Midi Skirts Are Having A Moment

I tend to love long or short skirts but the truth is, I’m finding mid-length skirts are easier to wear. They cover a multitude of sins (I’m looking at you, aging knees) but will give you lots of options.

This month Cindy and I are thrilled to be joined by our incredibly chic friend Vicki, to talk about skirts. You may remember, I raved about Vicki’s brilliant little book.

fashion blogger Jennifer Connolly wearing black top and pink midi skirt

Midi skirts flatter all figures and are a great piece to dress up or down. They are a graceful look for many occasions. They look wonderful with heels, flats, and even knee-high boots. As with all dresses, skirts, and crop pants… they are most flattering when they are hemmed to a spot where your leg narrows.

Also – How to Look Taller and Slimmer

over 50 fashion blogger Jennifer Connolly showing how to style a midi skirt

They’re modest yet feminine, without being too girly. Midi skirts are easy to walk in, and comfy to wear. They’re best worn with a shorter or tucked-in top to lengthen the look of your leg and give you a flattering proportion (1/3 – 2/3 ).  A nude or your skin color shoe will help elongate your leg which makes you look taller.

Also – How To Wear A Midi Skit

If you don’t like to tuck in your top, try a shorter top or a sweater that stops at your high hip level. Another option is to wear a longer third piece open over the top and skirt.

I ran across this skirt in Nordstrom last week and absolutely loved it! It’s a great addition to my wardrobe for now and into the fall. It comes in several prints but this rose color spotted pattern spoke to me. It has an animal print vibe in a cool tone which as you know, is a favorite for me. It is classy and elegant, but fun and different.

I love the idea of wearing a midi skirt with a simple cotton tee and some easy sandals for now… then styled with knee boots and a cashmere sweater for fall.


Let’s go read what Vicki Archer and Cindy Hattersley have to say about skirts. I love being inspired by other women’s creativity and style, don’t you?


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  1. The skirt is very flattering. I don’t care for black worn near the face as we get older..it really tends to drain us. The black boots look a bit too heavy for the fabrication of the skirt. I think a light coloured top and a pair of more feminine flats would work better. A metallic or clear acrylic framed pair of sunglasses to blend with your hair colour would also soften the look.
    I enjoy your blog and hope to see more outfits as you move towards Fall in the Northern hemisphere. Here on the Eastern Coast of Australia we have enjoyed a mild Winter and have been wearing a lot of longer skirts…as I get older I think the longer skirts work well and are more flattering than a shorter pencil or fit and flare style.I have a few Summer dresses in this length ..they are cool and comfortable in the hot tropical weather that will be creeping up on us soon.

  2. Midi is my favorite length for all year round, with boots, booties, sandals, you name it. Of course there are some for winter, and others for summer. I thought I couldn’t wear pleats until I tried a midi with relaxed micro-pleats. I changed my mind. I have the height to carry it off.

  3. the boots are too clumsy to that skirt also for shirt and boots are the color too dark. Otherwise
    I agree what you think about midi or long skirts.

  4. What a great look for you! I have not worn skirts or dresses for years. No capris or shorts either. Unfortunately, my legs goes straight down to my big veiny ankles, and I’m only 5′-1′. AAGH! Maybe I could try a maxi with boots this winter. Love your blog!

  5. I love the longer length. The trick is to find the sweet spot on your leg. Most women would look a lot slimmer by covering their knees. You look lovely in this skirt.

  6. I love skirts and think that midi looks beautiful on you – it goes so well with your skin color. I do prefer maxi length for myself in both skirts and dresses as I like the swish around my feet and it’s more dramatic and consistent with my boho vibe, but the midi can be very elegant.

  7. You are so right about the correct length is usually where
    the hem hits you at the most flattering part of your leg. This goes for pants. I think a lot of women try on clothing items and say “too dowdy” without trying to look at length.

  8. You look fabulous!! I love the skirt on you. I’ve always been afraid of wearing one but, maybe I’ll try one on now!!!

  9. My fav length is ankle/opera length!
    Love seeing how you styled the outfits. You are the bomb of getting it all together!

  10. I love a midi if it is long enough to cover all “the sins”. Most midis end up being maxis on me as my legs are short! You look great in that blush pink, and I love the pink and black combo. Great post as always!!

  11. I like mid-length in some dress and skirts. As for the small pleats — “Oh, Heck; NO! Don’t like the funky style boots — its looks dorky.

  12. I like that length skirt. Because I’m so short that’s where they usually end up anyway. I find I usually have to wear some kind of heel to not look frumpy!

  13. I have been wearing midi- skirts for a long time. They are feminine, can be dressed up or dressed down, and can be worn with any type of shoe.
    It’s a great look on you. I like the contrast of the pink print skirt and the black blouse/ sweater. Very feminine and pulled together.
    Have a great day!

  14. Once again, you showed us how to create a feminine, classic, easy to wear look that so many of us could duplicate. Your confidence level is off the charts in these photos! I love the mix of colors and accessories that compliment this look.
    Frankly, I have no need at this time to add a new skirt to my wardrobe. I am just adding an occasional new, basic piece to my existing closet. However, I love to see what’s new and dream about a time when I did wear these outfits or when I might have the opportunity again.
    Thankyou for keeping us current Jennifer!

  15. The skirt looks nice. I have been wearing this length for years! It always looks good and any shoe / boot works. I recently cleaned out my closet and this length skirt and longer made the cut while shorter skirts did not.

  16. Jennifer… I love you in the pink and black combination… it looks wonderful. I am a fan of the midi too.. and they are really perfect in all seasons. xx

  17. Great look on you and I really like the colour. I agree with the length, if it is not at the right spot it can look all wrong and I have adjusted many of mine. i wear this length most of the time lately and have gotten rid of my knee length ones for the most part. It looks like you are purchasing most of your new items in the summer catagory. Have you settled on a system that feels right for you? I like the colour of the shoes, but I don’t seem to be able to wear mules or slides. I had an unfortunate incident with slipping sideways on stairs and that is it for me.

  18. Definitely one of my favourite lengths and looks in a skirt ( and not to be confused with a maxi) as feel no matter their fabric; are elegant and graceful in appearance. Love their versatility for all seasons however during the Fall or Winter often pair them with knee high boots or colored tights and/or stockings sometimes if wearing just a shoe. When topping off with a jacket ; prefer that which hits ‘no lower’ than the hip unless I wish a very casual look then may opt for an over sized sweater or some type of wrap/poncho. Do love the look on you Jennifer!
    Footnote: I live in Canada (in a snow belt region to be exact) so our seasonal temps can vastly differ from our neighbours to the South of us.

  19. I hardly ever wear a skirt. I usually wear capris or shorts here in Florida. You do look very nice in that skirt!

  20. What a pretty skirt. I love the look with the classic v neck cashmere sweater. This would look cute with black loafers as well. Very femine but classic.

  21. Except for Talbots newest jean skirt (I bought a petite in my size) I don’t wear skirts much anymore. I do own some beautiful flowy palazzo pants in Tencel blends, even linen blends that resemble long skirts for evenings out.
    My idea of midi is mid calf And unless it’s a winter weight and I can wear tall boots I avoid this length.
    In retirement I’m just not going to wear such styles—cannot justify their cost.