Founding While Female

Founding While Female

This is not a post about discrimination or equal opportunity. It’s a post about fashion.

Turns out, this is actually an emotional issue. It’s not just about looking good – it’s about feeling good, and trying to find the balance between the two. This is something I’ve struggled with for years.

I’m a 36-year old woman, and I don’t know that I’ve ever figured out how to make my hair look good or found clothes that are professional without making me feel like I’m playing dress-up. I have no idea how to put on makeup – I didn’t even wear makeup at my own wedding. A few years ago, I finally donated all of the heels in my closet because I decided it was time to get real and own the fact that every time I have to put on a pair of shoes and it’s cute vs. comfort, I choose comfort. I feel most myself in workout clothes or pajamas, and I consider it a win if I can get out of the house with minimal dog hair on my legs (pro tip: just walk around in your underwear for as long as possible before putting your pants on and scooting out the door.)

This never really bothers me… until I’m trying to feel “professional.” The thing is, I don’t WANT to learn these things. I don’t WANT to spend boatloads of money on clothing or hair products. I don’t WANT to take an hour blowdrying my hair and putting on makeup every morning. To be clear, I’m not judging women who do all of these things – I’m often a little jealous of them, in fact – but it doesn’t feel authentic to who I am, so I don’t do it.

When it comes down to it, if I manage to look fabulously professional but doing so makes me feel completely fake, I’m not bringing my best self to whatever meeting or presentation I’m attending. I end up feeling so uncomfortable in my own skin that my inner voice becomes loud and distracting. I’ve found that if instead of going for “professional,” I strive for “presentable,” the inner voice is a little quieter. It’s still there – but it doesn’t tell me I’m a fraud or not worth listening to.

I know this about myself, and YET… every. single. time. I have to get dressed up for a work-related event, I have a mental battle. The higher the stakes, the more tempted I am to go out and purchase new clothes, get my hair done, and turn myself into the woman I think I need to be. I have to remind myself that the cost of this approach would be more than monetary.

I’m not sure how to solve this. In my twenties, I guess I assumed I’d figure it out once I got older, but that hasn’t happened. If anything, I feel MORE anxious about it – because at this point, it feels like the ship has sailed, and I’m caught in this weird “too old to be too trendy but too young to be completely out of style” place. I’ve considered seeking out a female mentor to ask about how best to approach my first-world struggle with fashion vs. authenticity… but just the fact that I’d be asking for advice about clothing somehow feels belittling — like I’m not placing as much value on her intelligence as on her fashion sense.

I can’t be alone in feeling this way… right? And men don’t worry about these things… do they?


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Close Menu