4 Ways to Wear Rolled Jeans

how to wear rolled jeans My gorgeous sister Susanna recently came to visit, and we couldn’t resist a bit of dress up. Below is a typical casual Saturday look, and while I love the purple top and coral wedges, it completely hides her figure (and the shoes). I thought I’d share the four ways we re-styled the look using the tops she brought and her rolled jeans as a base.

BEFORE: Cute but hides the figure – and the shoes!

rolled jeans

Susanna knows that jewel and earth tones look great on her but (like me) struggles with how to take the outfit to the next level with accessories. As a mom, I think it’s hard to add the bit of “drama” that turns a basic casual look into something special. So it was fun to play around with bold accessories and see how they changed up the look. And doesn’t she look great in purple lipstick?!

Outfit 1: Statement Necklace and Glam Wedges

wearing rolled jeans Outfit 1: First, we hiked up her rolled jeans to show off fun gold wedges. As a short girl, I’m always worried that rolling my jeans will cut off the leg line and make me look shorter. But I think the key is making it clear you deliberately rolled the jeans. Make it obvious! Stay away from a tiny, my-pants-are-too-long roll like in the before shot.

Outfit 2: Bold Pink and Coral Wedges

Outfit 2: We had to show off her adorable coral wedges! But I love how great it looks paired with a casual T-shirt and pink accessories – not a color combination Susanna would normally wear. Super fun and easy for a casual Saturday.

Outfit 3: Casual tank top and flats

how to style rolled jeans Outfit 3: You can wear rolled jeans with flats and still look pulled together! We switched out the shirt to a more figure hugging tank top that can be worn with or without the jacket. I swear tank tops are the most versatile clothing item I own. They are light weight enough to wear under a jacket or you can layer two tanks of different colors together.

Outfit 4: Dress it up with heels

rolled jeans evening Outfit 4: I love the look of rolled jeans with a great pair of heels – it feels like an easy dose of sexiness when you’re not wearing a dress. You can take a day look to night just by switching to heels, pulling up your hair and adding a sparkly handbag.

What closet basics do you re-style all the time? Are you a fan of the rolled jeans? (I admit I am – and not just because I’m short and ALL of my pants are too long.)

Special thanks to Brenna at Willows Images for the gorgeous photos and Tess for use of her fabulous accessories.


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  1. says

    I love rolled jeans, but I admit, it’s completely because I’m short and all my pants are too long. :) I really need to learn to hem! Totally love all of these outfit ideas–so cute!

  2. says

    Oh Stephanie! Your sister is just gorgeous. She’s so like you. I too dislike the pants-are-too-long roll. LOL Just a sign that someone can’t sew or are too stingy to take them to a dressmaker! LOL I love those coral wedges and I love all the looks. So fabulous! I think I might ask my sister for a dress up afternoon sometime. Sounds like so much fun.

    Anne xx

  3. says

    oh how fun to play dress up with your sister
    i am soooo jealous
    i just play dress up with my mirror, it rarely gives me feedback!!
    cute looks

  4. says

    This is such a cute look! I am only 4’11 so I could definitely never pull it off, but if I was taller this is how I would always wear my jeans. xo

  5. says

    Love this post..each photo w accessories is cuter than the next and see how EASY it is to take basic to fabulous with a few simple additions. I tell my mommy on the go clients this ALL the time…just throw on a cool necklace and great shoe OR layer a few tops with different colors textures and you can still be comfortable and casual but SUPER CHIC!
    Loving that cool clutch in the last photo.

  6. joen says

    I love the gold wedges with the rolled jeans. I have been trying to accessorize more myself. I have a friend that always looks put together from head to toe and I think why didn’t I think of that! because its always items I already have too but never think to put on.

  7. says

    I roll my jeans as well! I love the look of it. It makes jeans able to wear longer in the spring. Thanks for letting me know I am not the only one who likes my rolled jeans. :)

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