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10 Best Transitional Jean Shorts for Early Fall, Starting at Only $33

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Summer might be winding down, but that doesn’t mean cool weather will rush in. That means you will still need a pair of the best jeans shorts for early fall. These pairs help make you feel together on days when it feels like fall in the chilly mornings and summer in the afternoons.

Related: 17 Flattering Jean Shorts to Sport Until the Summer Season Ends

The best pairs of jean shorts come in many different washes and styles; that’s why we curated a list of the best picks for early fall. You want to start by seeking a pair of denim that pairs nicely with tops you can layer and throw on a sweater with. We found high-rise fits, relaxed Bermuda shorts and more for every style and budget ahead.

The Best Jean Shorts for Early Fall

  • Ripped Denim Shorts: Looking for a pair of denim shorts that offer a ripped look without too many tears? This pair from Amazon gives you a happy medium and comfortable light that’s flattering on all figures — $33 at Amazon!
  • A Classic High Rise Shorts: Everlane’s The Cheeky Jean Short have a soft composition, made from 100% organic cotton. The shorts have a high rise and straight legs that isn’t tight around the thighs — $68 at Everlane!
  • Stretchy Shorts: Madewell offers some of the best pairs of denim, and the Pull-On Paper Bag Shorts in bunten wash are no exception. They feature a pull-on paper bag waistband and oversized pockets, made with 100 percent cotton denim with zero stretch. The stretchy waistband and fabric make the shorts so comfortable to live in — $50 (originally $65) at Madewell!
  • Shorts Made for Cozy Layers: If you’re already planning to throw on your favorite sweatshirts and button-down tops, make sure you grab the 4″ Low Stride Shorts from Gap. We love the shorts’ raw hems and casual, relaxed fit — $45 (originally $60) at Gap!
  • A Pull-On Design: The Spanx Stretch Twill Shorts are available in six colors, perfect for early fall days. These have a pull-on design, four-way stretch and functional front and back pocket — $39 (originally $78)
  • A Preppy Pair of Denim: If you’re on the hunt for a casual and comfortable pair of jean shorts for fall, make sure to add them to your wardrobe. The shorts from J.Crew are crafted with “100 percent cotton fabric, aka no stretch, gives which his pair a bit more weightiness,” the brand says. They also boast a mid-rise length and a totally laid-back fit that you can style with a cropped shirt on warm days or a tank top and blazer when it’s cool out — $90 at J. Crew!
  • A Splurge Worth the Money: Agolde’s Parker Distressed Denim Shorts are praised for their exceptional fit and lasting durability. And while they’re pricey, they’re one of the best pair of jean shorts to purchase. The premium non-stretch denim includes vintage touches and cool raw-edge hems. We love styling ours with loafers or sneakers for early fall weather — $148 at Nordstrom!
  • Darker Wash Jean Shorts: Fall is a chance to lean into darker washes of denim, like this pair of jean shorts from Z Supply. They have a jet black wash that looks perfect with a rich red sweatshirt — $69 at Z Supply!
  • Classic Bermuda Shorts: Some days you just want to put on a stylish pair of relaxed shorts. That’s where these Bermuda shorts come in. Equipped with a longer length, these jean shorts don’t lack any character — $55 (originally $70) at Gap!
  • Flirty Roll Cuff Denim Shorts: Free People’s Danni Roll Cuff Denim Shorts elevate any off-duty outfit. These affordable ones have an oversized waist that looks elegant with a brown belt and a loose cardigan — $59 (originally $78) at Nordstrom!

Related: Not Too Long, Not Too Short! These Levi's Denim Shorts Are Up to 58% Off

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