One of the hottest fashion trends today is sure to conjure up memories of the early 2000s. Cropped pants are back and better than ever, and we love that they can be dressed up or down to create a super-stylish and comfortable outfit, perfect for fall’s transitional weather. Today, we are demonstrating three different ways to wear cropped pants in hopes of inspiring you to embrace this old-school trend! Be sure to let us know in the comments which look is your favorite and how you’d style cropped pants.

Dôen Top // Everlane Pants // Clare V. Bag // Freda Salvador Shoes (on sale!)

How Taylor Styles Cropped Pants:

I’ve wanted to try wearing cropped pants for ages now, but I’ve always been worried that I am too short to pull off this trend. I knew Everlane’s cropped pants would be a great way to try out this trend because of the brand’s attention to detail and impeccable design. I have to say, I love the fit and they are the most comfortable pants I own! I styled them with clothing and accessories from small business brands that I love. The cropped blouse by Dôen works nicely with the high-waisted style.

CAMI NYC Racer Top / Black Mules (similar, on sale!) / Everlane Pants / White + Warren Travel Wrap / Ray Ban Classic Aviator

How Annie Styles Cropped Pants:

I’ve been loving this pant style all summer long, and I’m excited to wear them this fall, as well. Most of the time, you’ll find me dressed in neutral staple pieces, and these pants have definitely earned their spot as a staple. Because it will stay fairly warm in Nashville for a while, I paired the pants with a black silk cami to stay cool and a cashmere wrap for a fall look and feel.

Zara Tank (similar) // Zara Kimono (similar) // Everlane Pants // Urban Outfitters Loafers (similar and only $9!) // Vintage Bag (alternative and under $100) // Le Specs Sunglasses

How Abby Styles Cropped Pants:

I typically stick to skinny jeans, but I am always down to try out and experiment with new styles. I was super excited to try out the cropped wide-legged trend because I’ve seen it look so good on other people. However, I was also nervous because I’m a little shorter and have curvy hips. I’m happy to say that I was pleasantly surprised with how well they fit—and how comfortable they were to wear. Since living in SoCal and working from home, my day-to-day style is pretty relaxed. I’ve been wearing this kimono on repeat for awhile and it is the perfect traditional piece to wear as we go into fall because the colors look really rich with reds and purple. Since the cut of the pant and the kimono make a pretty big statement on their own, I decided to keep the rest of the look pretty simple. I’ve had these velvet smoking shoes forever and I love to bring them out each fall. I added one of my favorite vintage bags and sunglasses to complete the look.