How to wear a dress over jeans

Wearing a dress over jeans is one of those next-level styling tricks that you see on street-style blogs during fashion week—it looks amazing but seems way too complicated to actually pull off. I, however, was up for a challenge, and after some experimentation, think I landed an outfit that works. It's all about proportion and strategic unbuttoning so you don't look like a big old blob. Here's how I styled a maxi shirtdress over white skinny jeans.

When it comes to wearing a dress over jeans, I found that a straight-cut shirtdress is the easiest to work with, because you can unbutton it strategically to show a little leg—that way, it's almost like you're wearing a really long top. This one is several years old, but COS pretty much reiterates it every season, so I've linked some very similar styles from them below. This one came with a belt, which I usually wear when I wear this just as a dress, but it was causing all sorts of lumpiness with the jeans underneath, so I found it had cleaner lines unbelted. (You can see the loops in the side view below.) I also rolled up the sleeves to give it a little shape. COS tends to run a little big; this is a size 6 and generous through the hips, but again, that works in my favor here. Oh, and did I mention it has pockets?

Wearing blue jeans with a blue dress would have been an almost Canadian-tuxedo situation, so I decided to create a little contrast with skinny white ankle-length jeans. Yes, these are my old white jeans (last seen with a kimono); I've finally given up on my too-big Madewell jeans. As you may notice in some of these photos, the ones I'm wearing are very low rise; I wish I could find a pair that fits me exactly like these, except like an extra inch or two higher at the waist. Isn't it funny how a few years' time can totally alter your perception of what fits well? Anyway, skinny jeans are definitely the way to go when layering under a dress, as you don't want anything too bulky.

In an ideal world, I would have had a slightly darker-colored shirtdress—I was worried that this outfit didn't have quite enough contrast—so to make up the difference, I layered on one of my favorite jackets, last seen back in October. J.Crew has made a variation of this field jacket for years—mine is probably close to 10 years old, and while it has faded, it has held up incredibly well. The shape and fit are just so good (I'm in a small, for reference).

Accessory-wise, this was my first time this year breaking out my beloved Cult Gaia bag (last seen in August) and my favorite mules of last year (here they are in Pebble Beach). I could have worn a blue bag but didn't want to go too matchy-matchy—one blue accessory was enough.

Coincidentally, I also wore these shoes when we shot in the same location last year. This is literally around the corner from my apartment (and right by the actual Full House house) and, what can I say, I'm a sucker for a living wall. It makes a good backdrop!

OUTFIT DETAILS: J.crew jacket (current season here) | COS dress (current season here and here) | Michael Kors jeans (similar here) | Cult Gaia Ark bag | Sam Edelman Laney mules


Jeans and a Teacup said...

Great job with the styling! It's nice to still be able to wear shirtdresses in cooler weather if you add the pants!

Laura B said...

It's so true about lower rise jeans! I got rid of most of mine a few years back. I love how that shirtdress looks with your white denim!

Jessica Jannenga said...

I love this look on you! I have tried it a couple of time, not sure if I like it on me, but the shirtdress with the white jeans looks great, like a duster. Those vibrant shoes are sweet! They really pop against the lighter colored outfit .
thanks for linking!
jess xx

Shelbee on the Edge said...

Cheryl, I absolutely love the trend of a dress over jeans and I remember wearing it 20 years ago and people looking at me like I had two heads! Lol. But I still wear this trend today! This is a reason I love shirt dresses so much, too. They are so versatile and the perfect style for layering over pants. I also like tee shirt dresses layered over jeans (I have an outfit with that photographed that I haven’t yet shared on my blog). That all being said, I adore this look on you! The chambray shirt dress with white jeans is so great for Spring. And those shoes are magnificent and add just the right pop of color. Love, love, love this look. Well done, my friend!


Ruth said...

I love how you made this appropriate with jeans. The button up is fabulous!

Mica said...

Such a fun way to wear a dress over jeans! this shirt dress works perfectly and I love the blue shoes too! :)

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Hope that you are having a wonderful weekend :)

Away From The Blue