Jess’ Take on Cropped Denim: High Waisted, Straight Leg FTW!



Oh happy day! You guys, we’re almost to the end of Crapped (ha! typo but it’s staying) Denim Week here at TME. We learned a lot this week, mainly that a few of you have some REALLY strong feelings about cropped denim. We get it, because we were once skeptical, too. 

But I’ve been thinking…we’ve been talking all week long about cropped denim and we’ve never once stopped to acknowledged the style icon who’s bold choice of trousers paved the way for the rest of us and made our cropped denim dreams into reality:



So… if you only take one thing with you from this week, please let it be that Steve Urkel is to thank (or blame).

Like everyone else, I had some major concerns right off the bat, mainly that they would make me look shorter and bulkier. I’m 5ft 7” but with wide hips and “ athletic” (aka meaty) legs, so I was worried cropped jeans would do the opposite of what I am always trying to accomplish, and make me shorter and wider.  I ordered several pairs and heres what I found…..

For my body type, a straighter-leg hem was the clear winner.  If you are tall and skinny with legs that never end (cough, cough *cam*) then you can wear those flares with abandon.  But for me, a high-waisted and a straighter crop helped to lengthen my frame.   Also, my budget for a pair was under $100.

I tried all sorts of style combinations and unlike my usual loud and complicated self,  this time I preferred the simplest look: a black turtleneck and loafers and/or ankle boots.

With Oxfords…




With heeled booties….





Outfit Details:

Top – I’ve invested in TWO black turtlenecks recently. The first is Free People’s Modern Cuff Turtleneck, $40.99, (runs large so order down), a thin, lightweight version I can wear under a lace cami (which is like my favorite thing to do at the moment) and also so I can tuck in my shirt without worrying about extra bulk. The second is a Style & Co ribbed knit turtleneck, currently 50% off at $24.99, a price too good I couldn’t pass it up.

Jeans –  Topshop’s Busted Knee Straight Leg Jeans, $85.99, was the clear winner for what I was looking for.  For a GOOD quality pair of jeans under $100,  UK boutiques Topshop and River Island have that market on lock. The quality of the denim is great and is crafted with 1% elastine so I can eat that second donut.

Shoes – One of the few pairs of shoes I’ve worn consistently through the last 4-5 years are my KMB Cutout Oxfords, $128.00. Easy to slip on and off and super comfortable,  they are some of the most well worn shoes I own. The black ankle booties, are very similar to Sole Society’s Lyric Booties and as you can tell from all the scuffs, they’re another well worn and well loved pairs of shoes.



P.S.  I DIY-ed myself a pair using some old jeans and ended up really liking the result!


I gave them a high-low frayed hem by taking off an extra 1.5″ in the front, so that they’re longer in the back. That’s always an option for anyone not completely sick of cropped jeans already.


Thanks for sticking with me to the end! We’ll be returning to our regularly scheduled broadcasting soon. Follow me on instagram @jessbobess for more shenanigans!






  1. Yep. It’s the flare that killed it for the others. The crop looks good, especially with the booties. And the high waist makes you look curvalicious! But cropped AND flared is just bad bad bad.
    You look great! I’m glad you stuck to your guns and didn’t do the flare just for the sake of doing the trend, but I do love seeing the fails! It would have been good to see a side by side.

  2. I like the ones you did yourself better! Seems like starting with a pair of jeans you like might be the key. Too bad I donated all my boot leg jeans…

  3. So next up… mom jeans? Ha! Ironic with the old name. Anyway, I’ve been intrigued by the “mom” jeans (high waisted tapered leg), they seem more flattering than cropped flares, I think? I’ve seen pairs at ASOS and Topshop, and the super hip London youtubers I follow are wearing thing, seems worth a shot.

  4. Ok, I haven’t chimed in yet…I’m 5’8 with a 33″ inseam and I have LOVED my cropped flares from the very first pair I ordered…Maybe it was a lucky shot? (Citizens Fleetwood High Rise Cropped Flares in Icon). I can pretty much wear them with anything in my wardrobe and feel good. The only problem is having to shave my legs (at least part way) whenever I want to wear them! Also, I’m kinda worried about the cold ankle come winter. :/

  5. Great job!! This trend wasnt exactly your style but you jumped in and nailed it!! Kuddos for making the look yours and knowing your body and making the trend work for you. I LOVE the high waisted stair-step crops and finally flats that actually look cute with crops. But still would have loved to see your rendition of the cropped flares for cropped flares week even if the final decision was a hard NO pointing/highlighting as to why this look was better for you. Those comparisions (with pics) really help us nail down what works for our body and why. Love your simple look. Shana can we please please get a take away run down/summary on what worked and why and what was a hard no and why. Nice job TME!!

  6. These work!!! You win Cropped Flares Week!! I guess you cheated a little bit by choosing a straight leg over a true flare, but does it matter when you look so darn cute? Nice work.

Leave a Reply