Answer: I received a question in my comments section and I thought it would be more interesting to answer it as a post because other women might be interested in the answer.

I also have an athletic build and I’m only 5′5. So I’m in the middle of petite and not tall enough. You want to look for jeans with a little stretch or that fit in the thigh area. Tailoring might be a requirement. The tailoring cost should only be around $10 – I highly recommend this. With an athletic body or curvy body we crave the illusion od long lines. Boot cut jeans do that, but I also recommend straight jeans and yes you can pull this off. With straight jeans try a pair that is a size bigger than you normally get, have the waist taken in. Straight jeans will give you the slim look and you can pull the boyfriend look! So look for those cuts. Wherever you buy, always ask if they will tailor/hem for free.

In my closet I’ve got, True Religion, Joes Jeans, Lucky, Banana Republic, American Eagle and Mossimo from Target. You heard it right. Mossimo. They are wonderfully soft. With my more expensive jeans I wait until Nordstrom’s has their anniversary sale.

Lucky has been my favorite and has had a lot of sales lately. The Lucky jean I have are Lil Maggie. The online description scared me, but when I went to try them on, they fit like a glove and didn’t flare as much as I thought they would. So I bought one pair. After wearing them twice, I wish I’d bought two pairs. I went back to the store and found out they were popular and kept going back until I was able to find a second pair. My American Eagle jeans are a size larger because they have no stretch. I had the waist tailored for each pair. Banana Republic jeans are comfortable because they stretch. I always need them hemmed and Banana Republic will do it for you for no cost. Mossimo are great jeans, but they more difficult to find because Target can’t keep them on the rack. So grab them if you find a pair that fits you.

In many stores jeans come in short, regular and long. Shop around, but Target, H&M, Macy’s, and JCPenney’s always have great deals. The key to jeans is understanding your body type first, shop around and then be willing to tailor or hem when needed. Try to get the store to offer these services with your purchase, but if they don’t offer that it’s a small price to pay for something that you’ll wear a lot.  Good Luck.

My mother would roll in her grave to know it’s all coming back again. To accomplish the 2009 version of rolling up the cuff, simply take a pair of jeans, roll the cuff, but make sure it’s little loose on the bottom. You don’t want to do this with matchstick denim. Have fun with the style, but don’t look like you put on your guy’s jeans. Don’t pinch the jean either. Get a loose but slimming pair of jeans.

Victoria Secret took their Low Boyfriend Jean, it’s wide leg, rolled them at the cuffs and took a beautiful picture of a model in it. But in real life, the cuffs would be too big or require a pinch in them. If you look at both pictures of the link provided, the jean is form fitting at the waist even though it’s low and so it wouldn’t look right. Now look at Joe’s Jeans Cropped Ex-Lover. This is a loose fit jean but more slim in the leg. The cuff is a little more refined making it ladylike. Another great example is J.Crew’s Vintage Slim Jean.

The boyfriend denim can be accomplished with a pair of jeans already in your closet. With the boyfriend, a loose fit is best because it’s more casual – even if you pair it with heels.