After apple picking and the PSL, nothing says fall quite like a plaid shirt. Like a classic button-down and jeans, this timeless topper holds a place of prestige in almost every closet thanks to its versatility and crazy cozy vibes. But like any basic, it needs an update every once in a while, which is why this week we’re focusing on finding new ways to style the fave piece of lumbersexuals, hipsters and, of course, stylish ladies everywhere. From work week essential to unexpected night-out hero piece, here are three fresh ways to style this tried-and-true top.

How to Style a Plaid Shirt for Work


Workin’ a plaid shirt at the office is an exercise in effortless dressing. Simply swap out your go-to button-down or blouse for this checked number and watch the sartorial possibilities unfold. Strike the right balance of polished and comfy-meets-chic with a leather-look skirt, an oversized knit and chunky heeled ankle boots. A silvery sac makes toting your nine-to-five essentials a snap, and marbled baubles add a hint of of-the-moment flair.

Penfield Jansen Plaid Shirt ($85) + River Island Dark Red Leather-Look Midi Skirt ($30), Mango Mixed Knit Sweater ($40), Vagabond Tyra Boot ($180), Accessorize Classic Bucket Tote Bag ($80), Tourterelle Drops ($48), Patricia Vargas Kali F1 Phone Case ($35), RMS 5-Free Formula Nail Polish ($15)

How to Style a Plaid Shirt for a Night Out


Make your plaid shirt shine bright on a night out with a metallic A-line skirt with a retro edge. To give the topper a fun, festive feel, stick with statement accessories like fluorescent kicks paired with funky sheer socks, tassel earrings and an eye-catching graphic clutch. Give those eyelids a quick swipe of the shimmery stuff and prepare to turn some heads.

Penfield Jansen Plaid Shirt ($85) + Lizzie Fortunato Pick Up Sticks Pouch ($150), Maison Kitsuné A-Line Metallic Mini Skirt ($158), ASOS Performer Pointed High Heels ($99), Bauble Bar Festival Tassel Drops ($32), Laura Mercier Fairy Dust Eye Shimmer ($28), Hansel from Basel Sheer Ivory Dot Socks ($24)

How to Style a Plaid Shirt for the Weekend


Plaid shirts have off-duty written all over them. Go for the ultimate classic combo by pairing them up with on-trend cropped denim and a warm, fuzzy vest with a folkloric twist. Block ankle boots and bright, fringe-flecked earrings cut the outfit’s laid-back vibe, introducing an air of sophistication that’s perfect for everything from brunch with your besties to casual first dates.

Penfield Jansen Plaid Shirt ($85) + Topshop Faux Fur Embroidered Gilet ($140), Dondup Shocking Jean ($198), BDG Mini Leather Tote Bag ($89), Zara Leather Ankle Boots With Block Heel ($139), Radà Earrings With Stones and Ribbon Fringe ($172), Cheap Monday Fuller Round Sunglasses ($36), Dinoplatz Lip Balm ($15)

What pieces in your closet deserve more attention, but stump your style game? Tell us about your trickiest wear-again garments in the comments below and we might feature them in our next Style Resolutions post!