Reader Question:
Screen Shot 2011-10-02 at 4.44.28 PM How would you style cropped cargo pants into fall?  I've been wearing the heck out of a pair of olive cropped cargo pants  this summer. They were from Hot Mama in the spring, and no pics available anymore on their site, but they look sort of like Joie's Generette Pant (pictured).
Over the summer, these pants have been a staple of my "momiform," work mainly with a black or a green J crew tank top and some black flat sandals with little leather flowers to girlie up this otherwise somewhat tough look. 
Here in Minneapolis there's a chill in the air already, and a girl needs a bit more coverage for the morning coffee/playground/grocery stroll.
My favorite shoe for fall – the lace up combat-ish boot – comes off as too literal with the army green cargoes. Sneaks with socks seem a bit dowdy, and there is too much fabric at the legs to tuck into my favorite knee high motorcycle boots without looking like a member of a WW2 German motorbike brigade.
But, these pants are comfortable, washable, and crazy flattering. How would you style them to get another couple months of wear?
– Abby in Minneapolis


Abby – great question!  This is a tricky styling situation!  As you mentioned, these pants are too wide for tucking into boots….and the weather is too cold to go without socks.  (Which I mention only because these pants would look adorable with ballet flats, oxfords or loafers sans socks.  Of course.) 

So.  You want to wear these pants, into the Fall, with warm footwear options.  Gotcha.

Now, I don't have a pair of pants exactly like these, but for this tricky styling situation, I didn't want to rely on a Polyvore collage.  So I "spoofed" your pants by rolling up a slouchy pair of straight-leg khakis.  The color obviously, is different, but I think the overall effect is the same.  Here's what worked for me:

Short Booties

If the combat boot is too literal, you could try a short bootie. It's just as cool, without the military feel.  The small (yet comfortable) heel helps keep the look feminine.  


(wearing: Gap straight leg khakis, Banana Republic silk tee, Daughters of the Liberation sweatshirt jacket from Anthropologie, unknown scarf, Smartwool cable socks, Clarks booties)

Sock color – there are a couple of options.  You can always match the socks to either the pants or to the shoe…but I'm loving the look of socks peeking out.  So I choose a contrasting color that would stand out.

This visible sock idea would also work with ballet flats, oxfords, loafers, etc.  My favorite layering socks are from either Madewell or Smartwool's Cable Knit socks.

Duck Boots

Because duck boots are so preppy, I think they'd provide a cool balance with a some military inspired cargos.  Not to mention that this is the most practical choice, especially for cruddy weather.  I do love my duck boots. Wore these babies all winter last year.


 (wearing: Gap turtleneck sweater and khakis, Lands' End Duck Boots)

Slide Tall Boots Under….

If you have a pair of tall boots that are slim, you might be able to slide them underneath your cargos…and just roll the cargos just a touch.  This look can get very Dickensonian, though, so watch what tops you pair with it.  Personally, I'd avoid ye olde time waiste-coats and cravats.


(wearing: On S – Gap khakis, J. Crew cotton moto sweater, Free People crinkle tunic tank, Biviel tall wedge boots…..on P – Imps & Elves striped pants, Target long sleeve tee)

So that's what worked for me…but our readers are always full of fabulous ideas.  Readers!!  Do any of you have pants like Abby's?  How do you wear them in cold weather?

Thanks for writing in, Abby!




  1. i’m surfing around and happened to notice refinery29 Chicago had a street style picture of a woman wearing army green pants with black combat boots, oxford, blazer and scarf. doesn’t look over the top military. posted 10/13 if you want to look.
    love this site

  2. Thanks for posting this! I have a pair of black pants with the same issue–they look great rolled up a bit and showing ankle (with flats or converse sneaks) but I was scratching my head about warmer foot wear. Maybe I’ll try these with my Franco Sarto ankle boots and a nifty pair of socks! They are a bit too slim to wear with tall boots, but maybe my brown Timberland hikers will work as well. (Decisions, decisions…)

Leave a Reply