Not having a dress code is awesome, but also scary, as creativity craves constraint. It can be difficult to figure out what to wear when you can wear whatever you want. The past few months have enabled me to be innovative both with my work and clothing while still looking (more or less) as professional as a content writer working needs to look. As such, I've created a list of wardrobe staples that run the gamut from "preppy super-business-casual" to "lazy college student".
Oxford Shirts: Startup or not, no working wardrobe in Boston is complete without a pearl statement necklace and some button-down Oxford shirt layering. The difference here is that I can do it with jeans or leggings and still manage pull off an effortless classic look. These outfits mirror those of the preppy COO and sales guys in my office, creating a seamless flow of synergy while listening to yacht rock.
The layering look is very scalable--black pants, jeans, a skirt, or colored corduroy if you're feeling crazy. It's a responsive look as well. This look takes you from day-to-night, keeping you warm in a cold basement office yet giving you the ability to shed a layer if you end up going out for beers after work. It's a good style to have in your pipeline, sitting pretty at the intersection of preppy and cool.
Scarves: Fall is in full swing so I find myself circling back to scarves. Aside from keeping me warm, scarves are also a good way to distract people from the fact that you're wearing leggings. Also, since startup talent is fueled on coffee, scarves are good to catch or cover up the inevitable coffee stains on your shirt.
While scarves are great, they have limitations and should not be worn while playing foosball or ping pong. No one needs to be distracted by your scarf getting caught on a roller arm.
Layers: Non-Oxford layering is another fashion strategy while working at a startup. It enables you to adapt pieces of a previous corporate wardrobe without looking like you're too good to "get shit done". It's also a way to increase the bandwidth of that puffer vest that you struggle to find ways to wear. If you work with all men, layers are game changer, confusing men and making them less likely to notice that you wore the same thing twice in a
week month, if they notice clothes at all.
Ripped Jeans: I've worn ripped jeans more times that I'd like to admit. Between the comfort and stretch and ability to fold up well with my booties, ripped jeans are a low hanging fruit. I try to pair my hobo jeans with a statement necklace and jacket for a more put together look...or just give up on life. Nothing says pivot like embracing the 90s grunge look with a buffalo check flannel and a pair of Birkenstock clogs.