How to Wear a Dress with Pants

Dresses with Pants — Really?

Maybe you’ve seen photos of models or celebrities wearing dresses over jeans and you thought, “Oh! I’m so going to do that.” Or, maybe not.  Perhaps, instead, you’ve thought to yourself that it’s a silly concept that doesn’t have a role in a real woman’s wardrobe.  I get it.  Many of the runway versions really wouldn’t have a place in your closet, especially if you’re finding your dressing preferences are uber casual these days.

Still, the pants-with-your-dress trend carries a few practical qualities with it. If you’ve ever worn a long sweater with leggings and boots, it’s just a small stretch to reach dress-with-pants territory.  Here are a few scenarios where you might like to experiment with the look in your own wardrobe:

  • Dress as shirt. If you miss wearing your dresses that have been out of rotation the last year or so, use them as shirt replacements.  Sure, the dress/pant trend
    how to wear a dress with pants: long shirtdress

    Anthropologie Dress

    can be styled for cutting-edge impact, but there are simple ways to integrate the fashion into your everyday lifestyle. A shirtdress is the easiest way to do this.  Unbutton the bottom to show a jean or legging worn beneath.  If you have a naturally-defined waistline, belt the dress for emphasis.  If your shape is more rectangular, wear it loose and straight.

  • Dress as sun protection. Long day at the beach?  The coverage of a dress protects your sun-drenched skin from further exposure.  It might be a coverup dress that originated as part of a swimsuit ensemble as purchased, or it might be one that you adapt from your
    How to wear a dress with pants: Petit Pois

    Petit Pois by Viviana G

    closet.  For this purpose, think fabrics that are light, breezy, and loose in style (and machine washable if you’re at the beach or pool!).

  • Dress as jacket. Cooler weather, but you don’t want to don a jacket?  The long-sleeve dress worn  over your jeans or slim pants keeps you warm. Whether it’s a sweater version, or a button-up that you
    how to wear a dress with pants: sweater dress

    Peruvian Connection

    wear open, duster-style, you’ll get the benefit of an added layer in a very on-trend style. Like the shirt scenario, wear this belted, or not, depending on your own body’s silhouette.

  • No-effort version. If figuring out “which-dress-with-which-pants?” feels intimidating, take the
    how to wear a dress with pants: jumpsuit

    New York & Company jumpsuit

    How to wear a dress with pants: jumpsuit

    Nordstrom jumpsuit by Kay Unger

    shortcut route: Lots of jumpsuits and rompers are designed with the look of a dress or skirt layered over a pant.  With these, you get a pre-made ensemble with no style-muscle required.  Choose the silhouette in relation to your silhouette.  The variation with fullness below the waist is great for figures that are full in that same zone. A straighter version is well suited to a body that is more rectangular in shape.

    By the way, to keep your look current, go low-key with the accessories.  It’ll allow your dress to stand as the focal point.

Want to learn the best way to wear this trend with your own body’s shape? Check out my on-demand style course, the Figure Friendly Style Formula.

Or for my one-on-one coaching, work with me.

What are your thoughts about wearing dresses over pants?  Have an idea or question? Leave me a comment.  I read and respond to them all.


Patty Buccellato is an image coach and founder of Refined Images. She brings extensive knowledge and expertise to her work with men and women individually, as well as with corporate employee groups.

Patty established Refined Images in 1994, and while her studio is based in Rochester Hills, Michigan, you’ll find her serving clients throughout North America in their homes, offices (normally), and… well, currently on Zoom! To get your FREE copy of Patty’s eBook “The Wardrobe Simplifier” visit Refined Images or contact Patty.

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