I attended this event last month which had me scrambling at the last minute with a wardrobe “crises” when I realized that it might be a dressier affair than what I had first thought. My friend Nichole and I traded emails throughout the day, throwing out outfit possibilities and changing our minds multiple times, down to the last few hours before the event. It was like being back in high school.
I know everyone goes through this experience where you think you “have nothing to wear”, but I quickly realized during that moment of panic that I’m so not prepared to attend anything that requires me to dress up in formal clothing. I can manage business casual if I have to and I can certainly come up with an outfit for a nice dinner, but my lifestyle of freelancing at home and conducting most client meetings via conference calls just doesn’t support the need to have dressy clothes. What made it even worse was that the few items I had that I always thought were my go-to dressy outfits neither fit well anymore or were very badly outdated. This includes a beautiful silk Mayle dress that I bought at a Barneys Warehouse Sale 12 years ago that just doesn’t really fit me all that well anymore (oh yeah, they never really tell you that you can get broader in the shoulders permanently it seems after pregnancies, do they?). I also had saved these fancy expensive strappy high heel sandals that I bought for a project launch party we held one year at MoMA 12 years ago, but they too were completely outdated (we’re talking severe square toe beds from the late 1990s). So off to the Goodwill pile they went.
So now what? I managed to come up with an outfit for that evening, but just shook my head at the ridiculousness of someone my age not having anything remotely appropriate in her closet for anything dressy. I’ve set a goal to stock my closet with at least 1 dressy appropriate outfit for cold and summer seasons whenever I have the extra budget to do so, which means online window shopping!
So on that day of outfit panic, I used a coupon code to buy these short Madewell high heel booties. They’re not super dressy, really, but they can certainly be dressed up more than my high heel clog Swedish Hasbeens, that’s for sure. I’ve been wearing them a lot since I’ve gotten them and I love them. They are perfect with jeans and dresses.
Bur for more fancier shoes, I am sort of at a loss because I am not a stiletto or pump wearing kind of person, but I do enjoy thinking about these Michael Kors strappy sandals, but have to admit that I would probably be a lot more comfortable wearing something like these high heeled mary janes from Frye (in black). I do have vintage navy Ferragamo t-strap heels, so I think my search will be more focused on dressy sandals.
So…dresses! Why is finding a dress so hard? I really LOVE this Maje dress, but why so short? I don’t necessarily have a problem doing short, but I really wish this dress was at least a few inches longer because then I think it’d be perfect. Too bad!
Now if I were a person of a certain budget I would wear pretty much anything from Ann Demeulemeester. Even though these black dresses here and here are styled down (and it’s styled perfectly in my opinion, I might add), I think they would work as cocktail dresses with the right shoes and accessories. But I’m not. So…moving on…
On the other end of the spectrum from these black dresses is this flapper inspired beaded dress. I can’t help it. I like shiny and beaded things. I think the model is standing a little weird and therefore making the front of the dress a little awkward looking, but the back is beautiful. I can’t really tell whether I love this particular dress or not, but I’ve learned from window dress shopping that I gravitate towards simple black dresses or beaded neutral flapper craziness. Ok!
Now, you can’t be all fancy and lug around your everyday canvas tote bag or even your casual leather shoulder bag. You just can’t. Luckily I do have a few options for dressy handbags which I inherited from my mom from her fancy bag carrying days in the 60s, but I am mesmerized by this woven metallic clutch from BCBG. I can’t stop staring at it and I want to play Q-bert on it. For something less flashy, I love this simple Calvin Klein evening clutch. That rose gold color is really pretty, plus it’s shiny! I told you, I like the shiny!
So I haven’t actually bought anything yet other than those boots so I’m not any more prepared for a dressy occasion than I was last month, but I’m still looking. It might also require actually shopping in person in actual stores, something that I usually don’t have much time for or really enjoy all that much anymore. We’ll see…I will keep you posted.