Wearing dresses over pants or jeans, creating a tunic effect, is an acquired taste. Personally I love the visual effect and combination, and have worn it often over the decades. Pairing fab dresses with cropped skinnies (and later, cropped kick flares) made short dresses wearable and kept me warm. The dresses I combined with pants and jeans were usually shirt, shift or empire cut in silhouette.

This time round, the dresses are longer, and the bottoms a little or a lot more roomy. If you fancy wearing dresses over pants and jeans, these looks might inspire you.

1. Defined Over Fluid

A fit-and-flare shirtdress with an extreme asymmetrical hemline is paired with a pair of blue relaxed straight leg jeans. The jeans are full length. Classic black pumps add height to the outfit, add a dressy component, complement the model’s dark brown hair, and match the black satchel. The self belt of the dress defines the natural waist of the model and adds structure to the outfit.

Defined Over Fluid

2. Soft and Flowing

Here’s a co-ord with dress and pants in the same fabric and pattern. Both are soft, drapey and voluminous. Wear them together and Bob’s your uncle. It’s that easy! Notably, despite the volume and drape, there are subtle design details that give the outfit some structure. The hems of the pants taper back to the ankles. The cuffs of the sleeves taper back to the wrists. The hem of the dress is high-low, which offsets the horizontal line of a straight hem. The breezy look is completed with high-heeled sandals, but feel free to wear flats, low heels, or mules.

Soft and Flowing

3. Lantern and Leggings

If wide and roomier pants and jeans are not your thing, wear skinnies or leggings under dresses. For a more current look, pair longer and somewhat architectural dresses with body-con bottoms. The midi lantern dress here is a great example of the vibe. The black in the dress makes it work well with the leggings. Simple black sandals complete the outfit.

Lantern and Leggings

4. Wide, and Long over Wide

Last, here’s the most fashion-forward version where long wide and unstructured dresses top wide flowing pants. The dresses are midi or midaxi length, and frequently shirtdresses in silhouette. Some of the bottom buttons of the dress are left undone to create the effect of a very long front slit. The “slit” showcases more of the pants, and swooshes as you stride. No need to showcase the midriff if that’s not your thing. Slides and a tote are the casual finishing touches. Note the new shorter full length of the pants, which are as long as you can go wearing open-back and heeled footwear like slides. Longer hems slip under naked heels as your stride which is uncomfortable and precarious.

Wide and Long over Wide

Below are more examples of the vibe. Most of the pants are wide legs, but cropped flares and relaxed straights are shown too. Some of the dresses are VERY long. Some of the shirtdresses are worn open like super long shirts with a layering top like a tank or tee. The third outfit in this collection shows a wrap dress silhouette worn with pants in the same fabric and pattern. The wrap detailing adds an effective bit of structure by defining the waist. Add accessories as desired.

I recently tried a version of the fourth look by combining a roomy midi dress with a pair of wide leg full-length trousers. It happened accidentally in the dressing room when I tried on the dress but hadn’t taken the pants off yet. I looked at the pairing in the mirror, and loved it! It was dramatic, interesting, and elegant to my eye. Comfortable too. The dress is a brighter lime in person, and finishes below my kneecap. I was wearing taupe boots and bag that day, which perfectly matched the outfit. Here are the exact components. I look forward to wearing the outfit properly soon, and might switch to white boots and bag. I’ll need to figure out how to top the outfit with a coat or jacket.