Something I’ve struggled with in recent years is defining “my style.” I’ve always considered myself pretty preppy, but I’ve felt that shifting a little as I find myself reaching for neater, more tailored pieces–like my favorite cropped tweed jackets instead of a blazer, or a pair of Stubbs instead of my worn-to-death boat shoes. It’s interesting to see how things change as life changes.

In my early years out of college, living in D.C., sometimes I feel like I dressed as though I stepped out of The Official Preppy Handbook. In fact, one memorable day I inadvertently dressed almost exactly like this illustration at left.

Not sure if that was my worst moment or my finest one, haha. Anyway. While I do still favor the Fair-Isle-henley-over-turtleneck look, I’m attempting, at least, to step away from this and look a little more like… well, like I’m myself, and not like an illustration in a satirical book.

This is another part of my goal to edit and streamline. I have a ton of things I no longer wear because they are too “out there” for me now. Oddly, it’s not the items you’d think, like my grandmother’s bright pink needlepoint slippers I wear nearly daily in spring and summer. But while I have a good sense of what’s too “out there,” I’m finding it a bit harder to really narrow down what feels most comfortable to me. I’m drawn to more tailored pieces now, but sometimes I don’t find that tailored pieces are the right fit for everyday wear. But then I’m tired of wearing leggings and oversized shirts! I guess I’d love to look like Elizabeth James from The Parent Trap–pulled together and effortless whether in London or at the Napa vineyard. But let’s be real, don’t we all want Elizabeth James’ wardrobe?

What I’m really trying to do now is figure out: 1) what I feel most comfortable in and 2) what makes me look good. Not runway-good, but just what suits me. It’s harder than you’d think, especially without help! I used to love going into Ann Mashburn in Georgetown and working with the fabulous team there to figure out what would best suit me. (My wallet definitely did not love that!) It wasn’t necessarily the items I’d lean towards (shift dresses, for one), but with help, it was so easy to pick things that made me feel happy when I wore them! Sometimes you need an outside eye, and people who know you well.

Unfortunately (fortunately! screams my wallet) when I left D.C. I stopped having that experience in regards to clothing. I haven’t again found a shop with such helpful people, and while it’s great to be able to order clothes online, I miss that personal connection. It’s made shopping a lot less enjoyable and a lot more difficult.

While online shopping is definitely convenient, the great customer service I’ve always experienced at certain stores makes me really wish that in-person shopping was the standard again, even without the pandemic. It’s wonderful to become friends with people (as someone who worked in retail at one point, I definitely valued those relationships!) and work with them to define your style.

But it’s not only that. Supporting smaller businesses who create and sell handmade items, or items made with care in one location and not all over the world, is a way to directly impact the lives of actual individuals, instead of a trillionaire who really does not need any extra money. Not that this is a rant about that, but, well–I’d like to start shopping carefully and responsibly.

This ties back to the “fewer and better” thing–fewer things and better things. I’d love to step away from endlessly searching for “the right” item, whatever it is, and stop trying out so many variations of the same item only to be disappointed each time. As well, I’d love to completely stop my reliance on big stores and ecommerce sites (cough*theonlinestorethatshallnotbenamed*cough*) and support smaller businesses. Much easier said than done! But it’s a start. We’ll see how this turns out…!

Image via The Official Preppy Handbook.