I’ve always had a hard time describing my style. I’ve tried, probably too hard, to put it in a nice little category, pin it down with something like “casual chic,” “preppy” or “minimalist.” I’ve created capsule wardrobes to “simplify” my life.

None of that made it easier to get dressed. Throw in pregnancy, motherhood, a move to a new state, and a pandemic, and it felt like I had no idea what to wear anymore.

We all went through a lot of change the last few years. Some had babies, some moved to new places, changed jobs, got married, got divorced, collectively lived through a pandemic, in one way or another we went through something, or a lot of things.

For the last few years I struggled with personal style. It started around the time I got pregnant and felt like garbage. Over time I tried to convince myself it didn’t matter what I wore, and I shouldn’t care. But that just left me feeling, meh. And then I wondered, was that superficial?

My relationship with fashion, and it’s significance as a part of my job made my feelings even more complicated. I realized I needed to strip away the arbitrary rules I created for myself around style. I’ve begun to look at it through a new lens.

If I dress for the life I’m living, and not the one I feel I need to portray on social media, how does that impact what I wear? And how I feel about it.

I’m far less concerned with trends (not at all) and more interested in how to make comfort and style co-exist, without feeling like I need something new every month or season.

I loved this recent essay and particularly this quote from Haley Nahman about fashion and personal style:

Fashion can tell a compelling story about a person, or an era, but I think it’s best understood as supplemental to the essence of either. By framing personal style as an expression of our truest selves, we overestimate clothes, and underestimate people.

Discovering and honing your own style doesn’t require an expiration date or a finish line. Our likes and dislikes, our lifestyles, and our tastes change. Lean in to what makes you feel good, buying a whole new wardrobe won’t do that.

A few tips to get started

  • Take stock of your existing wardrobe. Pay attention to what makes you feel good. Is it comfortable? Do you like how the fabric feels? Does it fit well? This will help narrow down what you like.

  • If something has been sitting in your wardrobe for years and you’ve never worn it or it doesn’t fit, it’s probably time to let it go.

  • Be realistic about your lifestyle and your needs. If you worked in a corporate office and now work remote or in a different setting, you probably don’t need a closet full of suits.

  • Use Pinterest! I started my own wardrobe inspiration board and it gives me so many great outfit ideas (for things I already have in my closet).

  • Stop worrying about trends. The fashion industry drives excessive consumerism, trends are one of the easiest ways to do that.

  • Avoid impulse buys and purchasing something just because it’s on sale. Be slow, thoughtful, and intentional about anything you add to your wardrobe (and shop secondhand too).

5 things in my wardrobe that have stood the test of time

  1. White Tee: I generally say don’t spend a lot on t-shirts, but the quality really holds up on this one, and if you wear them as much as I do, it’s worth it.

  2. Button Down: A piece I wear year round, as a beach cover-up, with jeans, layered under a sweater. I like a more relaxed fit. I’ve had this one for almost 6 years.

  3. Straight Leg Jeans: I just can’t wear super tight jeans anymore. I need comfort and movement. I love this pair because they have a little stretch and you can cuff them over boots or sneakers.

  4. Navy Blazer: I always feel pulled together when I wear this blazer. I love the slightly oversized fit and gold buttons.

  5. Ankle boots: Blundstones are more practical for my Vermont lifestyle and the dress boot (rustic black) is the perfect mix of comfort and style. I went half size up.

Let me know what you think and how you feel about your own personal style evolution over the last few years. Next week will be some more outfits I’ve actually worn lately, and an update on how I’ve organized my closet.

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