I just can't do it either, think I look stumpy and goofy. I like the look on other people, but cannot pull it off successfully myself. Agree with the others that your jeans looked rolled a little too high. Anyway, I figure this is a short-term trend and I'm better off sticking with the classic "long" look.

Well the rolling does shorten the leg line when there is skin exposed a la #2 in your original set (not sure to the point where it's super stumpifying, though). The roll you did with the pants pulled down low in your comment later, the second photo there, looks almost as long and lean as the original unrolled line and I love how both the jeans and that roll look on you.

I think with the higher booties like that, you just need a bit less skin showing between the cuff and the shoe. In your sample photos, #3 the roll is on the ankle (quite low), #4 has a LOT of skin showing even with the higher vamped shoe which actually lightens the look a bit, and #5 is back to being really low on the top of the shoe.

I so understand where you're coming from. I like the look on others, but when I try it, I always end up unrolled. The only time I rolled them and liked it was with a pair of Okalas...the jeans were dark wash and I rolled them to the ankle strap. They were a bit stumpifiing but I could live with it. I actually think the photo of the jeans pulled low with no skin showing looks good. You get to participate in the trend, but keep your long leg line.

I definitely prefer your second set of photos with the lower roll and no skin showing (I also like the unrolled one here). What I do when my pants aren't really long enough to turn up twice and hit this low on my leg, is either make a teeny narrow roll, or turn them up once. It's probably my neighborhood hipster influence that I prefer the look of a turnup or roll than unrolled, but still want the whole look to be sleek so avoid showing skin unless the shoe is low vamped, and then tend to show a lot more skin.

I like them rolled on you! However, the difference is definitely in how they fit you vs how they fit the people in the photos. This happens to me all. the. time. Pants that are supposed to fit a certain way look entirely different on me. The legs seem slimmer on you, either due to the size or perhaps your legs are more muscular, or perhaps the pair of jeans you have are cut slightly different (same brand, same size, and many pairs can still fit differently). You could likely get the look in the pictures (if that is what you are after) by going with a different style with a leg that fits looser or straighter on you.

I have embraced "the stump" so they look fine to me. I will say that you are at a distinct perspective disadvantage though, because the stock photos are taken at about knee level and when we take selfies at an angle above that point, the vantage point will be skewed. I prefer to use a mirror which is leaned away from me for checking my outfits, as that compensates somewhat. Unfortunately, I don't have one large enough to take pics with :-(. Maybe I'll try lowering the tripod!

Well, I think they look great on you every which way. I guess my eye has adjusted.

I have short legs and know that rolling does shorten them further, but sometimes I just don't care. If I lived in your climate I would probably be rolling and cuffing all the time, but I might be wearing sandals more than booties in that case. Though I like this with booties, too.

I think another trick to avoid leg-stumpifying is: wear a semi tucked top in a low contrast to the jeans colour.

The fit on the calf of your jeans is tighter, which alters the silhouette. The photos of the other ladies show lots of space around the calf. So if you want THAT visual effect, you need to find jeans that are straighter on the lower leg. (I realize that you can't size up on this style).

I think the rolls on jeans hems add structure, and therefore offset the stumpy factor. Also, higher vamped booties are more elongating than high vamped slip-on sneakers. FWIW, that's what I see.

Thanks, Angie!

I do have big calves. Plus and minus...

I think you look adorable in both styles.

Yes, rolling your jeans is stumpifying (a new word to add to my vocabulary) on most of us, but it's a casual look, so it's okay to look a little less majestic. Angie's advice about wearing a straight jean and higher vamped booties will elongate your look.

But, really, you do look great both ways.

Uh-oh, I feel the urge to step up onto my soapbox: I like to remind the women I work with that we infuse our personalities and our unique body shapes into the clothes we wear. The result is that a particular fashion trend will look completely different from one woman to the next, as it should! To me, that's the fun in fashion -- creating my own unique look out of even the most ubiquitous pair of jeans or cardigan sweater!

Remember to infuse YOU into your outfits. It's not about trends, it's about style.