the first date

Like many other seemingly bored and lonely twenty-somethings wandering the internets, I tried my hand at online dating this year. I have chatted with and met a plethora of different guys which resulted in a myriad of first dates. This was quite the learning curve because I had only ever been on two first dates before, and neither were the complete strangers you meet via the internet. First dates of course are all about first impressions, and nothing quite impresses (or fails to impress) like the clothes you wear. In the beginning, deciding what to wear on a first date was a bit of a struggle for me. Like most humans I am multi-faceted and do not perfectly conform to any particular label: girly, nerdy, sporty, artsy. All of my personalities could make up a girl band or a rag tag group of superheroes or a rag tag group of superheroes who masquerade as an internationally famous girl band (which I’m fairly certain is the premise for the next Cheetah Girls movie).



If I were to hazard a guess I would say those who know me understand these different sides to me and see how they reflect in my personality and outfits. However, I have recently learned this isn’t always true. The other month I was in a social setting with people from work. I forgot my purse in my bosses car and when I told him I needed to go back and get it, he was completely confused: “What?? A purse? You have a purse??”. I don’t think I’ve ever seen him struggle so hard to grasp such an easy concept as owning a purse. When I reasonably asked him what the big deal was he just said he didn’t think I was “into that kind of thing”. I assume by “that thing” he meant “being feminine”. I feel the fact that I write a fashion blog and women’s pockets hold jack shit means that yes of course I own a purse.



This is all to say, if even my boss of over a year couldn’t comprehend my multiple layers (similar to ogres and onions) how was I going to convey this complexity to my date? The west coast is a pretty casual place, so although I love wearing skirts and dresses, they might come off as a bit much for a coffee date. On the other hand, I feel wearing a plain shirt and jeans just isn’t me. So somewhere in between is this outfit: the shirt and pants say “I’m casual” while the mix of indigo and purple says “I’m bold and put some thought into this outfit”, and the delicate* floral print says “I’m feminine” while the minimal makeup and hairstyling say “I’m laid back but still like to look nice”, and the bag** and jacket say “I have things to hold” and “I’m cold” respectively. After my clothes finally shut up my date and I can exchange awkward greetings and niceties about the weather in peace.

* This aspect of portraying delicateness is particularly important if the date includes food consumption. I eat a lot. and quickly. and not delicately. I have never seen myself eat, but I’m sure I would fail that portion of “how to be a lady” class from the olden times.

** The hilarious Iliza Shlesinger states the clutch is the only viable option for a first date because it signifies how little baggage you are bringing into a relationship, but I still haven’t successfully figured out the clutch on a bike situation.



  • Shirt: Clothing Swap (free)
  • Camisole: Salvation Army ($12)
  • Bag: Pipsqueak’s Consignment ($12)
  • Jacket: Pipsqueak’s Consignment ($20)
  • Pants: Clothing Swap (free)
  • Scarf and Necklace: Gifts
  • Boots: H&M  ($20)
  • Photography: 🙂 

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