On Fashion Confidence

Over 40 and finally in a life situation to dress to reflect my self-perception

A quick browse through fashion content gives this message: Wear what you want. Fashion influencers for women over 40 seem to especially declare this, except for when they’re explaining how to dress to meet conventional expectations.

I agree with the “wear what you want” message. I do, however, think there’s a missing perspective. Or at least, a perspective that I haven’t discovered yet or that gets overshadowed.

Our life situations can affect what we feel comfortable wearing. This seems obvious, but I think acknowledging it can get lost in the body-positive, no-age-restrictions messages.​

See the image at the top of this post?

This is how I’ve always felt - bright and slightly unconventional. What you can’t see are the double helix piercings, the two sets of lobe piercings, or that my lip color is a bright red-pink. Right before this photo, I was wearing six rings and 2-inch hoop earrings. I love dramatic winged eyeliner and I don’t care if the angles don’t match perfectly. 

Now look at this photo.

Here is my story.

I felt good in this outfit, too, but when this photo was taken, I would have never dared to wear the mesh outfit in the first photo

When I worked in my previous job, this is how I felt most comfortable dressing on my days off. 

These are both day-off photos. 

In my previous job, even on my day off, there was a chance I would run into a client. I felt most comfortable if I answered these questions when deciding my outfit for my days off:

• Would I feel awkward if a client saw me wearing this? 
• If I saw a client today, then later this week had to have an uncomfortable conversation with them, would what I’m wearing now affect how they view me?

Those questions may not be fair. In a perfect world, we wouldn’t have to ask these things. People would be able to compartmentalize and recognize that all people are multi-faceted humans, regardless of their jobs. Unfortunately, we live in a world where people are judged by how they look, even in their time off. 

That reality meant that for 10 years, I tamed the true expression of my sartorial self. 

Do I regret that? 

No. Making those choices gave me more confidence in a high-stress job. 

Am I very happy that I no longer work in a position where it feels like all eyes are on me? 

Absolutely. 

Do I still sometimes dress like the second photo?

Sure, when I’m hiking up a mountain.​

So what? 

All this to say, if you, too, make clothing choices based on your circumstances, and those choices don’t reflect the true you, I commiserate. There’s only so far haircuts and accessories can take you. Moreover, in some communities, personal clothing choices are closely monitored. Deviating from accepted norms has intense relational fall out. I get it. That’s a hard place to be in.

At the end of the day, this is my addition to the “be yourself” conversation: Don’t feel like a sell-out for doing what you have to. Don’t resign yourself to nothing ever changing, either. The wonder of being human is how flexible we are. This year, we comply. Next year, we resist. To be human is to grow, change, adapt, and rest. Let that be true of your fashion choices, too. ​

Fashion Inspiration

• Blue Plaid Vest Spring/Fall Capsule Wardrobe
• The Macaw and I Agree
• Three Ways to Style the Sinclair Yasmin Dress
• Tie-Dye Dress Spring Capsule Wardrobe