Today's Everyday Fashion: Tricky Trousers

I have a real love-hate relationship with these pants. On the one hand, I love a cropped trouser and I think they are such a chic alternative to your usual (boring) work pant! On the other hand, they have a drop-crotch/somewhat harem style that just doesn't look good when you wear something short. So it's tough to find things that look "right" with them. Thankfully, I only paid $15 for them. (I also took them to a tailor - they look better now, but still didn't quite come out how I wanted them to!) I recently came up with today's look based on this Gap photo, and it got me thinking of other outfits I've done with these pants.... so I picked three and shared them below! I think overall the only one that really works is #2, because the shirt is long enough to cover the top part of the pants. Not ideal to have a pair of pants that only work with super-long shirts, but I love how they look in #2 so I will attempt to do more outfits like that one in the future! Do you agree that #2 is the only outfit "win"? How would you style these tricky trousers?

Inspiration photo: Gap
Leather jacket: Banana Republic, $150
Sweater: Banana Republic,  old
Pants: Gap, $15
Shoes: Restricted from Endless, $40
Necklace: Stella & Dot
Ring: My Stella & Dot website, $49

Total win. (My outfit was in InStyle magazine!) This shirt is really long, but somewhat sheer, so it provides the right amount of coverage without looking frumpy. One of my favorite looks of all time! (Original post here.)

Okay. This shirt is just barely long enough and the shoes elongate my feet, making the pants more flattering. I want to zest up this outfit a little though - maybe add a scarf or sweater vest? And ideally I wish the shirt was just a tad longer. (Original post here.)

Total fail. I think this blazer and shirt are just too short for these pants, unfortunately. I think I need to style these pants more like leggings and stick to very long shirts like look #2 going forward! Overall, untraditional clothing items like these pants can be tough to style, but I think it's worth the trial and error to create outfit "wins" like #2. (Original post here.)

Get your own tricky trousers! (j/k, hopefully these will fit like a dream!)

1. Forever 21 cropped trouser, $22.80
2. Frech Connection cropped trouser, $29
3. Calvin Klein cropped trouser, $49