The pencil skirt is easy to pair with tops because wearing body con, tailored and oversized fits with a sleek bottom makes for a flattering combination. But throw in a full skirt and suddenly you’re scrambling for the right top because feelings of “dumpy and frumpy” set in at the drop of a hat. Tops are either too long, too wide, too styled, or you just don’t want to wear a tucked top that is fitted around the midriff. You end up throwing on the pencil skirt instead. 

I can’t tell you how many flared orphaned skirts I find when I review closets for clients. It’s an epidemic. But no more! Full skirts will be trending for many seasons to come, so let’s find some tops for them.

You might need to evolve your thinking about outfit proportions. Wearing a short, fitted untucked top with a flared skirt is a no-brainer because it defines the waist, flatters the body, and makes you feel fab. But fashion has evolved to the extent that wearing a somewhat roomier fit on top is just as stylish, and definitely more fashion forward. Wearing volume on top of volume can work if there is also the right amount of structure. 

Here are 13 top options for the flared skirt. Note that these types of tops can work for most styles of flared skirt. But for simplicity’s sake I’ve chosen a generic style so that you can visualize each of the tops with the skirt more easily. Some of the tops define the waist, some are relaxed and less waist-defining, and some are oversized and waist surrendering. Some tops are best worn tucked while others should be left untucked.

  1. Shell Top: These silky and slippery tops are best worn tucked. 
  2. Button Through Shirt or Blouse: Tailored shirts and blouses should be tucked. 
  3. Cropped High-Low Pullover: The cropped nature and high-low hemline showcases the waistline of the skirt, thereby providing structure to the outfit. The top does not need to be midriff baring, and a roomy fit works extra well in a cropped length. 
  4. Cropped Banded Pullover: The banded bottom provides waistline structure while the rest of the top is relaxed. 
  5. Relaxed Pullover or Knitted Top: This top is longer and should be worn with the band on the hips so that the top creates a scrunched and “blouson” effect – much like a flapper dress. The waist is undefined, but the tailored band pulls structure back into the outfit. Semi-tucking this option is another way to go.
  6. Fitted Cropped Cardigan: Button up the cardigan and wear it like a top over the skirt. 
  7. Sassy Sweatshirt: This oversized pairing is fashion forward. The band gives the outfit structure. The high-low hemline is optional, but a great idea if you’re after even more structure. I find that scrunching the sleeves adds even more structure. As odd as it sounds, showing forearm skin can add structure to an outfit. 
  8. Fitted Cropped Lace Shell Top: This is an example of the type of short, fitted untucked top that always works well. Choose your neckline and sleeve style.
  9. Fitted Tank Top: This is a longer version of number 8 that can also be worn untucked and possibly belted. Choose your neckline and sleeve style.
  10. V-Neck Banded Top: This top has a similar fit to the cropped banded pullover, with the band defining the waist while the rest of the fit is relaxed. The wide band is a feature while the V-neck is elongating. 
  11. Drape Top: Loosely tailored wrap tops that drape can look amazing over a flared skirt when they aren’t too long when untucked. They provide ample structure if there is a hint of a waist and the hem fits snugly against the body. 
  12. Fitted Turtleneck: These work both tucked and untucked. Don’t wear them too long when untucked. Ruching the side seams shortens the length and flatters proportions. If the turtleneck is banded and relaxed in fit, the top becomes a turtleneck version of number 5. 
  13. Fitted T-Shirt: Wear it tucked or untucked and a little ruched at the side seams. Choose your neckline and sleeve style. 

Not all of these options are conventionally flattering, but that isn’t always what style is about. Furthermore, sometimes we have to see a combination a few times before our eye adjusts to the proportions. The important point is that fashion has moved on and there are now many, many top options for flared skirts. And if you end up adding one or two more options to your list of go-to tops for flared skirts, then so much the better. 

My clients wear options 1, 2, 6, 8, 9, 12 and 13 frequently. Some are all over options 3, 4, 5 and 11. I have a few dabbling with 7 and 10. I’ve been wearing 2, 6 and 12 forever, but have been favouring 3 and 5 more recently because the combinations feel fresh. I also want to try option 7 as soon as I find the right sassy sweatshirt.  

If you have further questions on how to match tops with flared skirts, feel free to ask them in the comments section. Here’s to no more orphaned skirts!