How to Style a Black Midi Dress: 4 Easy Outfit Formulas
Four EASY WAYS TO STYLe
Your favorite black dress
If you’ve ever stood in front of your closet thinking “I have nothing to wear”… start here!
A few weeks ago, I shared 4 Ways to Style Skorts, and the response was so good that I had to bring the concept back. This time, we’re styling a true wardrobe classic: the black dress. Like a skort, it’s endlessly versatile, but a little chicer, a little more timeless, and (bonus!) the exact one I’m wearing is under $50. Whether you’re headed to the office, running errands, or dressing up for a night out, here are four ways I’ve recently styled mine to help you get the most out of this closet MVP.
Laid-Back, But Put-Together
A classic denim jacket and simple white slides give this dress an easy, laid-back vibe, perfect for weekend errands, a casual coffee date, or brunch with friends. When the temps drop, just swap the sandals for a ballet flat or low-profile sneaker to keep the look just as effortless and seasonally on point.
DRESS (XXL)
SIMILAR DRESS (USE CARALYN15)
DENIM JACKET (1X)
Date Night with an edge
Layer on a black leather jacket and add a sleek heeled sandal, and suddenly this dress is ready for anything after dark. Perfect for date night, a concert, or dinner with friends, this combo gives just the right amount of edge without trying too hard.
DRESS (XXL)
SIMILAR DRESS (USE CARALYN15)
MOTO JACKET (XL)
The Functional Favorite
This look is equal parts practical and polished. A striped button-down, crossbody belt bag, and sporty sneakers make it ideal for travel days, park hangs, or chasing a busy toddler, while still feeling put-together. Bonus: everything moves with you, not against you.
DRESS (XXL)
SIMILAR DRESS (USE CARALYN15)
BUTTON DOWN (XL)
SIMILAR BUTTON DOWN (USE CARALYN15) | SIMILAR BUTTON DOWN
Effortlessly Office-Ready
A structured blazer instantly elevates this black dress for work, meetings, or a coffee date where you want to look like you have your life together. Paired with a slingback or a clean flat, it’s an effortlessly chic option for anything business-ish without being boring.
DRESS (XXL)
SIMILAR DRESS (USE CARALYN15)
SIMILAR BLAZER | SIMILAR BLAZER | SIMILAR BLAZER
For more work-friendly outfit inspiration, see this recent post!
Thanks for reading!
The beauty of a black (or navy) dress is in its versatility. It’s truly a blank canvas you can style a hundred different ways. With just a few simple swaps, you can take it from casual to dressy, desk to dinner, errands to evening out… You get the idea.
If you’re feeling inspired, don’t stop here! Check out my blog for more outfit ideas, styling tips, and seasonal wardrobe staples I actually wear on repeat. And if you’re ready to recreate these looks, everything’s linked over on my LTK page for easy browsing.
Which look would you try first? Do you love posts like this? Drop your fave in the comments, I love hearing what speaks to you!
xx CMK
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Photos by Ryan Kell