Why I Wear What I Wear When I Wear It

Reader Question: 3/17/11

Yesterday, the lovely Sue asked me: “How do you decide what to wear each day? Do you plan outfits in advance (besides for things like Everybody, Everywear)?”


A section of my very messy closet.

First things first, I am not a planner. As is evidenced by the shot of my closet above, I am not the most organized person (color coding aside).  And although I do try to jot down outfit ideas in my journal, I rarely plan a specific outfit for a specific day.  Yesterday’s outfit wasn’t anything I have even considered before and I just got lucky with how well it turned it.

Even though I don’t plan my outfits, I do have some questions I ask myself that help me decide not only what to wear to work, but to wear anywhere.  For me, it all comes down to two questions.  Who am I?  And what am I doing?  I start with these two questions and any follow up questions to help me determine what to wear.

I usually address the second question first.  What am I doing?  Or, alternatively, where am I going?  For example, let’s say I’m going to work. 

Where do I work?  I work for a state agency, in a cubicle and I am never public facing. 

What is the dress code? My work environment is very casual with only a few of us, if any, having any interaction with the public except for over the phone.  That means people wear whatever they want.  From sweats and flip flops (no really) to sequined skirts and four inch heels (again, really).  Those are extreme examples, and more of my co-workers dress casually, in jeans (and Christmas sweatshirts in July), than wear sequins and heels. 

How do I get there? On top of a casual work environment, I ride my bike to work all year round which means I often have to contend with the Oregon rain, and sometimes even snow.

My answers to the above questions might indicate an extremely casual work wardrobe would be in order, but that’s where the second question comes into play.

Who am I?  I am a lover of bright colors, sequins, blue shoes, feather earrings, scarves and thrifted clothes.  I don’t like feeling confined by my clothes.  And I firmly believe in dressing for the occasion with the caveat that I dress to my standard of what’s appropriate for the occasion.  And most importantly, I wear what I like – I don’t insist on fitting in, but I don’t wear anything that makes me stand out uncomfortably either.

So how does all of this affect my work attire?  Although I do wear jeans to work, I won’t wear sweats or workout clothes.  Ever.  I am also someone who likes wearing skirts and dresses.  So, even though I do ride my bike to work, sometimes in inclement weather, I often wear skirts and dresses.  I am not someone who likes being cold though, so I wear dresses less during the winter or I wear lots of layers.

Even though I am not someone who insists on fitting in, I’m not comfortable sticking out like a sore thumb, either.  At my height, I can’t help but draw attention to myself, but that doesn’t mean I want to add to it.  After years of people gawking (how many years doesn’t matter – focus on the story) I have found a style that lets me be unique without drawing undue attention to myself.  So I wear bright colors to work, but save the sequins and feather earrings for nighttime.

As an example, I will tell you how all of this plays into what I wore yesterday. 



Yesterday's outfit

Yesterday was one of the few days I had meeting outside of my building, so I knew I had to look somewhat presentable.  And it was cold and very, very rainy.  Although jeans or slacks might seem like the warmer option, wet pants take hours to dry and wet tights take less than one.  So, tights it was. 

The question then was: dress or skirt?  I couldn’t find any skirts I wanted to wear with the exception of my grey midi-skirt or my wool plaid skirt, both of which would get very wet and one of which would smell like wet dog until it dried.  I needed something that would dry quickly if (when) it got wet – which led me to the blue dress.  It’s thin enough to dry quickly, but that means it’s not at all warm enough on its own.  Last time I wore it with a black blazer and wanted to try something different this time. 

Enter the kangaroo dress which is made of a thicker, heavier material and would allow just enough of the blue dress to be seen.  Because the heavier dress was shorter, I knew only the blue dress would peek out below my raincoat and when it got wet, it would dry quickly.  The tights weren’t my first choice, but they worked and the booties are my go-to black shoes.  The belt helped give me some shape and the brooch was blue (seriously, sometimes that’s all it takes for me to wear something).

And there you have it – why I wear what I wear when I wear it.

Gracey