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How to Wear a Midi Skirt to Work

By Bridgetteraes @BridgetteRaes

How to wear a midi skirt The midi skirt has been making a comeback for several years now.  In fact, back in 2011 I wrote a post on its return and included my tips on how to wear a midi skirt, even though I didn’t like the trend all that much.  I’m still not a huge fan because it is such an awkward skirt length to wear and, quite frankly, involves a lot of thought and time to get right.  However, if the midi skirt is right for you it can be a nice change to have in the closet, especially with spring coming.

For work, the midi skirt can be a nice change.  It’s long enough to be more modest and office appropriate and, depending on the silhouette and fabric, can work well in a conservative or more casual office environment.  Plus, with just a few tweaks a work midi can easily be worn on the weekends.

So given its versatility why do I have such an issue with the midi skirt?  Well, the style can be really awkward to wear and if not worn properly can make a person look short, squat, bottom heavy and dumpy– none of which are adjectives most women want to be associated with.  Yet, with the right approach it can be easy to correct these dressing issues, some of which I will share here.

The best length of a midi skirt

A skirt can be considered a midi as long as the length falls somewhere between below the knee to the ankle.  This is why the midi skirt can be such an enormous fail.  The worst length of a midi skirt is when the length ends right at the widest part of the calves.  Unless you want to look like you instantly gained 15 lbs. in your legs overnight, make sure the hem of your midi skirt is below or above this point.

Too much fullness doesn’t hide anything

The knee-jerk reaction of most women when they are bottom heavy layer that area with big, flowy bottoms, like full skirts.  While this strategy can work, swishy midi skirts can sometimes make a bottom heavy look like the shape she is trying to avoid- a big ‘A’ shape.  If you have large thighs, and are counting on your midi skirt to hide them, make sure there isn’t a lot of fullness, like pleats or gathers, in the waist of your midi skirt, that the skirt has a clean shape and that the hem does not end at that awkward “fat calf” length.

What to wear with midi skirts

Regardless of whether your midi skirt is full or slim like a pencil, extra care needs to be paid to what you wear with these skirts.  Shape and proportion are important.  With a full midi a top with waist shape or one that is belted will show off the waist and create a more proportional look.  A full top with a full skirt just creates a sloppy, pup-tent look.  For a slim midi skirt, shape is equally important as is length.  Tops or jackets that are too long look awkward with a midi skirt.  Stick to slimmer, shorter pieces.

How to wear a midi skirt to work

Here are three work outfits that I styled together for work.  Check them out, along with my additional tips to show you how to embrace the midi skirt with style.

Outfit #1

What am I going to wear to work tomorrow? Look 3

I love this midi skirt skirt from Reiss.  If I had to wear a midi I would choose this one because it is slim (much more flattering on a person who is bottom heavy with large calves and ankles, like me) and has a gorgeous back slit up the back that isn’t too high.  However, despite my appreciation for the skirt, the length is still a bit awkward.  Given that, I decided to style this skirt with nude shoes to balance out the fact that the hem of the skirt ends at a slightly in-between place.  Nude shoes not only create leg length but leg slimness whereas a darker shoe or, worse, an ankle strap can makes leg look shorter and thicker.

For a more professional work environment, I styled this skirt with a Vince Camuto top, a Mango cardigan and, for a pop of red, a large wrap scarf and red earrings by Janna Conner.  The outfit is finished with a Furla handbag and Stella & Dot necklace.

Outfit #2

What am I going to wear to work tomorrow? Look 2

For a more casual work environment you may be thinking that a skirt like this can be great, and you’d be right.  It can be perfect for spring– it’s longer, easy, breezy, cool for warm weather, etc.  However, before you run out and stock up on skirts like this one from Boden, I must warn you, these skirts that are in lightweight jersey are often very flimsy and don’t really contain the body, especially if you are bottom heavy.  To avoid what I call the “fat in the Ziploc bag” syndrome, consider putting some structure, like shapewear or at least panties that give you some hold, under this skirt.   Yes, I live in flimsy, jersey skirts and dresses in the spring and summer, but I never leave the house without the right undergarments underneath.  God didn’t give me enough tone in my backside to consider otherwise.

Additionally, in this outfit, you will see I belted this denim top from J. Crew with a belt from Lauren Ralph Lauren.  I did this to not only create a business-causal look, but to bring balance into the outfit.  The waist is important when wearing fluid midi-skirts to avoid looking like one big shapeless mess.  Lastly, I chose  these coral shoes from Anthropologie with a slight heel to further balance the outfit.   A heel can add proportional height for those who are either petite or who have shorter legs and an ankle strap is fine for those who have slimmer ankles and calves.  The outfit is finished with a Coach handbag and gold earrings from Ali NY.

Outfit #3

What am I going to wear to work tomorrow? Look 1

A pleated midi skirt needs some direction in order to wear properly.  While this is a sweet professional look, it’s not for everyone, I am sorry to say.  Pleated maxis can be great if you don’t carry a lot of weight in the tummy area because pleats can add bulk over the tummy.  One way to wear pleated skirts with tummies is to look for pleats that are stitched down a few inches over the abdomen area.  This will guarantee flatness.  Additionally, unless the pleats in the fabric has been treated to keep after laundering, pleats can be very challenging to maintain.  I am not saying to never purchase a pleated skirt, just make sure it is right for you and that you will be able to easily maintain the fabric.

Be that as it may, this skirt from J. Crew is lovely for someone with a slight frame, more of a boyish figure or who is narrow in the hips.  Plus it is in a color that can be easily made professional looking with darker neutrals, like these polka dot slingback flats from Boden.  Again, to avoid looking shapeless, this cardigan from Modcloth was added.  What is created is a darling, retro shape that is perfect for a casual office environment.  Lastly, to bring in a third color (which you all know about how to do now), the yellow bag from Boden offsets the matchy look and the navy bracelet further grounds the lightness of the skirt with richness and the earrings  by Privileged Gold add some polish near the face in a feminine manner.

One last tip about flats with full midi skirts.  If you are going to wear them make sure that the hem of your skirt does NOT end at the widest part of your calves.  I don’t care if you are an emaciated twig, flats and skirt hems that are hemmed to emphasize the widest part of the calves will make even the thinnest look like the hippos in Fantasia.  Cute for cartoon animals but tragic looking on most women.

how to wear a midi skirt

How to Wear a Midi Skirt to Work
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