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.
Yup, my uniform of late: black skinnies, chambray, ankle booties, scarf. P.S. Love your Made in the USA tee. XOXO http://americanmadeguidetolife.blogspot.com/
I seriously need to invest in an oxford shirt to wear with a statement necklace…or a denim shirt and your AE top to wear with one, because that look is flawless! You always look so cute. I never would have thought to wear Birk clogs with cuffed jeans before, love it.
Congrats on the new job gurlie! Loving all the scarfs and different combos. Isn't no dress code the best? I've worked in both environments, and love not having a dress code. I still dress up some days, but love the freedom to dress how I'm feeling that day.
Love all of your outfits! I think I love the oxford outfits best for work but everything looks so comfy and practical!
It's so hard when you can wear whatever! I feel like I'm judged when I wear something nicer to work. I need to get some Oxford shirts though… That is a staple that needs to be added to my wardrobe.
You look cute in anything! Love how you slipped in some techie lingo. 😉
You're sooo cute! I love all of your outfits. I always look at converse and then never buy them but I think this is finally the year I shall get them. I love the ripped jeans, especially with the flannel and the birkenstocks! That's the one thing they don't like us to wear…other than that it's fair game and I love it. I wish we could layer more in Florida, but it's just now
What awesome outfits!! I need a new wardrobe.