Fashion Flashback

Growing up, we had a love-hate relationship with our penny loafers. In first grade, we loved popping in a coin; but by third, we were bored with this quintessential classroom style. Here, a glossy faux croc finish elevates this prep school staple in a way that we can’t resist.SHOP NOW: Marc By Marc Jacobs Loafer, $162

Constantly getting stuck in skinny jeans was one of many pitfalls from our teenage years. Here’s the modern solution: a jean legging with just the right amount of stretch, so you can get them on and off without all that work (or those reproachful looks from mom).SHOP NOW: J Brand Jean, $196

Whoever has the most friendship bracelets has the most friends, right? Thankfully, that's not the case any more. But we still remember this childhood staple fondly and would love to add these chic woven tie-dye styles to our summer wardrobe.SHOP NOW: Juicy Couture Bracelet, $38

Far from the flat patent styles of your youth, this feminine Mary Jane has a gold block heel and a roomy round toe that make it a great choice for work or play (and definitely worth the splurge).SHOP NOW: A.P.C. Shoe, $470

We all used to cover our jean jackets with patches and pins, but today’s lady reaches for a pre-decorated studded style like this to throw over summer sundresses.SHOP NOW: American Eagle Jacket, $50

This pink ribbon headband with zipper trim is totally age-appropriate ... and hits just the right note of cute-meets-cool.SHOP NOW: Joomi NYC Headband, $62

Rompers are everywhere this season, but going out of the house in this style should be reserved for those of us on the younger side of things. Having said that, how adorable is this cherry red one-piece for lounging around the house on laundry day?SHOP NOW: Topshop Playsuit, $44

There are tons of updated jelly sandals out there, but we love these lavender gladiators, with a slight wedge heel, because they actually look city-suitable.SHOP NOW: See By Chloe Sandal, $125

This Mickey Mouse tank can’t help but make you smile. We’d pair it with shorts and sandals for a fun weekend look.SHOP NOW: Forever 21 Tank Top, $15

Meet a stylish new summer carryall — we love this sleek, sorbet-colored backpack with tan leather trim and tassels.SHOP NOW: Dooney & Bourke Backpack, $195

Every little girl loves a bow, but working this item into your adult wardrobe can be tricky. The serious chain on this rose gold necklace offsets the big, flirty bow — for a statement piece that’s the perfect mix of playful and cutting edge.SHOP NOW: Tuleste Market Necklace, $75

When you’re a kid, pleated skirts are synonymous with holiday dress-up or the dreaded school uniform. But for grown-ups, this playful style has a much happier association, thanks to the softer pleats and wildly colorful stripes.SHOP NOW: French Connection Skirt, $98

This adorable tote will remind you of your first crush. And its easy jersey material and shiny gold straps make it a playful weekend pick-me-up.SHOP NOW: Boy Meets Girl Bag, $75

Saddle shoes always make us happy. This classic navy-and-white style will look great with all your summer clothes. Plus, you’ll be able to slip them effortlessly into your fall wardrobe.SHOP NOW: Cole Haan Shoe, $125

Whether you pick the lipstick red, bubblegum pink or lily white, these Lolita shades are guaranteed to make you feel young and flirty again. (They’re also the perfect beach conversation starter.)SHOP NOW: Fred Flare Sunglasses, $11