Style Files: Bringing Back My Real-Life Outfit Diaries
And a walk down memory lane re: the Internet and me.
Let’s rewind to the very beginning of my history sharing my outfits on the Internet…
At 25, I called it quits on my medical marketing job and dropped out of my night school MBA program. Then I tried (and failed) B2B sales and corporate fundraising, and softly landed in a part time gig helping my mother-in-law with social media for her flower shop. It was an anxious time of change and upheaval, and in the middle of it all, I discovered a delightful distraction: personal style blogs.
If you were around during the Blogspot/Blogger personal style blog heyday, wasn’t it a lovely time? I remember cozying up every evening with a glass of wine and my RSS blog reader, clicking through everyone’s posts of what they wore to their 9-to-5s. It was a bustling community of regular people, sharing their everyday lives through unedited online outfit diaries. Everyone was out there pairing Target basics with unique thrift finds, re-wearing their favorite pieces, print mixing with reckless abandon, and DIY’ing the designer stuff they couldn’t afford. (Remember when buying full-price seasonal Anthropologie or J.Crew meant you were rich, hunny?)
I was inspired and wanted in on the action. I spent days thinking about my blog name. The country was in the middle of an economic crisis — just as I was in the middle of a quarter-life crisis — and without my corporate salary, I didn’t have much disposable income to spend on clothes. I wanted my “little corner of the Internet” to be a creative outlet to catalogue my daily outfits and share budget-friendly styling tips. I finally settled on A Pretty Penny; as in, you don’t have to spend a pretty penny to look cute! (It made sense in my head at the time, but mostly people just thought my name was Penny.)
I hit publish on my first post in the spring of 2010, and kept it a secret from everyone but my parents and closest friends. It felt weird, and a bit self-indulgent, to post photos of myself online every day. I think I started my blog before I had an iPhone — mirror selfies definitely weren’t a thing yet —which meant my husband and I had to bop around near the flower shop with our digital camera, looking for spots to take my daily outfit shots. If someone drove/walked by these amateur photo shoots, I froze like a deer in the headlights. But despite me bashfully hiding my new Internet hobby from my IRL community, my little blog grew — and I eventually stopped having flutters of anxiety when people in my real life told me they were readers.
A Pretty Penny had a very fun run of success in my late 20s. There was a point when I considered making a go of blogging full time, but we had bills to pay and monetization was a relatively new concept at the time (this was pre-influencer and the wild frontier of early affiliate marketing). My mother-in-law was ready to retire, so my husband and I decided to go all-in and take the reigns of the flower shop instead. I rebranded my blog to keiralennox.com and continued posting as a hobby for years, until the last of the loyal blog readers finally moved over to Instagram.
I used to look back on that fork in the road in a Sliding Doors kind of way, wondering what our life might be if we transitioned into the influencer economy instead of local small business ownership. Now it’s 15 years later: we transitioned the family business into the small boutique floral design studio of my dreams; I’m a solo designer making my own schedule and creating beautiful things for a living; and I still sporadically share my life and style online. Life is very good living a little less online.
Oh, and now I’m 40 years old.
There’s something about hitting the big 4-0 that makes me nostalgic for that pre-influencer style community. It still feels a little weird posting photos of my outfits online, because I’m not a fashion girlie and my 20s were a long time ago. But I still love getting inspiration from other ‘normies’ - and I think I have a pretty good knack for styling everyday basics that may be helpful if you’re looking for ways to make the most of a minimal wardrobe.
I thought about knocking the dust off my blog, but Substack feels like the place to be right now. It also reminds me of the creative early days of Blogger; a lot of the Substack creators I follow post their own real-life outfits, with fresh points of view and special details that reflect their unique personal style. (As opposed to the cookie cutter, trend-led sameness that tends to dominate other online spaces.) So when I decided to dip a toe back into posting my own outfit diaries this year, Passing Notes felt like the perfect place to do it.
I have so many thoughts about how my personal style is evolving in this new decade, and why editing down my wardrobe is changing my aesthetic for the better. And while I’m older with more resources than my early blogging days, I’m still pretty frugal about my wardrobe purchases; I don’t think you need to spend a lot of money to have great style. I’m hoping to share all this and more right here, in the new iteration of my old blog series, Style Files. If you’re into that, subscribe to get fresh notes right in your inbox.
TTYL!
Keira