The year I turned 40, I instantly became more self-conscious about my clothing choices. I had always liked fashion, but I didn’t want to be one of those women who looked like she was trying too hard to hang on to her youth (aka: “mutton dressed as lamb”). Plus, with two adolescent girls, I didn’t want to embarrass them by trying to look like their peers.

At the same time, I like clothes. I like to be comfortable. I like what I like and I don’t like to be subjected to “rules” that are determined by my age. Over the last several years, I’ve become more comfortable with determining what’s right for me. And I think I walk that tightrope between fashion and appropriateness pretty well. But if I start to lose my balance, you can bet that my now 18- and 21-year-old daughters will extend a hand to save me from making a serious style misstep.

Case in point: Last year, I was obsessed with a leather sheath dress from Banana Republic. It was a classic style in soft brown leather—more polished and unexpected than the predictable black—so I thought I could put a professional spin on it and wear it to the office. More expensive than my usual wardrobe choices, I watched the website for a sale. First it was in stock, but not on sale, then on sale, but out of stock. Finally the planets aligned: It was in stock and on sale. I ordered it and waited impatiently for my new purchase to arrive. A few days later the package was delivered. I rushed upstairs to try it on. It really was a lovely dress, with buttery supple leather. But when I tried it on and looked in the mirror: Meh. Despite the sizeable investment, it didn’t transform me the way I’d hoped. And at my age, I can’t afford to let my fashion dollars sit idle. Or was I just being too critical because of the hefty price tag? Looking for a second opinion, I walked downstairs and modeled my new purchase. “Whaddaya think?” I asked my husband and daughter. My husband (ever the diplomat) answered, “It’s nice.” My daughter—on the other hand—responded, “Mom, you look like a couch.”  With that appraisal, I had to face the cold hard truth: I wasn’t fashionable, I was furniture. Needless to say, back went the dress…

A fashion miss is one thing, but I take other “don’ts” more seriously.

For example, the fine line between “attractive” and “suggestive.” Having a rather delicate décolleté (i.e., the “girls” are truly “girls,” not full-grown “ladies”), I don’t have to worry about excess cleavage. But is this skirt too short? …this dress too form-fitting? …these heels too tall? I always struggle with finding the right balance.

Years ago, when KitKat and I worked together, if we were trying to evaluate whether something was inappropriate for work we had a foolproof test: The Bob Miller Axiom—named for a somewhat salacious coworker. If you were wearing anything borderline, you could rely on Bob to compliment you on it. And then you knew beyond a doubt that you probably shouldn’t wear that outfit to the office again.

In fact, when my husband and I ran into Bob and his wife on the beach as part of a work incentive trip, he even complimented me on my bikini. Now everyone knows that if you’re among coworkers in swimwear, you should assume a Cloak of Invisibility. That is, you do not acknowledge the aforementioned swimming attire, you don’t take candid photos and post them on Facebook, and most importantly, you don’t compliment the 30-something coworker’s taste in swimwear while you’re standing there with your 60-something wife.

With all these perils, you’d think it would be easier to just choose a “uniform” and stick with it (and as someone who spent her formative years in parochial school, I’ll admit to still having a bit of a thing for Black Watch plaid). Yes, while playing it safe would certainly be easier—and shave some time off my morning routine—I know I’ll continue to walk the tightrope. Because fashion is fun. Fashion is expressive. And when you’re in Marketing, you can justify spending more than you should on clothes by telling yourself your chosen field requires a stylish career wardrobe … at least that’s the creative rationalization KitKat and I employ. After all what better way to subtly underscore your keen grasp of pop culture and trends? Hey, whatever pays the (shoe) bills!  😉