Flannel Pencil Skirt & Moto Jacket

Good morning! I hope you’re sitting down because I have… wait for it… a skirt outfit today!!!

Fashion Over 40: How to style a pencil skirt with a moto jacket

I know. This is unprecedented. I don’t think I’ve styled a non-denim skirt on this blog in years, and that is no exaggeration.

It’s not that I don’t like skirts. I’m a huge fan of a good pencil skirt, and I used to wear them a lot in the early 2000s. Sweater trends were shorter back then, and it was easy to create the proper portions with a pencil skirt. I’m not a tucker-inner because I’m too short-waisted for that, so now that longer sweaters are in style, it’s really hard to find the right top to pair with a pencil skirt. I see women doing the front-tuck with their skirts, and I think that looks all kinds of wonky.

Thankfully, shorter tops seem to be coming back in style, and one of the best stores I’ve found for more traditional sweaters is Banana Republic. I’ve bought several of their sweaters this winter, and I’m very pleased with them. They’re still long enough to create the right balance with skinny jeans, but they’re short enough to work with a knee-length pencil skirt.

Fashion Over 40: How to style a pencil skirt with a moto jacket

This one is my new favorite — it’s a simple black fine-gauge, ribbed-knit scoop neck sweater. It comes in 4 neutral colors, and it has a lovely fit and feel. It’s a nice, soft knit that feels good against the skin. I wore it with jeans to dinner last weekend, and then I paired it with this wool pencil skirt for a dressy work wear look that would also be nice for church. For size reference, I’m wearing a small in the sweater.

Fashion Over 40: Flannel Pencil Skirt & Moto Jacket

Unfortunately, the skirt I’m wearing is sold out. It’s also from Banana Republic, and I waited too long to style it. I was actually waiting to find a sweater that would work with it. They do have a lot of other skirts to choose from, though.

Fashion Over 40: How to style a pencil skirt with a moto jacket

I tried wearing my black over-the-knee boots with this, but they were too tall. They touched the skirt and didn’t allow any leg to show, so I went with suede pumps. A knee-high dressy boot would work, but I don’t have a pair at the moment.

These tights are black, but the way the light is shining on them, they look a bit off. In real life, they’re very black. These are the Spanx brand, and I love them. It’s the only brand of tights I wear. They’re nice and opaque and they hold everything in place.

Fashion Over 40: Flannel Pencil Skirt & Moto Jacket

I topped off the outfit off with my coated cotton moto jacket. I like the structure it adds to the outfit, and it also give the look a bit of an edge and keeps it from being too classic. I wouldn’t need the jacket as much if I were wearing over-the-knee boots or booties, but with the pumps, this outfit could look a bit dated or too safe, so the moto jacket helps keep it current.

Fashion Over 40: How to style a pencil skirt with a moto jacket

Fashion Over 40: Flannel Pencil Skirt & Moto Jacket

Fashion Over 40: How to style a pencil skirt with a moto jacket

Finally, this necklace is Stella & Dot. I really liked the way it fills the neckline of the sweater, and the gold creates a pretty contrast against the dark color palette of the outfit. It also draws the eye up towards my face because it’s lighter/brighter than anything else I’m wearing.

Fashion Over 40: Flannel Pencil Skirt & Moto Jacket

The only exception to that statement is my purse. I intentionally carried a black purse with gold hardware to coordinate with the necklace and to offer another point of interest to the outfit.

Fashion Over 40: How to style a pencil skirt with a moto jacket

Shop the Post

scoop neck sweater // similar flannel pencil skirt // similar moto jacket // spanx tights // similar pumps // shoulder bag // necklace

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23 Responses

  1. Great look! Thank you for the tips. So very helpful. I could not figure out why I couldn’t make pencil skirts work for the past few years. I’d put an outfit together & look matronly, shapeless or complletely out of proportion. Now I have the ammo to try again. Including taking a look at Banana Republic sweaters.

  2. Ahhhh, Jo-Lynne, you look like a vision of loveliness in that skirt!! You know I’m a sucker for skirts & dresses, so this outfit put a smile on my face!
    And pairing it with the leather jacket is what I consider perfect!
    I have a quandary though?
    One of the reasons I love my OTK boots is exactly the reason you gave for not wearing them. I love that they fill the gap between skirt & boot and therefore create a longer line. How come you didn’t like that?

    1. Like anything else in fashion, an inch can make all the difference, and in this case, the boots and skirt just met, or the skirt may have even overlapped a bit, so it buckled when it hit them just right as I walked. I think you really need at least an inch between OTK boots and a skirt to allow for ease of movement and to look right. I actually like to see a bit of leg between the skirt and the boot; I think it’s more slimming that way, plus the black tights keep that long, lean leg line.

      Also of note, my boots are leather, so they’re not snug to the leg, and they caught the skirt in them as I walked. If I had those gorgeous Stuart Weitzman suede OTK boots that are snug like leggings, with the tie in the back, it might not matter if the skirt came down over them a tad.

      So many details to consider! LOL

  3. Love this! Totally a work wear outfit that I would wear. Agree it’s hard to find tops with skirts, but I do like them. I’m finding the hem length also to contribute to the frumpiness at times. I just decided this weekend to take a couple of mine in and get them shortened and inch. I think I’ll wear them more. I am going to have to check out that sweater. Love it.

  4. This is a great post! So many helpful hints I love everything about this outfit and will definitely be looking at Banana Republic. I love skirts, thank you so much for the post it made my day ????

  5. Love the outfit. And hurray for shorter tops and sweaters! I completely understand why we want a longer top sometimes. What I don’t understand is why where there’s a trend, companies make ONLY that style. I almost always look better with a shorter top. I have long legs, short waist (or no waist anymore, lol) and a large bust. Long tops generally make me look like I’m wearing maternity clothes! (Minus the baby belly!)

    Happy Thursday!

    1. Yes, yes, and yes. To all that. I have the same figure shape (as you probably know, haha!) and I don’t know why designers can’t make a variety of lengths. Now the cropped sweaters are coming back, but they’re almost too short. I wish we could find a happy medium again.

  6. Loving this outfit, and as always, you look stunning! I wore this exact skirt to a Christmas party. I styled it with a 3/4 sleeve ivory lace top, dressy high-heeled booties, and black opaque tights. The contrast between the texture of the skirt and the feminine top made it fun. Thanks for giving me style options with this skirt! I love the sweater you are wearing! The scoop neck is so flattering on every body type. BR has really put out some beautiful, quality sweaters lately.

  7. Jo-Lynne, I have been following your blog for a few months and I wanted to let you know how much I enjoy it. Hubby and I recently retired and moved at ages 61 and I found that my wardrobe no longer seemed to work for me. What I especially like about your blog is the down to earth style inspiration. You present excellent formulas for casual, but polished everyday wear with the occasional dressier outfit such as the look you are styling today. Your ideas sent me back to my closet to rethink what I already own….and on a couple of fun shopping trips to add a small number of pieces that have dramatically expanded my outfit choices. I don’t add pieces just because they are in style…I just can’t bring myself to try ripped jeans or OTK boots…but your suggestions and ideas have inspired more than one aha! moment on how I could update my look and still feel like me. Great job! Thanks for an always fun morning virtual visit! Ps…I live in Maine and I was so relieved that you had Mom’s boots to borrow when you were here for your grandfather’S party. Caught a glimpse of you, too in the BDN photos.

  8. Very cute outfit on you Jo-Lynne. I too love the look of a cute pencil skirt, but rarely buy or wear them for some reason. I tend to wear skirts more in the summer…..casual ones. At age 55, I’m not that comfortable in shorts. 🙂 Probably because the legs need a work out. 🙂 Your hair looks really cute and you curled it just perfect. 🙂

  9. I was looking at the tights on the Nordstrom website and it said to refer to the sizing chart to select the right size. But I couldn’t find the Spanx tights chart anywhere in the details below the picture. Can you help with what Spanx letter corresponds to what size? Thanks!

      1. I was on that page but was on my phone and could only see the letters. I’m at my desktop now and can see the link right below those. Thanks! 🙂

  10. Oh, I love this outfit! Pencil skirts are so classic, and classy. I love the way you’ve styled this.

    I appreciate the heads up about Banana Republic. I’m always on the lookout for shorter sweaters and tops. My daughter wears BR clothes, and she praises the quality.

  11. I think most of my shorter tops ive had for a long time. My hips are large enough that if a top is longer i need to go up a size or it’s too tight at the bottom. It’s making shopping for shirts almost as difficult as pants. Ughs.

  12. Hi Jo-Lynne,
    Lovely look! I agree what pulls it together is the leather jacket, otherwise it would be elegant but without an edge, and your style is edgy/trendy! I’m so pleased as I bought a very similar skirt that was pricey, but I ended up never wearing it as I just looked too conservative and 15 years older than I am. The leather jacket just nails it. Sadly, I don’t have one -yet! I’ve been wanting to add one to my wardrobe for ages, now I have another reason! Lol. Thanks for keeping me from donating my skirt, now I know how to style it.

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