was wearing a Zip-Loc bag, and headed straight to the theater.  The humidity was interfering with the complex relationship between the dress and its lining even before we got to the theater and discovered . . . steps.  Five or six of them.  At the front entrance.  At the only entrance.  The nice people in the box office assured me they had a ramp, and so they did.  Tim proceeded up at a 45% slope* with me pushing a bit – in the dress with the lining and the 4-inch heels – into the un-air-conditioned** breeze-free lobby, where we discovered two things:  (1) the air-conditioned theater would not open for half an hour; and (2) the dress code was variations on linen cropped pants (women), cargo shorts (men), and Birkenstocks (both).  I spent about five minutes with my dear husband reassuring me that I really looked “hot” – it now dawns on me he probably meant the temperature and not the compliment – before I went to the ladies room to change back into the khaki skirt.

I couldn’t part with the shoes, though.  I’m not sure a Flax top has ever been paired with 4-inch heels, but I’m sure – logically – that I rocked that look.  Right?

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* Plus or minus conventional building industry tolerances for field conditions.

** How many dashes is that word supposed to have and where are they supposed to go?