Ever since Carrie Bradshaw sauntered down a New York street in a dress over pants, I’ve been smitten. Truth? I never stopped. And this season, fashion finally caught up, so I can retire my defense speech and hand you a playbook.

I love reaching for pants when I get dressed. I also love playing with length, shape, texture, and density. A dress-over-pants look ticks every box, and when it’s done right, it reads relaxed confidence. But this isn’t about tossing a random frock over denim and calling it edgy. There’s an art to the stack.

Hem choreography. Let the pant leg read. Choose a mini or shorter midi dress. If you go with a longer shirt dress undo most of the buttons. One lonely centimeter of pant peeking out is not the vibe.
We want to pair structure with flow. A tailored bootcut pant or jean under a fluid slip dress, or a cropped cigarette slack under a swingy mini are both winners and the most flattering foundations for this look. Shout out to capris - they are having a moment and are the perfect foil for a frock. The more adventurous might want to try joggers or balloon pants.
Edit the layers. Too many layers = visual noise. Keep the last layer small - a shrug, cropped cardi, fitted crew neck sweater or neat satin bolero like Carrie.

You don’t want to look like you threw a nightgown over jeans. Pick dresses with intentional fabric (crepe, knit, weighty satin) and real finishing (hems, slits, seaming).
Avoid baggy over baggy. Disheveled and oversized is a choice; leave that one for Adam Sandler.
If you’re shy to try, go monotone. This way the silhouette does the talking. (Just don’t let the dress run too long; you want pant presence, not a whisper.)

Opt for a pointed toe (slingbacks, sleek ankle boots) to lengthen the line.
Play with textures. Wools with satins, crepes with knits, denim with silk.

Short over long reminds me of the daily work of holding strength with dignity; foundation first, grace on top. “She is clothed with strength and dignity” (Prov. 31:25) isn’t a slogan; it’s a critical seam to stitch. I’ve noticed many heroines of scripture rocking this combo. Sarah shows us strength to wait and dignity to hope when the timeline stretches thin. Esther models strength to risk -“If I perish, I perish”, and dignity to petition with poise after prayer and fasting. Rahab stakes everything on a scarlet cord and pairs strength to stand with God’s people, dignity to welcome a different future. Mary steps into a room that wasn’t her fan base and anoints Jesus anyway, modeling strength to enter, dignity in tenderness.

That’s the balance I’m after: the foundation, clear boundaries, quiet backbone, the disciplines that hold you (prayer, wise counsel, truth-telling) under a dignity that moves - ease, expression, a willingness to be obedient and to surrender. In scripture, we are advised to put on the armor of God but also to clothe ourselves in compassion, kindness, and humility . Too much structure without movement hardens into rule-keeping; too much movement without structure drifts into noise. But when strength carries dignity, when the base is set and the top can breathe, the look reads true, and so does the life.

Some days the proportions land perfectly; other days the hem needs editing. That’s discipleship. Adjust the length, swap the pants, try again. Get the base right, let the visible grace do its work, and walk out knowing the proportions, of your outfit and your heart, are headed in the right direction.