How to Confidently Wear a Skort Over 50

My foray into shorts territory this spring has me naturally turning to skorts. So many of you have recommended skorts as a comfy option that I thought I’d look into how to wear a skort over 50. I’m delighted to partner once again with Kohl’s and Collective Voice to share a fun skort look in classic neutrals.

What are skorts?

Skorts started as athletic wear but offer so much more for a woman’s summer wardrobe and are a great option for daily wear. They’re a hybrid blend of a skirt with shorts that provide a comfortable, versatile option for women of all ages. Skorts are a great alternative to shorts for women who don’t like their backside outlined in shorts or just want a more elevated silhouette. They’re much easier to move around in than a skirt and protect your modesty while bending over and moving around a lot.

I opted for a neutral look here which can dress up or down with a change of shoes and accessories. This Lands End skort is a pull-on style in a moisture-wicking, wrinkle-resisting fabric that provides UPF 50+ sun protection that’s great for outdoor activities. They come in three colors, sizes XS-XL…the petite option is here, plus size here.

How long should your skorts be?

Skorts come in varying lengths, and you should choose the length that flatters you best and provides the coverage you prefer.

This knee-length skort is 19″ long and has attached shorts with a 5″ inseam. They come right to the top of my knee, which is a nice modest length on me.

woman showing shortys attached to a skort
You can see how long the attached shorts are in this photo.

The shorts attached to this skort are nice and long, so they provide plenty of coverage which translates to extra protection against thigh chafing. The skirt portion is polyester, and the shorts are polyester and spandex, so they stretch with you as you move around.

This Croft & Barrow Skort is 18″ long so my entire knee shows...plus size option here. They come in sixteen colors/patterns, sizes 4-18. They’re also a pull-on style and are made from a cotton/poly/rayon/spandex blend that has a smooth, crisp feel. The description does not list the length of the attached shorts but they also offer thigh chafing protection.

What tops to wear with a skort

Skorts pair nicely with knit tops or tees, and a button-down shirt or blouse. In fact, since the shorts don’t show, you could easily style a skort with a casual blazer for a more polished look.

I opted for a Lands End Sumpima cotton tank that will easily layer under everything. I love that the straps are plenty wide and will cover any and all bra straps. It’s available in ten colors, sizes XS-XL Tall. The scoop neck is shallow enough to maintain your modesty when you bend over…always a plus in my book.

black and neutral skort outfit on woman over 50

I I topped the tank with this Nina Leonard crocheted cardigan that dresses the look up a teeny bit…plus size option here. This cardigan is slightly cropped, so comes just to the waist and doesn’t overpower the skort. It’s available in five shades and is selling out fast! This is a great little cardi to go over so many things for a bit of arm coverage this summer. I opted for black to give a longer line with the skort.

Shoes to wear with a skort

Skorts look great with tennies and sandals of all heel heights, but I would skip the stilettos :). I’d beware of wearing a skort with ballet flats because they can tend to look heavy and potentially stodgy. Lots of summer wedges have ankle straps, but I chose these peep-toe Lifestride wedge sandals without an ankle strap to help elongate the look of my leg. They come in five colors, including taupe, which would have elongated my leg even more.

My Vera Wang straw tote comes in black and natural, black and orange, and all black. I chose the two-tone with natural because it’ll go with more things and is perfect with my wedge sandals. It has a removable and adjustable crossbody strap and is made from durable paper straw.


Kohl’s carries an exclusive selection of quality merchandise from brands you know and trust. They’re famous for their amazing sales and deals that save you money on everything from women’s fashion to elevated home decor. You earn $10 in Kohl’s cash for every $50 you spend and you can also earn an extra 35% off when you apply for Kohl’s Card. Take an extra 15% off one time only, off your next online purchase when you sign up for mobile sale alerts.

A skort can be dressed up or down to fit your style esthetic and are a cool option for busy summer days. Do you wear skorts?

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


  1. I never wear skorts. I have very wide hips and shoulders so all that cloth jusrt makes me look even larger! And adding another layer here in Florida is just awful! But you nice in all of them.

  2. Skorts are great and I love the black and white outfit on you!
    I have skorts in navy, black and red. I purchased them a long time ago from QVC; Susan Graver line. I think she still features some.
    I never wear them until I’ve used self-tanner on my legs! That seems to diminish the “shortness” a bit and makes me feel more comfortable baring my legs.

    1. I rely on self tanner too

  3. I finally found a skort where the shorts were long enough to stay put on my thighs. Chico’s! But the skort is 2 inches above the knee on my thunder thighs. Is that an appropriate casual look for a “mature” woman? TIA

    1. I think that’s totaly approrpiate! Women our age wear shorts much shorter than that.

      1. I mistakenly pressed Done while I was still drafting my post. For skorts, I like these brands: Title Nine (for prints), & EleVen (for black). I wear the skorts with tank tops (grey, black or a color) under a white long sleeve shirt. They work well in the hot Texas summer. Susan

  4. I wondered which size you selected on LandsEnd skort? Some say size down in reviews. Wondered what your experience was on size as it looks like a good fit for you. Thanks for reviewing. Had never considered before!

    1. I’m wearing the small. I try to list all sizes below the pictures. I do think it runs large so you could size down.

  5. Made a run on every style of skorts that Kohl’s is selling last week. 😀 And I LOVE them! They were priced right and so comfy. I also love your styling ideas and have made notes – pinned to Pinterest! Mine are also washing well so far which is good to know. I’m glad that skorts have made a return to summer fashion.

    1. Thank you for sharing to Pinterest, Pam! I really appreciate it.

  6. My ideal skorts will be as long as pants. In fact, they will be pants. I don’t enjoy spreading sunblock all over my legs, and the quality stuff I need is expensive. Plus, it tends to stain and ruin clothing. Even my summer skirts and dresses are long, for this reason.

    1. Fabrics with UPF50+ are so helpful!

  7. Pat Patterson says:

    Good morning Jennifer, from the Rocky Mountains in Colorado.
    The featured outfits are so fortuitous, I just bought 2 skorts from Talbots and the lifestride wedge shoe.great choices😍
    Have a great day!

    1. Good morning Pat!! I love a low wedge for comfort 🙂

    2. I use to love skort when they first came out. Guess I need to try them again.
      Thanks for more great info.

  8. You look great in skorts Jennifer and I love the black & white outfit.
    I have 2 pair of 19″ golf skorts (which seems to be the longest manufactures make) which end a few inches above my knees.
    I would love to find a 20″ or 21″ length which I would feel more comfortable wearing off the golf course.

    1. I will keep an eye out for some longer ones. Often buying “talls”, will get you a an extra inch or so.

  9. Mary Frances says:

    I love skorts. I have several, but I prefer the 20″ length to cover my whole knee. They are so easy to wear and look a bit more “dressed” than shorts. There are lots of styles available if you let Google find them for you.

  10. Christi S. says:

    I remember when skorts first appeared many years ago (20+??), they were a skirt front (panel) and shorts in the back – awful! I like how they have evolved and will try them. Thanks for a great post, Jennifer.

    1. I rememeber those too. Perhaps that’s why I never investigated them further

  11. You look so polished in the first image with the black and white with wedges and straw/black bag. That definitely expands my ideas about skorts! The sweater looks great and helps to make that outfit. Black and white aren’t great for me, but I love the classic, polished look it gives.

    1. The cardigan and skort also come in other colors. You might like the navy.

  12. Jennifer I really really like this black skort on you! I have a black one that I wear at the cottage and find it much better for me than shorts! I am not as slim as you and you can wear shorts easily!
    A skort covers up better and I feel much more comfortable and confident wearing it.

    1. I think I like them better than shorts too!

  13. Shellia McCormick says:

    Thanks so much for this post in particular. I have two skorts, but I never though of dressing them up. One’s denim and one is sort of a blue and white striped soft cotton; I think that one could be dressed up. I’m planning a train trip/vacation soon and now I have some great ideas. Thanks, again

    1. Yay! I’m so glad this gave you some ideas. Have a great trip.I love trains.

  14. Charlene J. says:

    Thank you for including your plus size readers. I love the Talbots Washed Linen Jacket; however, the turquoise is sold out in my size. I love reading your blog whether or not it includes plus size. It still gives me ideas.

    1. I will try to include them whenever I can! I know I have many plus size readers.

  15. I LOVE skorts, and am pleased to have them move off the golf course and into “mainstream” summer fashion. Thank you for featuring them.

    1. They’re really a great option!

  16. I wear skorts, and love them as an alternative to shorts in the summer. While I wear mine mostly for walking and hiking, I will now consider dressing up a skort for other activities! I have not tried either brand you feature (I am addicted to Patagonia skorts), but I like all of your options!

    1. Thanks for letting me know about Patagonia! I’ll check them out.

  17. A great post Jennifer! I’m glad you tried skorts. I basically wear skorts all summer long. You are right about shorts and the backside, that is my primary reason for choosing skorts. I find I can dress them up with a nice top and completer piece and cute sandal or go very casual with flip flops and a tee. I have, also, found more choices in more stores of late, so skorts are catching on.

    1. They’re super popular! I’m glad I found them.

  18. You look great in skorts. You look cool and summery. I say, if you have the legs, go for it. Sadly I don’t.

  19. Elizabeth A says:

    I have tried so many times to wear a skort, but I just don´t like the look on me. I have the hanging apron, and they are tight around the lower abdomen. They are more than looking tight, it follows the lower curve of that hanging area (C section and weight loss surgery hanging apron).
    Instead I wear very thin shorts under a casual skirt. (my favorite for this are the Rio shorts from a relatively new woman´s owned company online only Senita Athletics.)

    1. That sounds like a great option for you. I know all styles aren’t you every women. Your work-around sounds perfect.

  20. Joann Czarny says:

    The only skorts I have are from Amazon and they feel more athletic in nature to me. I am tall, so a 25” inseam is knee length and this is what I would search for, if they even exist. I am always on the lookout.
    I like how you have them styled in your post today.

  21. This was enlightening for me. I didn’t realize Kohls even had Skorts. They are all so cute! I really only wear them golfing but now I see how they can be worn as a skirt also, not just for sports. I’m going to be thinking about other options now.

    1. They’re a great option for every day wear, depending on the detailing.

  22. I love this post! Skorts look like the perfect option for me – I do love that you’ve dressed up the outfit. And I appreciate the advice of wearing just a little wedge shoe to lengthen the legs.
    Thank you, Jennifer – I’ll be heading to Kohl’s soon.

  23. Thanks Jennifer for this post… you look awesome…I am wearing a land’s end skort today with a white eyelet top. I have many skorts from Kohls as well. Skorts as you said are a versatile style …stylish as well as comfortable…

  24. I’ve been wearing skorts for years, my preferred brand is Athleta. They have many lengths, are size inclusive, but most importantly for me they have a lot of useable pockets! I wear them as I would wear shorts, so lots and lots of outfits with sneakers, flip flops and casual sandals.

    1. Another great brand to check out!

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