What you really need to ask yourself is: do I look like a power lesbian summering in Nantucket? The answer should be, “Yes.”

I feel like I could totally life-partner with Rachel Maddow in this outfit. The black pant, rather than a lighter-colored chino, makes it a little more boardroom appropriate and would nicely complement Maddow’s hair. And you know Ellen would wear the balls out of a pair of Chuck Taylors with her summer suiting, a look she probably made cool back in college, well before Jeremy Piven & Co. hopped on the bandwagon and ruined everything.

Up top we’ve got a pinkseersucker shirt from J.Crew that I’m literally wearing with a Band of Outsiders repp tie with boats on it, wHaT!? Let me explain: I was in J.Crew one day because I know they make XS’s, looking for a basic white or dark navy oxford and striking out. Then I saw this on the rack and thought it couldn’t hurt to venture out of my comfort zone. #TakingChances ( <– Celine Dion reference, anyone?) It fits really well and looks even better wrinkled than ironed out, which means it’s super easy to dress up or dress down. (This is it dressed down.)

And then we have these boss-ass (are we hyphenating that now?) Warby Parker frames. Ugh, aren’t they so sick? Someone at work said I looked very “weekend in the Hamptons” in them, so basically she called me an asshole…but a hot one!

Shot by McArthur in Washington Square Park, a great place for:

  • Watching hot men do things
  • Instagramming iced coffee
  • Instagramming a cute picnic
  • Taking selfies
  • Being like, “this is like, my favorite park.”

P.S. Here’s a beauty tip – don’t wear a tinted moisturizer on the back of your neck (it had SPF in it and I didn’t want to burn!) It will ruin the collar of your shirt and just generally be disgusting to look at.