37 Plus Size Cropped Wide Leg Pants That’ll Make Your Summer To Fall Transition A Breeze

They’re perfect for those not quite hot, not quite cool days.

By: Marie Southard Ospina

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Much of the world has lived in skinny jeans and tightly tapered trousers for the better part of a decade, but fashion is nothing if not cyclical. The flared and super-wide, JNCO Jean-esque cuts of the ’90s have been slowly reentering the market for some time now, and Fall 2017 may be hitting us with the coolest options yet. Finding niche trends like these in extended sizes was once a near-impossible feat, comparable to slaying dragons or landing an invite to the Met Gala. Lucky for us, these 37 plus size wide legged, cropped pants prove that things are evolving for the better.

Dressing in between seasons can often seem complicated at best and garbage-fire-emoting at worst. Cropped and wide-leg pants are just about perfect for the summer to fall transition, though. Their length offers more coverage (and subsequently more warmth) than a summery skirt might, but the flared hems will allow that sweet autumnal breeze to hit your knees when the days are on the warmer side.

Whether your sartorial tendencies err on the side of vintage-inspired, minimalism-heavy, or boss babe-like, there’s undoubtedly a cropped and flared trouser out there to fit your every chic and nuanced need. With some clever layering, you may even be able to rock some of these come the A/W transition, too.


Florals In Fall

Florals are traditionally thought to be summer prints, but there’s no reason not to take them into autumn. The navy hue of these babies will feel more season-appropriate, while the flower detailing keeps things upbeat and whimsical.

Modern Boardroom Babe

Whether you’re working or playing, you’ll look effortlessly cool and professional in these tropical print trousers. Not only are they perfect for that summer to autumn transition, but they’ll get you from the office to the cocktail bar, too.

Retro Details

The retro-inspired suspenders on these guys will make you look like a Mad Menextra with very little effort involved. Although slightly longer in length to many of their counterparts, the trousers are also cropped enough to let you show off your late summer or early autumn mules.

Subtly Nautical

Gold buttons accenting navy trousers make for an effortless sailor babe aesthetic. Pair these with your favorite striped T-shirt and slay all day.

Wear White After Labor Day

You can most definitely wear white after Labor Day, if for no other reason than to rock the hell out of these pants. The eyelet details on the waist make these trousers feel less about long walks on the beach and more about pumpkin spice lattes.

Timeless Beauty

The story goes that every woman and femme needs a little black dress in her wardrobe... but what about the little black pant? These trousers will pair equally nicely with your favorite tee or a more formal button-down, so you can quite literally wear them for any occasion.

Casual Elle Woods

Elle Woods would undoubtedly approve of the color of these pants, perhaps not so much of their slouchy nature. No matter. You know there's no shame in comfort.

All Tied Up

The rope belt on these culottes is so very eye-catching yet so very simple. In fact, the same could be said of the trousers in their entirety. What a catch.

Athleisure Revisited

Sportswear-inspired stripes and cuts were all the rage in 2016. For 2017, why not give the trend a more sophisticated, striking edge? These zipper-detail cropped trousers are just the thing you need to make a memorable entrance.

Flamenco Vibes

The deep clementine hue and ruffle hem of these pants should help you feel flamenco-ready wherever you may be. There’s an unapologetic romance to them that’s sure to catch eyes with every step you take.

For Your ’50s Fancies

How utterly sweet are these gingham culottes? Pants as precious and vintage-inspired as these deserve to be worn trans-seasonally.

Easy & Breezy

The wardrobe staple you never knew you needed, these wide leg crops can easily be dressed up or down. Slip on a chunky knit on cooler days or a Bardot top when the sun is out. They’ll work with anything.

A Little Bit Of Sheer

Pleated and sheer: What’s not to love about these trousers? The temperatures may be starting to drop, but there’s no reason not to stay glamorous.

A Modern Hippie

The wash, rise, and the hem of these capris scream ’70s, which is just how you like it. Now get yourself a tie-dye or embroidered blouse and let everyone know you’re a lover of peace and folk music.

Spooky Chic

You’re a grown-ass woman who still loves that Beetlejuice aesthetic. No shame, babe. These pants are the perfect way to channel your devotion to black and white stripes and creepy films alike.

Soft Denim

The frayed hems and pipe detailing on these cropped denim trousers will ensure you take those light festival vibes with you into the next season.

Forever Love Pink

Ease into early fall with these delightful berry crops. The side slits add just a little sexy into an otherwise minimalist, professional look.

Black On Black

All these black gauchos need is the addition of your favorite black top and you’ll have a bonafide outfit. There’s nothing quite as chic as a black-on-black combo no matter the season.

Picnic Ready

Grab a picnic basket and make the most out of the remaining warm afternoons before winter comes back. These gingham pants could be paired with an embroidered peasant blouse or black button-down and look equally adorable.

The Easiest Denim Around

Get the look of your favorite denim without the fuss. The loose-fitting nature of these lil’ gems means you’ll be forever comfortable without having to tackle buttons or skinny jean fits.

For The Queen B

Something about these cropped palazzo pants screams “Blair Waldorf.” If you’re an aspiring Queen B who dreams of sipping French coffee on the Triangle d’Or someday, trousers like these should offer a more realistic and budget-friendly alternative.

White On White

If you’re of the opinion that every closet needs some white basics as well as black ones, let these denim crops guide you through the fall. These can be rocked with your favorite band tee, a seasonal lace-up knit, or an oversized blouse. Anything goes.

Mom Trousers

You may think of your ’90s mama the second you hear “Eileen Fisher,” but here’s the thing: ’90s moms were quite possibly among the coolest-dressed parents of all time. These organic cotton pants will make you look sophisticated yet approachable.

Rustic Bae

Whether you fancy yourself a Brooklyn hipster or a rustic country babe, these brown trousers will have you covered. You’ll even complement the changing leaves as you walk past some trees. Who wouldn’t want that?

Modern Art

There’s no way these culottes won't call to mind images of paint-speckled modern art. Wear them with pride.

Babe On The Town

You’re hot AF and you know it—and so are these trousers. The bow-tie waist is just the kind of pop you need to make a statement without looking like you actually tried.

Elegant Flares

If natural fibers and subtle flare detailing sound like your jam, Eileen Fisher will have you covered. These pants are 100 percent organic and 100 percent fancy.


You’re a strong, powerful woman and your love of lace does not negate this truth. Even so, you could rock these trousers with a sturdy pair of mules or Oxford flats if you want to keep things a little more modern.

Elevated Sweats

Who says you can’t wear sweatpants out of the house? These capris are as comfortable as your old workout pants, but a little more grownup.

Totally Artsy

No one will doubt that you’re a creative soul when you’re rocking these glorious trousers. They are just that artsy and casual.

Understated Stripes

Chunky stripes are certainly not the only kind of stripes that make a statement. The understated lines of these trousers are subtle, striking, and oh-so-sophisticated.

Small Daisies

Look closely and you’ll see tiny daisies decorating these soft jersey culottes. They’re absolutely charming.


These culottes are bananas, in the best way possible. Take some summer vibes with you through this seasonal transition, because looking at these would make anyone happy.

Polka Dots For Days

Polka dots are among the most classic prints of all time, and these trousers prove it. They are ever-so-slightly reminiscent of vintage ’50s prints, but with an irrevocable contemporary feel.

Candy Striper

These pants give off major candy cane vibes without the added sugar rush. You’ll still look sweet AF, though.

With A Bark

The color of these pants is called “bark,” and they certainly do. The one-of-a-kind hue is unique, thus elevating the otherwise simple trousers into legendary high-fashion status.

Take Up Space

The color! The cut! The fabric! In these wide-leg trousers, you will take up space and be seen—which is just the way you like it.

The transition from late summer into early autumn is a glorious time of year. Thanks to this assortment of wide-legged, cropped pants, your style will be just as glorious, too.


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