Let me tell you about the last time I wore a pleated skirt. I was in my mid-twenties, I was a fashion designer and we had sampled a pleated maxi to possibly put in the line. One of the perks of my job was I often got the samples we made for free. This was a real perk for a young girl, new to NYC, and broke. While I may have been young, I was still curvy, a smaller curvy person I am now, but still curvy. I wore the skirt out thinking I would look cool and current and instead, when I looked in the mirror, I looked bottom-heavy and dumpy. I never wore pleated skirts again.

Pleated skirts can be tricky to wear which is why I probably got a comment from a reader asking for me to do a post on them. In theory, pleated skirts shouldn’t be hard but I have found that the people who look best in them are the people who have nothing to hide, like long, lanky women with 5% body fat. It got me thinking of some workarounds for those who want to wear pleated skirts in a figure-flattering way. Check out the looks and tips below and shop for more pleated skirts at the end of this post.


Outfit #1

pleated skirts

Let’s start with the potential issues with a skirt like one from Ted Baker. If you have rounder hips, the pleats at the hip area are going to emphasize the roundness of them, especially with the defined black lines on each pleat. This was one of the problems that happened to me when I wore my pleated skirt. This is definitely more suitable for someone with straighter hips or fewer curves. The second problem is the length. This skirt is a midi and tends to fall right at the widest point of the calves and will make them look larger. Anyone with large calves and ankles knows this is a huge no-no. So if you’re narrow with slim ankles and calves, have at it!

I styled the Ted Baker skirt with a blush top and cropped ivory cardigan from L’Agence and finished the look with blush flats from M.M. Lafleur and a shades-of-pink necklace from Anthropologie.

Outfit #2

pleated skirts

A way to create a longer, leaner look in a pleated skirt is to create a monochromatic column. This creates less division between your top and bottom half of your body and when the body is cut right across the mid-section it can make you look heavier. This pleated skirt from Theory is also longer so it won’t cut you right across the heaviest section of your calves. I styled the Theory skirt with a compact crepe turtleneck, also from Theory to ensure both navy shades are close, a pair of navy flats from Linea Paolo, and stone drop earrings from Anna Beck. One caveat, pleated skirts are difficult enough to hem but even harder when they have a handkerchief hem like this one does. Given the length, this skirt might be tough to wear if you are petite.

Outfit #3

pleated skirts

Pleats aren’t just for midis and maxis, however, you don’t want to look like a schoolgirl in a super short one either. This pleated skirt from Tory Burch hits right below the knee which is that sweet spot for making legs look their finest. Another benefit of this skirt is the higher and sturdier waistband that can help to create a better waist shape. I styled this skirt with a white button-down shirt, tan block heel pumps from Clarks, and tortoise link earrings from Banana Republic.

Outfit #4

pleated skirts

This pleated skirt from J.Crew falls mid-calf, so be careful despite the fact that J.Crew calls this a flattering length. What this skirt does have going for it is it has knife pleats vs. accordion pleats, which means the pleats go in one direction. These larger pleats will more likely lie flat than accordion pleats will. Knife pleats are also easier to wear with shirts untucked than accordion pleats are because they lay flat and won’t cause bumps when something slim is worn over it.

I styled this skirt with a basic silk t-shirt from Cuyana, a pair of navy strappy sandals and pearlized link necklace from Ann Taylor.

Outfit #5

pleated skirts

This last casual pleated skirt look has stitched down pleats over the hips which can be very beneficial. The flare of the skirt from the pleats starts lower and can make a person look less hippy or bottom-heavy. I styled this skirt from Boden with a tie front chambray shirt from Karen Kane, slip-on espadrilles with cute French Bulldogs from Soludos, and charm hoop earrings from LOFT.

Shop for Pleated Skirts

Now that you know what to look for in pleated skirts, check out these additional styles here.