Asking the Right Questions

Being properly dressed (or, if we are striving, well-dressed), requires a little bit of planning each day. A surprisingly small amount. For me, every work day starts the night before with three questions, asked in rapid succession: What should I wear to work tomorrow? What can I wear to work tomorrow? What am I wearing to work tomorrow?

What do you think I should wear to work tomorrow?
What should I wear to work tomorrow, Giant Head?

When I ask, “What should I wear to work tomorrow?” I am quickly consulting my calendar to see what appointments I have. If I am meeting a client, getting a haircut, or going out after work (fundraiser, bookclub or ballgame), I will dress differently to accommodate the particular requirements (or comforts) of those plans. I also check the weather.

When I ask, “What can I wear?” I am checking to make sure that whatever I’ve started to visualize is clean, pressed, and in good order (no loose buttons or tentative hems).

By the time I get to the last question, I’ve whittled things down quite a bit and so the deciding factors are: (a) whether I’ve worn something in the last 7 days and (b) what I feel like wearing.

I’ve broken this down like an industrial engineer, but in practice, it take me less than 5 minutes to pick something out. It might take less than 3 minutes. But I have noticed that if I wait until morning to pick out my work clothes, the decision is much less efficient — and sometimes the whole process goes completely sideways (frantic donning and doffing of outfits), which causes me to start the day late and cross.

Note: A more sophisticated planner — the Sakadagami (if I may borrow the Buddhist taxonomy for this most material discussion) — looks at her calendar for the whole week and takes note of any important meetings or events, and then checks the bulletin board to make sure that nothing she’d like to wear is at the drycleaner. The fully enlightened — the Arahant — is working on a fortnight time-scale.

4 thoughts on “Asking the Right Questions”

  1. I also pick out what I’m going to wear the night before a work day. I hate making what-to-wear decisions when the alarm goes off and I’m half awake!

  2. Do you ever suffer from the tyranny of choice? Analysis paralysis? I think this is why so many people (like me) want some hard-and-fast rules for dressing. It’s the part b, above: what I feel like wearing. Often the answer would simply be “sweatpants.”

    • I do sometimes — I find it harder to pick something to wear when I am under time pressure. My question for you is: Why do you feel like wearing sweatpants? Because the answer to that question might help in laying down some hard and fast rules for you. If, for example, you like the easy fit of sweatpants, you might want to look for dresses that skim the body, but are not tightly fitted anywhere. If you like sweatpants because they are soft and cozy, you may need more knits in your closet. If you reach for sweatpants because you know where they are and how they will look, you might be able to find the same certainty by planning three or four go-to outfits with the help of a friend at the start of each season.


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