Meet Maddy, our 18-year-old June GOTM who no doubt gives Carrie Bradshaw a run for her money.

This (newly) high school senior has had quite an education in fashion- from her chic model mom and her entourage of fashionistas, editors, and designer friends, to her exposure to international fashion at Culver Academies, a t-shirt line, hand-made jewelry collection and now a summer at Parsons in New York studying fashion design with long-time best friend, Britt.

Watch out upper-east-siders.

We have never seen a girl with such style dress as comfortably as Maddy- and we are so jealous!

“I bought these in the Carribbean and they are so comfortable- like sweatpants,” she tells us of her cross-button slouch pants.

This style has been all over the runways and we think they are completely under-worn. Drape front trousers are flattering and you do not have to spend a fortune to get the look. Try this pair from TopShop for only $80!

To translate this look from day to night, Maddy paired her cream pants with a short taupe 3.1 phillip lim silk top and her mother’s oversized black Birkin. If you can’t find these exact pieces, we suggest trying this A.L.C. Sleeveless Top from The frayed banding at the sleeves and plackett give this top a Lanvin look and the length is just right.

Balancing the monochrome up top, she wore a pair of Zena┬ásnake skin sandals from Jimmy Choo’s new collection for a bit of texture. Check out the lucite heels!!!

Check back with us next Tuesday for more looks from Maddy’s summer wardrobe.