Is This Weird New Fashion Trend Right For You?

Where do you fall on the pants spectrum?

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Skinny Jeans Are the Cruel Corset of the 21st Century

Chantal Strasburger, assistant editor, @chantagold

The best part about wearing overalls is that I never have to worry that my fly is undone.
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Let's play a quick game of word association. When I say "sweatpants," you say: _____. When I say "elastic waistband," you say: _____. When I say "overalls," you say: ______. If you filled in the blanks with some variation of cozy/comfy/easy, you're my kind of person.

Don't get me wrong—I love zippers and buttons and laces as much as the next clothing-obsessed person. But when it comes to pants, the easier they are to slip on (and the less restrictive they feel), the more likely I am to wear them.

Elastic-waist pants (and office bathroom selfies) for the win.
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I wasn't born with this perspective. It took years of squeezing myself into skinny jeans and trying to convince myself that low-rise cuts work for my body type (they don't) to discover the world of stretchy pants and mom jeans.

Just because pants are comfortable doesn't necessarily mean they're unflattering.

Before we continue, let me set one thing straight: Just because pants are comfortable doesn't necessarily mean they're unflattering. Yes, I have a few pairs I wouldn't exactly wear on a first date, but there are plenty of designs that make you look good while allowing you to feel good, too.

An easy, breezy pantsuit (I really like pantsuits, OK?).
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Not quite sure where you fall on the pants spectrum? Check out your local thrift store and try on a few styles—that's where my introduction to comfortable pants took place. Looking for some cheap jeans in college, I stumbled across an incredible pair of patterned pants with a forgiving waistband from the '80s, and they turned out to be my gateway drug to relaxed denim and no-fuss overalls.

Moral of the story: Don't sacrifice comfort for style, and vice versa. For every pair of pants that force you to wiggle your way in, there's an equally fabulous option with zero sucking-in required.

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Satin Pull-On Trousers, $68, us.topshop.com.

Printed Loose Fit Pajama Bottoms, $70, zara.com.

Cotton Joggers, $35, hm.com.

In Praise of Difficult Pants

Caitlin Petreycik, senior fashion editor, @c_petreycik

Everlane's wide-leg crop pants are already back-ordered. Photograph courtesy of Everlane
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Sometimes, it takes a little while for our eyes to adjust to new silhouettes, and longer still to actually try them. A few seasons ago, off-the-shoulder tops and giant bell sleeves didn't look quite right; they were too Oktoberfest (the former), too Medieval Times (the latter), too...fussy (both). Fast-forward and here we are, applying sunscreen to our shoulders and accidentally dunking our enormous sleeve cuffs in queso.

Let cropped, wide-leg jeans be your gateway purchase to cropped, wide-leg *pants*. Photograph courtesy Gilbert Carrasquillo/GC Images

Now that designers have pushed tops to their limits, they've turned their attention to (non-denim, non-drawstring) pants. Specifically, slit-front trousers, kick flares, and, in my opinion, the easiest to wear: cropped, wide-leg sailor pants. They're unexpected, slightly '70s, and bridge the gap between dressed up and laid-back. Basically, you can go to a fancy-ish party, duck out early, eat a slice of pizza on a park bench, and not look out of place once the entire night.

The Wide-Leg Crop Pant, $68, everlane.com.

Jesse Kamm's wildly popular cotton canvas sailor pants have been dominating Instagram for a while, and Everlane just released a $68 denim version of the trend (I've worn them and they're comfortable and stretchy, although they run a bit big).

I think the pants' "difficult" reputation comes from the fact that they just don't give good dressing room. Try them on with an oversize shirt and that high waist is lost; add too-chunky shoes and an ankle-length hem looks like an accident.

The Wide-Leg Crop Pant, $68, everlane.com.

Here are some things that do look amazing with cropped, wide-leg sailor pants: bodysuits, plain white T-shirts (tucked in), mules, low block heels, and sleek ankle boots. Arm yourself with those items, be prepared to have your new pants altered if necessary (length is key here, and most tailors will charge $10 to $15 to shorten a hem), and pat yourself on the back for being an early adopter of statement pants. They're only going to get weirder from here.

Sailor Pant in Olive by Jesse Kamm, $395, needsupply.com.

Long-Sleeve Keyhole Body, $38, topshop.com.

Villa Heels, $325, loq.us.

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