Jeans! The ultimate wardrobe staple is also, somehow, one of the most complicated pieces of clothing to shop for. Fit, proportion, and overall “feeling yourself”-ness all need to be perfect. And once you find your style, it’s scary to dip a toe into a new trend—even if everyone else makes it look so effortless on Instagram. We hear you, we got you. Welcome to your fall denim styles guide. These slight tweaks to your old reliables will not only expand your denim vocabulary, but, we promise, make you excited to wear a new pair. Especially once you see how to execute the look jean-iusly (sorry, had to) for day, play, and when you're off-duty.

Love Boyfriend? Try Baggy

Claudia Li top, Mother jeans, Jenny Bird earrings, Chanel belt, Sergio Rossi shoes, Balenciaga bag.

This style takes boyfriend cut up a notch with a more dramatic width and length. Seemingly unpolished, the heaviness of the baggy cut actually holds its own as a fashion-forward silhouette that demands attention when paired with an equally bold top.

Love Flares? Try Side Splits

Nanushka top, 3x1 jeans, Sarah Chloe ring, Tabitha Simmons shoes, Sezane bag.

A hybrid that brings the slimming power of a skinny and the fun of a The Side Split! With a very literal split up the side of the outside or inside seam, she’s carefree and kind of gossipy, revealing just enough to make her a perfect brunch/drinks/coffee break companion, down for any occasion.

Love Skinnies? Try Straight

Stine Goya sweater vest, Dior turtleneck, Re/Done jeans, Marc Fisher boots, Celine by Hedi Slimane bag, Sézane bracelet.

The skinny jean has been mainstream now for nearly 15 years and there's no reason to believe the style will be disappearing anytime soon. But there is something freeing about giving your ankles a little bit of breathing room courtesy of the skinny's equally flattering sister, straight-cut. This is the quintessential jean style that transcends decades and fads. Adding it to your wardrobe this season is a no-brainer.

Love Wide-Legged? Try Trousers

Dior blazer, Theory top, Goldsign jeans, Pascale Monvoisin necklace, Roger Vivier shoes, Boss bag.

If you love “wearing the pants” (i.e. the in-charge feeling a wide leg jean gives you), then get even bossier with trouser jeans. The long line and clean front pleating of this style is a done deal for daytime, but also has a softer side, seamlessly transitioning to happy hour and the dog park.

Fashion Editor Julia Gall / Hair by Takashi Yusa / Makeup by Michela Wariebi for Nars / Models, Jordan Moon at Muse NYC and Adesola at One Management / Casting & Production by Suze Lee / Special Thanks to Peerspace

Lead image from left to right: Ganni top, 3x1 jeans, Staud boots, Gucci belt, Hunting Season bag; Khaite cardigan, Mother jeans, Washed Ashore necklace, Loeffler Randall bag; Miu Miu sweater, Re/Done jeans, Vionic shoes, Elizabeth Locke earrings; Brock top, Goldsign jeans, Stuart Weitzman shoes, Ippolita earrings and bangle.