What to wear when your Venn Diagram fails you

For some odd reason my professional life routinely comes to a slow-to-screeching halt in the late spring and kicks up again in late summer. During the transition, most of what I do tends to be home-based. While others don crisp summer office wear and hobnob with real live adults, I’m reduced to communicating via phone or keystroke whilst (unwillingly) adorned in never-stylish cat hair and (stupidly) donning clothes that accommodate a little too much snacking.

No offense to people who think the setup sounds like heaven, but: ME NO LIKEY.

So imagine my mega-excitement when an organization recently dangled a life preserver bedazzled with chunks of money in my face. Immediately, I started assembling relevant samples and crafting a presentation and running through answers for some potential “tell me about a time when” queries.

My excitement lasted until I started trying to put together an ensemble that would strike a mellifluous note with the organization’s representatives. Because fiddledeedee, that’s when I:

  • remembered that my recurring bouts of professional seasonitis correlate to an understocked hot temps ahoy! wardrobe
  • realized that my limited number of go-to conservative pieces had (not so) mysteriously become approximately 33.865% tighter
  • recalled that my meeting would involve flying to a very warm, sartorially sharp-yet-relaxed spot for an all-day adventure


Surely after all my quasi-successful efforts in wardrobe management, I couldn’t be in a horrifying Start From Scratch situation, which usually requires a Throw Money at the Problem response?

But I was. And, unless I wanted to risk deep vein thrombosis when airborne and/or post-lunch button malfunctions, I faced both a form AND function challenge.

Clearly, vigorously attacking the former issue before I began my online and in-person shopping would streamline the time-sensitive process. All I had to do was take a look at how it might behoove someone of my age + experience + “position” + personal characteristics to dress when meeting with certain broadly-drawn types during a specific season, right?

After factoring in all the obvious variables, I arrived at the stunningly obvious diagrammatic solution below.

Strategies for First-Impression-Dressing

What to Wear When Your Venn Diagram Suggests You Abandon All Hope

Trying to dress for hoped-for success often takes me to Planet Paradoxical

Note that I didn’t say it was a USEFUL solution.

As I scrambled to assemble options that seemed appropriate—a task made ever more joyful by the fact I was, in fact, often too large for size A and too small-without-dubiously-successful-and/or-astronomically-priced alterations in size B—I resolved to stop reading the angst-inducing Corporette.

Which, given its self-described mission to be a “fashion and lifestyle blog for overachieving chicks,” I have no business reading anyway.

But read I do, since a) in many ways it’s my job to be a voyeur; b) I’m a feminist and appreciate the challenges and triumphs of women seeking lucre and power; and c) the site completely contradicts my mother’s dismissive, now-ancient statement that “No one is looking at your socks.”

However, re-reading discussions on topics like “Skirt Suits vs Pantsuits When Interviewing: Choose Wrong and You’re Doomed,” “Peeptoes in the Courtroom: Empowering or Whorish?” and “Could Feminine Detailing Be Derailing Your Success?”* was starting to give me panic attacks. Obviously I needed to chill, dude.

In the end—and after consulting with a few trusted friends who were roughly familiar with the industry, the area, or both—I went with my patent-pending approach of picking an outfit sure to horrify some and please others.

Winner, Venn Diagram Overlap contest

I hopped the train to hell…er, shinytown…by pairing sedate—and hallelujah lined [thank you for getting your act together, Ann Taylor]—black wool trousers with:

  • a dark grey/faux-sharkskin jacket with a more feminine lapel
  • a sleeveless, ruffled silk charmeuse shell in one of the oft-controversial animal prints
  • my non-subtle vintage shell ring (but hey, at least I skipped the matching bracelet!)
  • my semi-broken in, classic closed-toe and -back shoes in non-classic gleamy pewter
  • that standby of the bless-her-heart brigade: HOSE

To date I’m not quite sure how judgments of my work or appearance** shook out. I DO know that my shiny, 3.5″ pewter heels and I have advanced to the next stage of evaluation…the one where I remember that scrutinizing THEM is a key part of the equation. The stage where I can wear whatever my heart desires, as long as I make sure my nerves are clad in steel.

* Paraphrasing, but not particularly exaggerating

** Having been looking at tons of luscious fall shades lately, I admit I’m a little crushed that I had to purchase more items that will grey my anatomy.