Influencer Jenn McNaughton identifies and interprets fashion trends and inspirations of the moment, with a nod to where they’re coming from and how to make them your own.

For every great ‘90s trend, there’s about 10 dreadful. Sure, plaid continues to be draped around the waists of youth and a patent-berry lip has us reminiscing of J.Lo in Selena in the “impersonator during girls night” kind of way. But as much as we adore our “slept-in” kohl liner (aka fast five-minute beauty) and Jennifer Fisher knot chokers, how is one to know what’s appropriate or simply outdated? Because even though Kylie Jenner once wore jelly sandals, doesn’t mean you have to…really.

But with Taylor Swift’s newly revamped look courtesy of Anna Wintour herself, plaid and giant safety pins may soon be re-unified. Without further adieu, I’m deciphering the best and worst of the decade to ensure no reader of The Co. is coerced as the next subject of a What Not To Wear-remake.

flatforms trend

Flatforms:

They’ve got to go. End of story. Whether they’re in sandal or boot form, they look like giant bricks and are incredibly unflattering—even if that’s your intended look. Unless you’re in a Spice Girls tribute band, you get no excuses. Doc Martens will do you fine and will enlist a similar “punk-rock, go-go girl” vibe.

vans trend

Vans:

Okay, if we’re talking the white and pink logo-tee as seen on Rachel in Friends, you can forget it. Too-small t-shirts that look like they could fit your youngest child (physically or theoretically), are a no-go. But if you’ve invested in the old skool kind that go on your feet, then a collective “yaaas” would be appropriate. Bonus points if they’re all-white leather.

candy wrapper clutch

Candy wrapper handbag:

The trend I feel is coming but I wish wouldn’t. Remember those origami-like clutches, handmade out of starburst wrappers? The only question is, who will get to it first? Jeremy Scott or Moschino? Just remember not all of us can pull of Chiara Ferragni’s every sartorial move.

patches trend

Patches:

At first, you may think “the more the merrier”—but ponder that for a long while. Here’s what I’m proposing: think of them in similar fashion to the way you pick friends in your late twenties. You don’t invite just anyone over (at least not in the way you would acquire kids like minions to your lunch table in middle school). Instead, you search high and low for those special gems and keep contacts in your phone to a minimum. Apply this while scrummaging vintage stalls for those denim collectables.

choker trend

Chokers:

Snakeskin, velvet, suede, ribbon—you name it. They’re like collectable beanie babies for me; some DIY’d, others bought for far too much money (Balmain, I’m looking at you). Heck, even a shoelace would do. As long as they didn’t come in a $5 “surprise bag” from Ardene’s, bets are you’ll look chic af.

square toe trend

Square-Toed Boots:

Coming from a girl who swore she was a pointed-toe wearer, exclusively, the square toe is here to stay. Tip: go for a thin, stiletto heel to avoid the chunky “grunge” boot silhouette. We’re going for coven leader, not a former Kurt Cobain groupie.

plaid trend

Plaid:

Only if it’s Marc Jacobs. Flannels can be recycled as park/festival blankets.