woman writing

I really believe everyone has a style that works for them, things that are flattering and make you feel comfortable and, most importantly, make you feel like you. We all go through bad fashion periods, though. Looking back on my own bad fashion periods, I think many people go through these awkward phases as a result of insecurity. Yes, there are people who genuinely don’t know what’s flattering or just haven’t found a style to suit them yet. That aside, what is jumping on every passing trend if not insecurity?

I’ve written before about moving to a different region of the country and the way it made me feel awkward about my personal style being too stuffy/dressy. Being in my mid-twenties and not really knowing anyone, I wanted to fit in so badly. Too badly to just wear the khakis and shrug.

After undergrad, I recognized right away that my college girl wardrobe wasn’t appropriate for a full-time working adult starting to build a career. I owned a lot of revealing tops and skinny jeans and Bestey Johnson dresses and Steve Madden slides. (Can you guess my birth year based on this list?) Even to go out with friends on the weekend, these things just didn’t seem quite right anymore.

Kudos to young me, I donated the college clothes and approached replacing them as an investment opportunity. Looking back, I think my entire wardrobe was from J. Peterman at one point. Of course, my tastes/body type have changed in fifteen years, so several of the investment items have been resold or donated. I still have a lot of the core items, though, and they’ve held up really well. I think the 1947 dresses will last until 2047!

But, as I already discussed at length, these classic and well-made investment pieces stuck out quite a bit when I moved. Art school is not the place for classic fashion – as the fictional Sutton and I both discovered. Neither is every workplace, especially arts-related ones, which is when I tried to change things up with disastrous results.

I mentioned my hideous long skirt* era briefly in Part I. This is where I circle back to insecurity driving poor fashion choices. A coworker was very into buying clothes at thrift stores, which had never really interested me. I like to get vintage/antique home décor items this way, but prefer eBay/the RealReal/Poshmark for secondhand clothing.

Anyhow, I started shopping for hideous long skirts at the thrift store, and they were so cringe. I also got really into making my own clothes during this time. I’ve been sewing for many years and am pretty adept at making things like pillows, curtains, etc., but clothes, especially for women, are very hard to make. It was a fun hobby, but I definitely should not have taken my amateur creations to the street. Or to formal events…

I was about 30 years old while this was going on. Old enough to know better, in other words. This wasn’t about ‘finding my style’ because honestly, I’ve always known what that is. This was me trying not to feel awkward, but subsequently looking weirder and more awkward than I have at any other point in my life. All in all, the weird skirts/handmade clothes era only lasted about a year and a half. (Part of that was maternity, and let’s face it, a long skirt is pretty darn comfortable at that point.)

Of course, there are many situations where you will want/need to fit in, but there are ways to do this that don’t involve completely reinventing yourself. If you do feel horribly uncomfortable being yourself somewhere, maybe that’s not the right place for you. Otherwise, as long as you use common sense and dress appropriately for the occasion, there’s no need to waste money and energy trying to look the way you think everyone else would prefer.

*Please note that I have nothing against maxi skirts that are well-made and flattering. I own some wool and cashmere ones that I love. This story isn’t meant to trash maxi skirts, thrift stores, or the people who enjoy them. It’s simply about me not being authentic in the past.