Allow me a philosophical moment, if you will.

When you get ready to go to work, who are you looking to please with your mode of dress? Your boss? Your customers? Yourself? Your coworkers?

I’ve held a variety of jobs and I’ve noticed recently that the way I dressed has changed with the job. As an assistant buyer in an office with primarily other women where my odds of promotion were slim, I found myself really dressing down. We had sales reps in the office regularly, but they were rarely there to see me. There didn’t seem to be much reason to dress up – heck, I had a coworker who dressed almost as appropriately as Erin Brockovich. Tell me, what would be the point in wearing something less comfy and easy than sorta wrinkled Capri pants and flip-flops? Was there a point in ‘dressing for the job I wanted’ when the job I wanted was likely to be filled by someone from outside the company? Comfort won the day at that job.

After that, I taught high school students. Obviously I spruced up the wardrobe a bit but I still ended up in flip-flops in the middle of winter – of a ‘dressier’ variety, sure, but still. As for the rest of my attire, I was keenly aware of the appropriateness of the clothes I wore. I always sorta hated my 9th grade teacher who never seemed to be wearing a bra. The boys couldn’t pay attention to anything else. So I basically ended up looking like a 25-year-old wearing clothes intended for a 65-year-old. Propriety + Comfort swayed my wardrobe decisions as a teacher.

As a sales rep, I began to hone my attire into something younger but polished and professional – I was seeing customers regularly and wanted to impress. Of course, there were also many days that I ‘worked’ from home in my pajamas, which was nice, but only for the PJ’s. I pretty much hated working from home for all other reasons.

Now I’m in a fairly visible part of a college bookstore, work with a bunch of guys, and feel like the future is promising. My wardrobe contains a lot of fancy skirts and colorful blouses, jewelry and kitten heels. I love it. I feel confident – more confident than I’ve felt in past jobs. Could be that I’m well suited for the position in general, but I’d like to attribute some of it to the clothes.

Also, the shoes. I love tapping across tile floors in my heels. Probably has something to do with the fascination I had for ‘grown-up girl’ tap shoes as a little dancer. I wanted some so. bad. All I can say is that it’s a good thing flip-flops aren’t allowed at my new job. I am secretly (or not so much secretly) a fan of a slightly raised bar. Casual Fridays are wonderful in a way, but to be honest, my jeans are pretty uncomfortable and were purchased during my teaching year and therefore ride right above my belly button. This is not attractive, nor is it comfortable. I may forego the jeans next week in favor of my adorable denim dress (also purchased during the teaching year, but doesn’t make me look like an old woman). Yes, I think that may be the way to go.

So I’m not sure how to answer the questions I posed at the beginning of this post. I guess I’d say, mostly, I wear the clothes I wear because they are the clothes I want to wear. There’s the component of being around customers, wanting to give a good impression to my employers, as well as feeling good in them. But I guess it’s primarily a personal choice for me, in the end. I’m just glad I don’t have to wear a uniform. Three cheers for that!