Head-to-Toe Red and More Outfit Ideas from Anna Gray

  • Day 1: I love this shirt. And yes, I am always a little worried about the tassel bits getting stuck in a cab or subway door.

    DVF shirt, Ohlin D jeans -- another option here, Truss bag, Dieppa Restrepo loafers
  • Day 2: My boyfriend's sister runs the Paris party Cicciolina so we have at least five of these shirts. They go with everything. Despite its length and bright pattern, this skirt also goes with everything.

    Cicciolina party T-shirt -- another graphic T-shirt here, DVF skirt, Anya Hindmarch bag, Kurt Geiger shoes
  • Day 3: These pants are from my favorite Etsy store. They sell only menswear and the model is amazingly goofy (seriously, check him out). As for the bag: Khoi Le and I have been friends for ten years and this is from our first official collaboration, though he's been sewing bags for me for the entirety of our friendship. We wanted to see where our styles intersect. The three bags are interesting takes on classic shapes, are really easy to wear and come in this beautiful rusty suede—  a surprisingly versatile color.

    Vintage L.L.Bean pajama shirt -- another here, vintage suede pants -- similar here, Khoi Le x Anna Gray bag, Converse shoes
  • Day 4: An outfit for running around town. My friend Lola Abbey is obsessed with puffballs and uses them to make everything from these earrings to chokers to phone cases. V whimsical conversation starters.

    WHIT blouse -- another here, Vacation NYC jeans, Repetto flats, OAD bagDady Bones earrings
  • Day 5: I love tucking baggy pants into boots because I saw a very chic older woman wearing the combo in Bergdorfs once. My roommate (the inimitable Brie Welch) rolls her eyes and says I look like a circus ringmaster. Whatever.

    J.Crew sweater, my mom's pants -- similar here, Rochas boots -- another here, Olympia Le-Tan clutch, vintage neckscarf -- another here
Haley Nahman | March 13, 2017


Anna Gray, writer and model living in New York, is the woman behind “Things I would buy if I didn’t have to pay rent,” which is a poetically appropriate newsletter for a writer and model living in New York, isn’t it? It’s also one I viscerally relate to on title alone. There’s nothing more relatable in this city than wanting stuff but paying New York rent instead.

Her week of outfits, documented above, strike a similar chord — that oxymoronic intersection of relatable and aspirational. Take Day 1, for instance, where she manages to take an old formula like jeans, loafers and a white button-down and make it something really special. Like something you might want to wear right this second. She’s walking proof that interesting outfits don’t need to be complex.

Something about Anna’s closet feels inviting and generous. She not only makes cool look easy, she shows you how. Click through to see for yourself.

Check out Anna’s newsletter Things I would buy if I didn’t have to pay rent and follow her on Instagram @annazgray; feature collage by Maria Jia Ling Pitt.

  • don

    Love the all-red ensemble and the goofy model at Etsy!

  • Lindsey Kanas

    Funny with the etsy model… I love him too and have him saved in my faves! As soon as you mentioned “him”… I knew it had to be that shop… Love your insites and point of view… by the way.. not a ringmaster.. A pirate..

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