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How To Wear A Midi Skirt

This post is sponsored by Walmart.
Thank you for supporting A Well Styled Life sponsors.

Life is not all jeans and sneakers for most women and some days you want to take it up a notch. That needn’t mean breaking the bank so I’m back today with another budget-friendly outfit that works day to night. This look will take you from a busy day at work to a night on the town with ease.

Jennifer Connolly of A Well Styled Life wearing midi skirt with kitten heels and black turtleneck
classic turtleneck / midi skirt / shoulder bag / kitten heel shoes

Walmart has stepped into the fashion market in a big way this year with exciting new brands for the entire family. Their quality is impressive, and their price points make staying on top of new trends easy on your wallet.Jennifer Connolly of A Well Styled Life wearing midi skirt and kitten heels

I created today’s look around this Printed Midi Skirt. The slip style skirt is a classic that is very popular this fall…especially in animal print. This one is a soft blend of cream, ivory, and taupe brown so the snakeskin print is subtler than most.

Jennifer Connolly of A Well Styled Life showing flattering length of midi skirt
classic turtleneck / midi skirt / shoulder bag / kitten heel shoes

A midi skirt’s length is somewhere between a mini and maxi skirt. There’s no hard and fast rule about how long it should be but know that where it ends on your leg can make or break how it looks. The most flattering length for any skirt is a spot on your leg where it indents or narrows. Typically, that’s just above the knee, right below the knee, the top of your calf, the bottom of your calf and above your ankle. If your skirt stops mid-calf it tends to widen the look of your leg, which few women like. For a midi skirt, the bottom of your calf is the most common, but because I’m petite, I look better with it just above my calf.


This skirt has an elastic waistband which makes it simple to simply fold over until you get the right length. Here is the skirt length without adjustment.Jennifer Connolly of A Well Styled Life wearing a midi skirt and black turtleneck

Here it is with the waistband folded to get a more flattering length.Jennifer Connolly wearing a midi skirt

Here is a side by side comparison. Jennifer Connolly showing best length for a midi skirtIf I was taller and had long legs, I could wear it as designed. You know how strongly I believe in altering a garment to fit you best, so simply folding a waistband is a no brainer for me.Jennifer Connolly of A Well Styled Life wearing kitten heels with midi skirt

These Faux Suede Kitten heels have a feminine little ruffle detail on top. The low vamp helps elongate the portion of your legs which are visible and helps your legs look longer. It has a small platform which renders this heel the equivalent of 1″, making it the micro-kitten heel trend I told you I was looking for here.

Jennifer Connolly wearing midi skirt and turtleneck sweater
classic turtleneck / midi skirt / shoulder bag / kitten heel shoes

Midi skirts look best when you balance them with a top that is close to your body and ends near your waist. To balance the longer, looser skirt, I chose a Jennifer Connolly of A Well Styled Life showing how to wear a midi skirt

This vegan bucket bag from Walamart

Midi skirts are a very ladylike look. The trick to wearing one without looking frumpy is the length and the proportions. Have you tried wearing a midi lately?

Do you alter things to fit your body?

Thanks for reading and be sure to wear what makes you feel confident.


  1. Almost always have to adjust something. Sleeve length is my biggest challenge. It’s hard to alter tailored shirts sleeves. One reason I like shopping thrift stores for tops is bec the shirts have usually shrunk and the sleeve length fits!
    I like skirts just below the knee cap and at the ankle. Mid calf looks terrible on me.. very dowdy. I look 20 pounds heavier.
    Proportion is everything.

  2. My sincere condolences on your unfortunate hair experience! Coincidentally, just the other day I recalled a decision 40+ years ago to add bangs to my then shoulder-length style. I should have left the salon when the stylist mentioned that she had a migraine. Rather than straight bangs across my forehead, she cut an ugly short layer that extended halfway to the crown. It took months to get over that disaster!

    1. Ouch! It’s really hard to leave a salon once you’ve sat in the chair. I’ve been there

  3. Very pretty and I so appreciate the guidance/tips. Would you wear a taupe/sand colored shoe with it to elongate your legs also? TYIA

  4. Jan Maier says:

    I want to see the hair cut you don’t like. Pretty Please!

    1. It’s dark lowlights! I feel like a brunette. I’ll snap one

  5. Totally understand the hair dilemma! We moved to Sacramento from Oregon last spring. I’ve found a pretty good colorist, but her cuts are still not quite right. Yay that hair grows!!!! I wear skirts a lot – summer is a white jean skirt from Talbots which hits right below the knee, and winter is a blue jean skirt from Chico’s which hits right at the knees. In winter I wear leggings, tights, flats, boots or booties with the short jean skirt. Both skirts make me feel confident & polished. Easy peasy!! Thanks for your Walmart tips!!!

  6. I hear you on bad haircuts. I booked a haircut & highlights the beginning of May for August (when we return from our boat trip) with my hairstylist. You can imagine my surprise when a very young lady comes out to get me, I told her there was a mistake and went to the front desk to sort it out. Nope! I was booked in with her and was told, “She is very good”. Well, I have been struggling to get my hair to look good ever since. I wanted to let it grow out a bit before I go see the stylist I prefer. That is a long way to travel for a good cut, Jennifer.

    I never feel good in a midi skirt. I like mine to be just above the knee or long – no in between. It seems Wal-Mart has upped it’s game. I never shop there but will drop in and see for myself.

  7. Carolyn Robinson says:

    Walked into VonMaur department store the other day and they were showing midi-skirts and dresses! Being just over 5′ I spent my high school years rolling over waistbands to get my skirts to a better length. Haven’t worn skirts in years but might check out the new midi’s.

  8. You go, Walmart! I love what they are doing now with fashion! This skirt is something I would try shorter with tights. It looks like a great skirt! Thanks for informing us Jennifer!

  9. I always enjoy reading your blog and sometimes look into the details of an article of clothing on the merchant’s website. I went to the Walmart website for information on the skirt in this book and read some of the reviews. One review was very negative on the quality of the fabric explaining that after one wash there was considerable shrinkage and fraying of the stitching. I would be hesitant to purchase clothing from Walmart unless I personally inspected the item to check the type of fabric, the stitching and washing instructions.

  10. This is a great look, Jennifer. Fit is everything.

  11. Yes I alter a lot, to Diane above, my local tailor was able to shorten my cashmere sweaters, both hem and sleeves. I hem my dresses and skirts to around the knee, so some of the new longer styles, if I buy any, will be shortened. I am always looking for shorter jackets, 19” or less, I guess bolero style, it seems to work on me.

  12. I have been altering my clothing for years and before that, while in my teens and into my 30’s, I made almost everything that I wore. Now, if I shop carefully at shops that offer petite sizing, I often do not have to alter my clothing. Ankle pants are the best invention ever because I don’t have to alter them. Yes, they hit me a little lower than intended, but it is right where my leg and ankle meet and sometimes even higher. Most often the hem on full length pants will have to be shortened, even in a petite size. I need a 27 inch length and most petite full length pants are 28-29 inches in length. Where I have the biggest challenge is buying sweaters since they can’t be shortened. Most are about two inches too long for my short torso and hit me too low making me look even shorter. Knit tops are the same way, but I do have a serger and I can alter knits if the bottom hem is simple. Since I love pullover sweaters for the cold Winter months, I have to do a lot of searching to find sweaters that look right on me. When I find them, I usually buy one in every color. Thanks Jennifer for your very informative posts.

  13. Excellent tips and absolutely love this outfit on you Jennifer. Regarding alterations; as a hobby sewer and because I feel the fit of a garment is very important, a definite yes to your question. Also because I wear a size 4 or 6 (on the average ) and due to my height/long leg length I often find myself either having to adjust a pattern and/or , add a false lower hem to an industrial made garment. -Brenda-
    P.S.: With reference to Walmart; two pairs of my favourite cropped summer weight jeans are from there which I feel are just as comparable to my high-end ones in fabric/fit/workmanship.

    1. Brenda–Your body fit issues sound like mine. Would you explain what you mean by “add a false lower hem”–I sew, but am better at geometric shapes like pillows and table skirts than fitting the human form and alterations. Do you mean you let out whatever hem there is, and then add additional fabric/seam binding, etc. to form a new hem? Do you have problems removing the already-pressed hemline (my mother taught me to iron with vinegar to remove that, in stubborn cases)?

      1. @Mary: Yes, let down what ever hem there is and the type of false hem you use depends basically upon its fabric type. For example; a conventional single/narrow type bias tape works well on a light weight fabric (i.e.: lining) whereas you might wish to use a single fold wide or open double-fold bias tape for a bottom-weight fabric (i.e.: denim). For attaching; rather than a straight stitch I find a very narrow zig zag stitch works well (which is also a haute coutre method used ‘some’ times for seam allowances when working with sheer fabric.) To eliminate the crease line; a) if washable let down the hem first then launder and preferably air dry as you do not want to be setting the crease b) with your iron give it a blast of steam and using its tip; press (not to be confused with iron) from the right side on a hard surface, then repeat on the wrong side of the garment. For fabrics that cannot be laundered; application of vinegar does work however it sometimes can stain or discolour a fabric. i.e.: Silk Hope this will be of help .. ☺. -Brenda-

      2. Thank you, Brenda, for your detailed instructions! Very helpful!

  14. Laura Jane says:

    I do alter things to fit my body. Well, actually I pay others to alter them because I can’t sew! I have a hard time finding tops and blouses that fit properly because I’m short-waisted (but not short in height) and have a large bust for my body size. It’s frustrating to buy new clothing and not be able wear it right away, but everything looks so much better when it fits your body well, as you demonstrated with the two different skirt lengths! Love the idea of simply folding over the top of the skirt instead of hemming.

  15. I really like the skirt! Thank you for this post, for a variety of reasons I often wear dresses and skirts. It is hard to find someone/bloggers who show skirts and dressses, always pants?so I really appreciate your post. I am going to buy the skirt TODAY!

  16. I have lots of empathy re: your new haircut. I have just finished growing out a terrible cut, but am now afraid to let anyone near me with a scissors for fear it will happen again. Good luck!!

  17. Gail Schwartz says:

    Thanks for the length analysis. Very helpful. Please find a hairdresser close to your new home! I had to do that and it worked out very well.

  18. I like the look of a midi skirt, but dressing my petite body can be so problematic. Jennifer, thank you for the great tips on where the skirt should end on the leg and also for the type of top to wear. I recently wore a midi skirt and realize now that the top was too long- it just didn’t feel right.

    1. This top would have been too long on me too so I folded the hem up and under. Proportion is so important for us petite ladies.

  19. I do alter things! I hem pants and skirts. I find Chico’s pant have a long drop, so I folder over those waistbands and baste them into place.

  20. I would never guess your outfit came from Walmart! I miss K marts Jaclyn Smith line. Are the kitten heels hard to walk on? They are very cute!

    1. These are very low so quite easy to walk in. They run a big small so I ordered 1 size larger.

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