Kaitlyn shows us the right way to pull off the athleisure trend, and this look is not only comfortable, but it's multi-functional too. Here we started with the cute athletic joggers ($3.99) from Canvas, which paired perfectly with Kaitlyn's black graphic t-shirt and the funky Kalli combat boots we found at Goodwill for $9.99. But, what really makes Kaitlyn's look stand out, is the trendy black-and-white trench coat from Jules & Leopold ($6.99) that gives it just the right touch of casual sophistication. Just like the photos show, Kaitlyn's look is on point for an afternoon in the city!

Jack is ready for a brand new school year with this cool ensemble using designer pieces found at Goodwill! We started the look with a pair of J Crew corduroy pants or $7.99, and we paired them with a navy-blue t-shirt from Zara Man ($3.99), and a ready-for-fall flannel from Land's End for $6.99. The coolest part of Jack's outfit though are the mustard-yellow Undandy designer wing-tip ankle boots we picked up at Retique for $49.99! The boots add just the right pop of color as we head into fall and Jack is ready to hit the books and show off his unique style.