Fashion Experiment: Cropped Flare Jeans!

So, guys, denim is kind of a crazyhouse these days, at least when it comes to trends and what’s coming through the market. High-rise, mid-rise, cropped, long, flare, boyfriend: it’s all out there, it’s all being worn and it’s available at multiple price points and multiple outlets ranging from the mass-market to the high-end. There is something happening when it comes to jeans — I predict the end of the skinny jean hegemony, but I’m not yet sure WHERE it’s going.

But the high-rise cropped flare is emerging as kind of the “fashion-trendest” of them all at this point. (“Trendest” is not “trendiest” — right now I’m not sure what the most fashion-forward way to wear denim is.)

Cropped flares are super-tricky, though — for a lot of people, they are a radical shift in silhouette, after what seems like a lifetime of skinny and super-skinny jegging-type of jeans. They call for a different sense of proportion, different tops, different shoes.

Normally I’m enough of a contrarian to wait it out and stick to my (skinny) guns. But…I actually think cropped flare jeans are super-cute, in a weird goofy way. In a kind of “Man Repeller” way, if you will: they are kind of jejune and gamine and even sexy, but not in the typical accepted bougie way. That, I definitely like! (I like to wonder what ‘quirky-sexy’ looks like.) But I also think they are a nice way to shake things up. Sometimes you have a moment of “Sigh…skinny.”

So when I found a pair of cropped flare jeans with a raw edge hem at Target, I pounced on them. Normally I don’t buy clothes at Target. (Shoes and bags, on the other hand…) And these aren’t the most perfectly-fitting ones: they definitely stretched out like crazy, and I wish they were more snug in the thigh and hip, to make for more of a contrast between the flare and the rest of the jean. If I were to invest in this trend with a higher-quality jean, I’d definitely look for a more streamlined cut in the hip and thigh to better deal with the mama belly factor, as well as buy ones proportioned for a shorty like me — chopping off the crop for a higher hem made them less bell-like. But test-driving a tricky trend is arguably a good time to hit the high-street or mass-market, or search high and low in vintage/thrift stores. (I still have residual fast fashion guilt…but I also don’t have $120+ to buy a pair of non-classic Frame jeans, y’know what I mean?)

And I’ve been wearing them often enough, trying them with different tops, shoes and such in my existing wardrobe, in an attempt to “make it work” without completely revamping my closet. Did I succeed? It’s all in the eye of the beholder, but I sure had a lot of fun.

Respect The Higher Rise

So I tried the cropped flare jeans with all kinds of things: my standard-issue striped Breton tops, buttoned-up oxford shirts, cute little boho-y tanks. But one thing was consistent: you need to respect the higher rise! What does that mean? Reveal the waist in some way: half-tuck your shirt it, tuck it all the way in, wear a cropped top. You need a higher rise to balance out the cropped leg — otherwise, unless you are very tall, thin and perfectly proportioned, you run the risk of looking stumpy. (There’s nothing wrong with stumpiness, but as a Shorty McShorterson, I need all the help I can get!) High-rise waists, I think, are very sexy and individualistic in a cool, interesting way. Of course, you can wear a belt, too, which adds a visual element to draw the eye to the place you want it to go — not an option for me, though. (I find they aggravate the rather touchy skin around my C-section scar…oh, #momfashionproblems!)

Above All: Find the Right Hem

Here’s the most tricky part of this genre of jeans: finding just where exactly to crop the leg. You want it just short enough to look like “I AM DELIBERATELY WEARING CROPPED JEANS!” and not too long where it looks a little hesitant and wishy-washy: “Did I really want to crop these? Are these just a highwater type of situation happening?” When you do something this cray-cray (fashion- and personally-speaking, of course), you want to look very bold and confident and clear. Conventional wisdom is just above the ankle bone, but being an aforementioned Shorty McShorterson, I went a tad higher. BUT: I also cut my jeans before I washed them, and they TOTALLY SHRUNK SO MUCH. So now they are a little too short. People, please do as I say and not as I do: wash your jeans before you cut them! Wah!

Try It With A Flowy, Flou-y Top


I bought these jeans at the tail end of summer, so I first tried them out with a lot of silky nothings of tanks…and I found the look to be nicely relaxed and bohemian. But, true to the advice above, I found myself half-tucking in a lot of the tops, unless they were already cropped. Half-tucking is also an option for those who feel a little self-conscious about their mama bellies (like me!) I think this could make a good evening look going into autumn, with a sharp little jacket over them. Just make sure that waistline shows!

Tomboy Style!


Of course, a nice easy pairing for these jeans was the classic Breton top — a mainstay of my early-period mom uniform. It brings out the devil-may-care jauntiness of this style; you honestly cannot go wrong here, really. And again, half-tucked in, because I am nothing if consistent and lazy at the same time when it comes to clothes.

They Are A Perfect Offset to a Menswear-y Look


This was a fun, fun experiment! I have long been a fan of that kind of Rag and Bone type of ladysuit — you know, jacket, buttoned-up oxford, casual jean. (I once saw makeup artist Gucci Westman wear this kind of outfit, no makeup and a simple bun and believe me when I say it was the height of chic…but of course, she’s married to one of the heads of Rag and Bone!) But it never quite worked on me in the way I quite wanted…just a little too tomboy on my athletic-y yet curvy self. But wearing it with a cropped flare and a daintier, girlier shoe somehow offset the suit-y vibe enough. Which brings me to…

This Is The Perfect Jean to Show Off Your Grooviest Shoes


Yes, you can wear a chic sneaker or a simple ballet flat with a cropped flare, and it will be perfectly charming. But this hem length is really a way to spotlight your most awesome ankle boots, flats and strappy options. Of course, it all depends on your body type, style and fashion temperaments. I personally loved wearing these jeans with ankle boots and lace-up pointy-toed flats, but wearing them with a sneaker, no matter how fashionable, just felt way too sloppy for me, no matter what the top. But of course, some of you out there might find the opposite! The only thing you can do is try and figure out how it feels for you.

And that’s really the ultimate thing here: there are times you want to just feel cozy and secure and put something on that is cute and awesome enough to forget about fashion and get through those mama-heavy days. But there are times when you are up for creativity and experimentation, and sartorially speaking, cropped flare jeans can be loads of fun.

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