About eight years ago I went through a stage of often wearing A-line dresses or fitted shirtdresses over skinnies and clamdiggers. After a long break from the combination I started wearing it again last year, both for casual and dressy occasions, and am back to enjoying it enormously. I’ve updated the vibe by pairing my frocks with cropped straight or flared jeans, or cropped trousers to showcase the ankle.
Visually, I ADORE the pairing of these silhouettes. A little avant-garde, modern retro, dramatic, elegant, and thoroughly modern. Practically, I find the pairing extremely comfortable because I can get more use out my dresses by extending them into cooler weather. Also, I prefer wearing structured jeans and trousers to leggings or hosiery.
The combination works best with dresses that are fluid or oversized on the waist, and slightly roomy in the hip area to prevent bunching, clinging and gaping. High-waisted bottoms work well because they girdle the midsection and allow the dress to lay flat. Empire cut dresses generally work well because they’re roomy from cut line to hem.
Here are five easy ways to pair dresses with trousers and jeans with an accompanying visual. Use the photos as inspiration to create combinations from your closet, or to shop from the retailers where you prefer to spend your fashion dollars.
1. Dressy Shirtdress & Cropped Straights
Combine a silky shirtdress or shift dress with dressy black cropped straight or flared trousers. Adding a self-tie or belt on the natural waist of a roomy shirtdress works well over high-waisted bottoms because the waistlines are in the same place. Add dressy footwear that works with the length of the trousers. There is no need to wear high heels.
2. Dressy Sack Dress & Cropped Straights
The sack dress here is very long and voluminous, but that’s not essential. Feel free to sport a much shorter dress that’s not quite as roomy. High heels temper the volume, as does wearing cropped pants with narrower hems.
3. Casual Draped Jersey Dress & Skinnies
Casual draped dresses need to be roomy to wear over jeans or trousers so that they don’t cling. Here, the high-low hemline adds visual interest, and the scrunched skinnies are a nice blast from the past. I love that comfortable flat slip-on sneakers were the choice of footwear. Pop a denim jacket over the top for warmth, and Bob’s your uncle.
4. Casual Shirtdress & Cropped Jeans
Combine a casual linen or cotton shirtdress with cropped skinny, straight or flared jeans. Finish off the look with sneakers, casual flats, or sandals. Or combine a blue denim shirtdress with white or black jeans. Scrunch the sleeves and pop the collar if you like. Unbutton a few of the buttons at the bottom of the dress so that you can stride at a fast pace.
5. Tunic & Cropped Staggered Bottoms
Long side slits make this a tunic and not a dress. Pop a long tunic over cropped jeans with staggered hems and add block heel sandals. Dressy cropped trousers are just as fab. Create a column of colour under the tunic with a tank top or camisole if it’s see-through.
I haven’t included a visual, but full-length bell-bottoms or bootcuts with a bit of a heel can work well with a dress or long tunic. It’s a very elegant look, so give that a go if you’re game.
You don’t need to be tall to wear this combination. Petites simply need to adjust proportions so that the lengths of the dresses and tunics aren’t too long.
I wear #1 and #4 frequently. Here are the exact dresses and cropped jeans and trousers from my wardrobe that I pair together to create my versions of the vibe. I finish things off with a dressy low heel, loafer, or flat pair of sandals.
