Outfit Remix: One Midi Skirt, Four Ways

HTW-midi skirt

As of late, I have really been into mid-length skirts along with the rest of the fashion world, but I realize that this style can be a challenge to wear. I mean, let’s be honest, we come in all different shapes and sizes, and when it comes to awkward length skirts, the outcome has the potential to look, well awkward if not styled correctly.

Take me for example, I have curvy calves from years and years of dance and ballet. This is not a bad thing, but because my ankles are not super petite either, when I wear a skirt that hits at the wrong part of my leg, in my mind, I run the risk of looking short and frumpy. 

However, be that as it may, my love for midi skirts is too deep to let something like length be a deciding factor in whether I wear them or not, so I decided to show you four different ways you can rock the 3/4 length skirt. I created various outfits around my black Eileen Fisher version, but the focus is on the shoe styles. Keep reading to learn more! 

(Disclaimer: This post is not meant to imply that one shouldn’t or can’t where this type of skirt unless they hide their ankles. It is merely a way for me to show how I feel comfortable wearing this style and I only hope to provide further ideas and inspiration when getting dressed.)


(Listed in clockwise order)

1. The Trendy Peep Toe: (Forever 21) The open toe draws the focus to the front area of the shoe, while the folded cuff around the ankle is forgiving with the slight dip in the front. This type of a faux-bootie is a good alternative to a traditional ankle strap peep toe heel. 

2. The Classic Pump:(9-2-5 Kenneth Cole) This is really a no-brainer because in my opinion, everybody’s legs and ankles look longer and leaner in a good old fashioned pump. There is no constriction around the ankle or disruption of lines from the hem of the skirt to the point of the toe. Easy peasy.

3. The Hip Riding Boot:(Aldo) This look is my favorite. A tall boot takes care of all if the issues discussed above. Plus, I think the boots/skirt combo is sort of a throwback to Molly Ringwald’s style in The Breakfast Club. (Love that movie and her style.)

4. The Practical Ankle Boot: (Seychelles) This option is super simple to pull off ( I like to pair socks with it) because if the boot itself is high up enough on your ankle then the skirt only grazes the top of it, letting only a bit of leg and sock show, which eliminates any ankle issues.

If you’d like to see each style again close up, click below!

Outfit Captions:
1. Accessorize Scarf / Vintage Blazer / F21 Shirt / Vintage Belt / Eileen Fisher Skirt / Charlotte Russe Bracelets / F21 Shoes
2. Pearls (gift?) / Loft Sweater / J.Crew Belt / Eileen Fisher Skirt / 9-2-5 Kenneth Cole Shoes
3. Zara Vest / American Apparel V-Neck / Charlotte Russe Bracelets and Necklace / Eileen Fisher Skirt / Aldo Boots
4. Zara Scarf / F21 Ring / Vintage Leather Jacket / Equipment Sleeveless Top / Vintage Belt / Eileen Fisher Skirt /Seychelles Boots
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