Sailor Pants (AKA Cropped Trousers) Look Effortlessly Chic With *Everything*—These Are the 9 Best Styles To Wear This Fall

As the temperatures start to dip and we creep closer (and closer) to fall, you may be on the hunt for new pants to take the place of your summer shorts and skirts. While it might be tempting to reach for a pair of jeans or black leggings, we say nix the basics—it’s high time to stock up on sailor pants. The cropped, classic trousers best defined by their high-waisted, wide-legged silhouettes look effortlessly chic with everything. And we mean everything; A sweater and boots, a cropped tee and sneakers, a lacy tank and some mules, even slippers—these cute culottes are as versatile as they come and are the most comfortable way to look put together in a pinch.

The best sailor pants, at a glance:

• Best overall: Rolla’s, Sailor Jeans, $109-$149
• Best budget: SweatyRocks, High Waist Double-Breasted Wide Leg Pants, $38
• Best splurge: Askk NY, Sailor Pant Mulholland, $299
• Most sustainable: Duer, Luxtwill High Rise Trouser, $139
• Best linen: Maeve, Colette Cropped Wide-Leg Pants, $120
• Best retro: Frame, Sailor Snap High-Rise Wide-Leg Jeans, $288
• Most comfortable: Spanx, On-the-Go Wide Leg Pant, $138
• Best full-length: Boden, Sailor Wide Leg Jeans, $130
• Best minimalist: Everlane, The Way-High Sailor Jean, $128

What are sailor pants?

As you can probably glean, sailor pants have a nautical history. They’re named for the flared, high-waisted trousers worn by 19th- and 20th-century sailors. Some sources claim the bell bottoms were easier to roll up while cleaning the deck, while others report the flared legs were precautionary, and would ensure sailors could easily get out of them without having to unlace their shoes if they fell overboard into the ocean.

Generally, today’s sailor pants sport the same features in more modern designs. Oftentimes, they feature ankle-skimming hems while other times they’re longer, for a fuller bell-bottom appearance. No matter the inseam, color, or design, they’re universally flattering and look chic with any outfit. To prove it, find the best sailor pants below, guaranteed to give you smooth sailing, er, styling, through fall and beyond.

The best sailor pants for women

Best overall:

Rolla’s, Sailor Jeans — $110.00

Available sizes: 24-32

Say “ahoy” to the Rolla’s Sailor Jeans, which are some of the most versatile on the market. Sold in 16 (!) different colors and washes, the slightly stretchy cotton denim pants hit just above the ankle, feature front and back patch pockets, and showcase thick statement seams at the hem. Prices vary by wash. 

Colors: 16

Inseam: 28.5” 

Pros: 

• 16+ washes
• Inclusive size range
• Slightly stretchy
• Made with sustainable materials

Cons: 

• Sizing is inconsistent and varies on wash

Best budget:

Amazon - SweatyRocks, High Waist Double-Breasted Wide Leg Pants — $38.00

Available sizes: XS-XL

For a dressier take on sailor pants on a budget, consider this pair from Amazon. Sold in 11 different colors, the thick jersey pants look like high-end trousers but feel like luxurious sweats. As such, they work well for the office and weekend brunches alike. 

Colors: 11

Inseam: N/a

Pros: 

• 11 different colors
• Stretchy
• Affordable

Cons: 

• No sustainable materials
• Lightly lined—might show underwear lines

Best splurge:

Askk NY, Sailor Pant Mulholland — $299.00

Sizes available: 22 to 34

The Askk NY Mulholland Sailor Pant looks lived-in but feels luxe. The high-rise, wide-leg pants feature distressed accents and even a few paint splatters to give them an artistic flair. A word to the wise: The brand suggests not tossing them in the dryer, so make sure to hang them to dry.

Colors: 1 

Inseam: 30” 

Pros: 

• Inclusive size range
• Slightly stretchy, lived-in feel
• Made from sustainable materials

Cons: 

• Expensive
• Only one wash

Most sustainable:

Duer, Luxtwill High Rise Trouser — $139.00

Available sizes: 24-34 in two inseams

If sustainability is your top priority, get these Duer trousers. Everything the brand makes uses recycled and sustainable materials that are better for you and the planet. That includes these stylish trousers, which are made from 98-percent organic cotton that is so soft. Like, so soft, you’ll forget you’re wearing hard pants in the first place. A smidge of elastane in the blend makes them stretchy, too, so you can wear them all day with ease. The pretty autumnal palette, like copper red and thyme greige don’t hurt, either.

Colors: 3

Inseam: 26″-28″

Pros: 

• Inclusive size range and two inseams
• Slightly stretchy
• Soft twill fabric
• Made with sustainable materials

Cons: 

• Pricey

Best linen:

Maeve, Colette Cropped Wide-Leg Pants — $120.00

Available sizes: 24-34 in standard, tall, and petite inseams and plus sizes

For more of a column sailor-y silhouette, check out the Maeve Colette Cropped Wide-Leg Pants. Made of soft, breathable, ever-so-slightly-stretchy linen, these lightweight bottoms are the perfect transitional pant, great for the inevitable warm fall days that refuse to cool down. And the Medium Pink color? Barbie would approve. 

Colors: 10 

Inseam: 24”-29” 

Pros: 

• 10 different colors
• Inclusive size range with tall and petite inseams
• Slightly stretchy
• Lightweight and breathable
• Made with sustainable materials

Cons: 

• Pricey

Best retro:

Frame, Sailor Snap High-Rise Wide-Leg Jeans — $288.00

Available sizes: 23-34

We love the Frame Sailor Snap High-Rise Wide-Leg Jeans because they’re one of the few pairs of denim that feature columns of buttons as opposed to front patch pockets. As suck, they’re a dressier form of denim that could just as easily be styled for a morning at the Farmer’s Market as they could an afternoon in the boardroom. Just keep in mind, these pants are super long so you may need to hem them if you’re on the shorter side. 

Colors: 1

Inseam: 34” 

Pros: 

• Inclusive size range
• Slightly stretchy
• Vintage aesthetic
• Made with sustainable materials

Cons: 

• Only one wash
• Expensive
• Runs long

Most comfortable:

Spanx, On-the-Go Wide Leg Pant — $138.00

Available sizes: XS-3X, in regular, petite, and tall

If you’re looking for a comfortable “do-everything” pant, look no further than the Spanx On-the-Go Wide Leg Pant. They’re a dream to wear and are pretty much the leggings of sailor pants. And they’re super sculpting, featuring the brand’s signature hidden core-shaping technology combined with four-way stretch for maximum comfort. 

Colors: 3 

Inseam: 23.5”-28.5” 

Pros: 

• Wide size range with petite and tall inseams
• Stretchy and sculpting
• No zippers or buttons
• Versatile

Cons: 

• Only two colors
• Not as sustainable as other options

Best full-length:

Boden, Sailor Wide Leg Jeans — $130.00

Sizes available: 2-22, in regular and petite inseams

Want a full-length fit? The Boden Sailor Wide Leg Jeans look more like chinos and are sold in tan and dusty rose hues that will work beautifully for fall. Rather than patch pockets, they’re accented with tortoiseshell buttons on either side of the fly. 

Colors: 2

Inseam: 29”-31”

Pros: 

• Inclusive size range with two inseams
• Full-length coverage
• Unique tortoiseshell buttons
• Made with sustainable materials

Pros: 

• Only two colors
• Pricey

Best minimalist:

Everlane, The Way-High® Sailor Jean — $128.00

Sizes available: 23-33 in two inseams

If you love the ankle-skimming, wide-leg characteristics of sailor jeans but want to stick to your classic pockets, sans front panel buttons, check out the Everlane The Way-High Sailor Jean. The high-waisted silhouette is minimalist and flattering and works well with cropped tank tops, vintage tees, and boxy sweats alike. 

Colors: 5

Inseam: 27.5″-29.5” 

Pros: 

• 5 different washes
• Inclusive size range and two inseams
• Slightly stretchy
• Made with sustainable materials

Cons: 

• Pricey