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.

Gratuitous Color Shot #4: Horton in the house

Lately my time has been occupied with a mix of superficial + potentially life-course-altering tasks, tasks which are helping to distract me from simmering extended-family issues over which I have approximately zero control.

Of course by “distract” I mean “tip my stress management meter reading from ‘Handling’ to ‘Expressing Overload Via Bizarre Minor Health Situations That Generate Eyerolls.'”

I swear I’m putting a lot of effort into stepping back, but really: what’s the protocol when the proverbial elephant moseys into one’s living room and can’t get everyone’s full attention? Besides hope the the elephant is pink, and thus an accepted marker of drunken hallucination.

[Except when it’s an even more tangible sign of HEY, OVER HERE!]

Hallucinating BIG pink elephants or crossing paths with Seattle signage?


Though the rosy-colored variety gets a bad rap in Western culture, bog-standard elephants represent many wonderful things in their native lands: faithfulness, intelligence, strength, wisdom, endurance, memory, prosperity, sexual vigor….

All those enviable qualities certainly come in a large, hard-to-miss package, though. Maybe those of us who are waiting not-so-patiently for others to see the room is rather crowded need to take a deep breath—or twelve—and throw tons of effort into channeling the metaphorical guest.

Salad, anyone?

More Emily Dickinson than PT Barnum

In the late 90s, I accidentally scratched out a bedtime story that seemed to delight more than a few children and a surprising number of insomniacs. A few years later, a friend called in a favor and made an offer: if I wanted, I could get free spec illustrations from a local artist.

I wanted. And after meeting with the illustrator, I received his designs, designs that embodied the untamed energy I had tried to portray. He deftly added so much heart to my text that 10 years later, his images continue to melt mine:

But as I was neither That Kind of Writer nor ambitious, I shopped the story half-assedly. Eventually I shopped it again—still half-assedly. Had I done it more throughly, I’m pretty sure the additional rejections would have put me well over my oh-we-really-we-don’t-want-to-go-there RDA. [No wonder Those Kinds of Writers tend towards depression and go gaga for groupies!]

Overall, the process seemed very unseemly, with more than a whiff of S&M, for a storybook. Of course overall I probably seem very unseemly, with more than a whiff of S&M, for a storybook writer.

Occasionally, I’d rouse myself and think, “Why don’t I try going around vs through the industry’s hoops?!!” but I didn’t exactly put any effort into doing that. More specifically, I put NO effort into doing that. Unless one counts daydreaming about emailing my little creation—“Eloise meets Good Night Moon!”—to the staff of Oprah or Katie C. Though perhaps I can get points for doing a little light scheming about partnering with a mattress company.


But I did nothing. Why? With literally nothing to lose, why I couldn’t bring myself to do something mildly zany? Ridiculous. Or way f’d up.

So now I’m going to post it on the internet.

Ridiculous? Or way f’d up? More a reminder to myself that external validation doesn’t set us free from internal demons. Sure, it’s easier to endure a life that’s more pats-on-the-back than pokes-in-the-eye; I’ll trade this pirate patch for a sore vertebrae any old day.

But I’m beginning to believe that if we don’t make the space for our happy endings, they’ll go elsewhere. So I’m tossing out a lot of mental crap, sweeping the hippocampus, playing Barry White to my anterior cingulate. After all, I’ve got nothing to lose by trying to lure in a happy ending or two…and everything to gain.