All winter I searched for two pairs of flat boots: one in brown and one in black. I didn’t think it would be difficult, but everything I found that appealed to me had a heel. Or was knee-high, which I was trying to avoid. Or wasn’t leather. Or had too many buckles and straps. Or wasn’t available in my size. Sigh.

So I continued to search. Again and again I found myself admiring combat-style boots on other women, but I wasn’t sure if they would work for me.

Style is such an elusive thing. The older I get, the more I want my clothes to reflect my authentic self. Not only do I want them to be comfortable, elegant, and stylish, but I want them to say “me.” Nevertheless, my closet is littered with failed style experiments that I thought would work but … didn’t.

I definitely did not want to buy boots that languished in my closet. But it was also clear that on some level combat boots appealed to me. Would I wear them enough to justify the expense? And if so, were they age-appropriate? How could flat boots not be age-appropriate? More importantly, would they stay in style? I couldn’t decide.

I’m still debating what boots to purchase, but we all need clothes (and shoes!) that give us that extra dose of confidence. For example, I have a pair of black cowboy boots with a red lizard toe cap and red flames snaking up the shaft. Michael 1.0, my ex-husband, gave them to me for my 30th birthday, shortly before we were married. I had told him I wanted something impractical and memorable. Mission accomplished.

I will admit that I was a little annoyed when Michael gave me the cowboy boots. Why didn’t he buy a more neutral brown? But the boots grew on me, and for more than 20 years, I’ve worn those boots whenever I needed to feel like a badass: coffee date with a guy I’d met online who told me I was “plain vanilla,” filing articles of incorporation, submitting my first essay to a major literary journal, launching an open mic and unsure if anyone would attend. It’s amazing how a single item of clothing can make such a difference in our attitude, demeanor, and self-esteem.

I’ve worn those cowboy boot so much that they will soon need to be re-soled. I don’t care what it costs, I’m doing it. A friend reminded me that re-soling probably isn’t cheap and I was, ahem, not 30 anymore.

I said, “Are you kidding? I’m going to wear those boots to my own funeral.”

I was serious. Sort of. I love the idea of wearing cowboy boots with red flames as I stride through the pearly gates to meet my Higher Power. Even if I’m not buried in them, I intend to wear those boots for as long as I can.

Because anything that makes us feel more confident is priceless.

What items of clothing give you the most self-esteem?

Until next time,
Cynthia