In September, I made a groundbreaking leap and changed careers. I went from being a conservative lawyer to a creative career in content marketing at a startup (more on this another time).Since I started working for a small startup, my work wardrobe has changed significantly. As in, I can pretty much wear whatever I want.
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.
T-Shirts and Converse: Last but not least is the most comfortable of all of these styles and the one that will help you blend in with developers. Depending on the culture of your office and personal style, you may be able to wear t-shirts, sneakers, and ripped jeans and still be taken seriously. Since the CEO of my company wears Converse, I took the opportunity to rock them a few times as well, both times with cardigans, because I’m disruptive like that.
As you can see, you can pretty much wear anything within reason and still be startup chic.