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.

9 Responses

  1. You looked awesome that day! I’m sure you were plenty shiny enough!

  2. I love the mix of conservative with creative. You owned the shoes already? They’re gorgeous. And hopefully your ring brought you luck, too.
    So glad to know I’m not the only one who does Venn diagrams for issues. I recently did one for career choices and came up with a big gaping empty middle section as well 🙂

  3. Buff —

    Thank you for the pre- and post-support! And yes, for once I was literally shiny but will I have been METAPHORICALLY shiny enough?

    /still scarred from prior hoop-jumping

    Struggler —

    Thank you; I hope I got the mix right. Yes, shoes are a few years old; you liked them when you saw them in an earlier post too, ha. Re my ring: I have to admit it was very calming to stare at while in the airport/plane!

    Glad to find another Venn diagram fiend. Maybe we should start a support group for those who end up in our situation; in honor of Dinesen’s “The Blank Page” we could call it “The Blank Overlap!”

  4. Re shoes: Oh good, I’m glad I’m consistent. 🙂

    Frankly, I’m working hard to fill in my middle blank, but even if that pesky little space does come up white, it still seems like a good exercise to do, regardless of the problem…

  5. Looks very smart. Hope the job went well.

  6. Struggler — Yep to both!

    Ruthie — Thanks! The last few weeks have been very…complicated…in terms of work opportunities, but I’m trying to stay a bit detached til I have more clarity. Tough because I don’t do “detached” well at all, ha.

  7. […] love this post by Building a Colourful Life – how to think about your wardrobe and all the different aspects of your […]

  8. I like the Venn diagram! The partial answered where just 2 circles overlap must help as a stepping stone.

    I’ve recently found myself in a similar spot. I need to overlap looking “business formal” with “suitable for X shape without major alterations” with my natural/casual/bit-creative/bit-classic personality. Suit jacket out of question for the latter two restrictions. Dress – no, not natural/casual enough for me. So I looked for a cardigan with some sheen and decoration, and will wear it with slacks and some gold jewellery.

    – T&S

  9. T&S—

    Yes, the overlap spots did/do help. Funny thing was that I was a bit worried about the “shiny” jacket and arrived to find one of my interviewers in the seemingly matching skirt. So that was an icebreaker.

    Business formal with your style personality must be a tough; I love blazers and silk/drape-y stuff so I’d be good there, but the BF shoes would kill me.

    But if you don’t have to do suits it sounds like interesting, textured cardigans—like the one you found—and artisan jewelry are your best bet. I am not a big wool sheath dress person so I hear you on that, but I think if I were in BF I’d try to see if adding scarves/interesting cardigans might help me love them more just for variety’s sake. Sounds like you and I share a love for softer fabrics….

    When I’m on the corporate side, I’m fortunate in that I generally work in “2nd tier formality” places where one’s in good shape sticking to the middle or upper end of the business part of the business casual spectrum.

    [And as a creative services person I realized being a little more out there was okay/a plus, so I’ve stepped up the colors/prints.]

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