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In this very special edition of 5 Days, 5 Ways, we take on an all-season trend many of us non-model-size individuals dare not attempt: fashion-friendly overalls!

Here's the problem with these coveralls: Oftentimes you need legs for days to avoid any frump factor. (The oompa loompa look? We think not.) Not to mention, styling these pieces can easily veer left into farmer Jane territory.

So how do we master this trend so beloved by stylish stars like Zendaya and Taylor Swift? We turned to E! Style Collective stylist Lindsay Albanese for help. Watch her break down five street-style-worthy looks inspired by our favorite celebs in video above.

ESC, Overalls 5 Ways

The ‘70s are back with a vengeance, and this is no more apparent than with the flared leg trend. Overalls are tricky enough for shorter ladies (this writer included!), but add wide-legs and we definitely need some assistance to take our look to new heights. "Wear a heel or platform and make sure the hem hits a hair above the floor to maximize your length," Lindsay suggested.

American Apparel crop top; T.J.Maxx overalls; Steve Madden shoes; Madewell bag

ESC, Overalls 5 Ways

Overall shorts can be a throwback to your elementary school days...or you can channel your inner tomboy (like Ashley Tisdale) and pair them with a polished oversized bag, sneakers and a tied flannel around your waist for that casual-cool vibe. Pro tip: "If you're concerned about exposing your thighs, choose styles that give you ample room in that area to create the illusion of slimmer thighs," she advised.

Monrow T-shirt; LuLu's overalls; New Balance shoes; Vita Fede bracelet

ESC, Overalls 5 Ways

The denim-on-denim trend is all the rage right now, as evidenced by It Girl Zendaya. But try the look using two vastly different washes and don't forget the statement shoes for a mix-and-match effect.

Rails top; Black Orchid overalls; Steve Madden shoes, Flynn bag, DANNIJO necklace; Vita Fede bracelets

ESC, Overalls 5 Ways

No one throws together a surprising-but-polished look better than Olivia Palermo , who paired a leather one-piece with an off-the-shoulder top. "The combo gives the look a lot of detail and impact," said Lindsay. "It's adventurous and dramatic. We're showing a little shoulder while there is added texture with the faux leather."

Line & Dot top; Whitney Eve overalls; Charlotte Olympia shoes; MCM clutch

ESC, Overalls 5 Ways

Leave it to Tay-Tay to show us how to prep up overalls. Not only did she opt for a tapered, fitted pair, but she complemented her black iteration with classy shoes. "Try loafers for summer or pointed oxfords, which gives it a fresh look and isn't so typical," Lindsay suggested.

Vintage scarf; Michael Stars tank; Cheap Monday overalls; Minna Parikka shoes; MCM bag