Gone are the days when wearing heels (and very high heels) with skirts and dresses elevated your style. It’s more trendy and current than ever to wear skirts with flats, which in most cases is more comfortable, practical and casual. Of course, wearing skirts with heeled footwear is a classic, and you should by all means keep on doing just that if it’s your preference.

The definition of a flat is not clear-cut. I think of heels up to an inch high as flats. Heels between an inch and a quarter and two inches are low heels. Anything higher than that is a high or very high heel.

Here are some casual and dressy skirt and flats outfits to get you started. It’s all about satisfying your figure flattering priorities and wearing what makes you feel fab. Choose any colour palette. 

1. Dressy Blazer & Loafers

These proportions have a fab ‘80s integrity. Combine a dressy pencil skirt with a layering top and blazer. Finish off the look with a dressy loafer or flat mule, and a structured bag. Tucking the top lengthens the leg line from the hips upward, and offsets the longer length of the blazer. If you don’t want to tuck the top, wear a shorter top and blazer.

Halogen Lace and Pinstripe Pencil Skirt

2. Casual Khakis & Slides/Sandals

Combine a casual skirt with a striped, printed or solid semi-tucked tee, and finish things off with flat slides, sandals and a crossbody bag. The khaki skirt can be substituted for a denim one and the formula is the same. Add colour or keep things neutral.


3. Moody Shine & Slides

I like the relaxed elegant vibe of this look. The dressy items are dressed down to look more down to earth. Combine a dressy tank, shell or blouse with a dressy pencil or A-line skirt. Semi-tuck it if you need to lengthen the leg line of a midi. Add dressy flat mules or flats, and a structured bag. I’m not as fond of the slides here, but they work. Keeping the palette dark has a moody effect.


4. Fit-and-Flare with Mules

This is a dressy outfit with flats. I love that! Combine a flared midi skirt with a tucked or semi-tucked top. A roomy cropped top will also work. Finish off the look with flat dressy mules, sandals or ballet flats, and a clutch. You’re ready for a Summer wedding. The low-contrast mules with pointy toes do a good job of lengthening the lower leg when the heel is flat.


I wear all my Summer skirts with flats these days. My current favourites are a new blue and turquoise lace skirt, and an old acid wash denim skirt. Both are knee-covering pencil silhouettes. I like to wear them with an assortment of blue and white tops that I semi or fully tuck. A few of the tops can be worn untucked. I finish off the look with white pearls, eyewear, and white or blush loafers or mules. Very occasionally, I’ll wear white sneakers with the denim skirt. The bag can match the shoes, or I’ll throw in another colour like citron or turquoise to break up the palette. Here are the exact items from my wardrobe that create those outfits.