An Easy Way to Style a Tweed Skirt

Hey guys. Don’t fall of your chair or anything, but today I’m styling a skirt!

an easy way to style a tweed skirt | black jewel neck sweater, over the knee boots, structured satchel

My biggest struggle with skirts is not finding ones I like, but finding a top to wear with them. I prefer a shorter top with a skirt to balance out the proportions, and shorter tops haven’t been very popular in recent years. I see other girls doing the front tuck with their skirts, but it looks a little off when I try it, so I’ve gone without wearing skirts for a long time. That said, I’ve been wanting to incorporate a few skirt outfits into my winter wardrobe, so I set out to find one that works.

You may remember this tweed skirt from Ann Taylor in my January Wish List post. I immediately fell in love with the gorgeous tweed so I took a chance and ordered it. Now that higher rise jeans are coming back in style, tops are getting shorter, so I was able to find a the perfect sweater to pair with this skirt!

Winter Tweed Skirt Outfit with OTK Boots

An easy way to style a tweed skirt is to wear it with a black top and tall black boots. Tights are optional. 

You really can’t go wrong with this outfit formula as long as each piece fits well so the outfit creates a pleasing proportion. You can see in this look that my body is pretty divided evenly into thirds, with the tweed skirt providing a nice contrast between the black on top and bottom.

I was so pleased to discover this sweater. I really like the quality, and the wrist detail is nice. A jewel neck isn’t my first choice of neckline, but it fits everywhere else and works with the skirt so I can make do. I compensated for the high neckline by wearing a long pendant to visually elongate the upper body and draw the eye in and down towards my waist.

Easy Way to Style A Tweed Skirt: black jewel neck sweater, over the knee boots, structured satchel | jolynnedev.wpenginepowered.com

Unfortunately the sweater low inventory but it does come in several nice colors if you can find your size. Other good options include this pointelle turtleneck, this button sleeve sweater, and this lantern sleeve ribbed sweater. They all have a classic fit that works well with skirts and are around the same length as this sweater, which is 23.5″.

SALE ALERT >> 50% off your purchase at Ann Taylor with code GETWARM.

A chunkier sweater could also work with this look, but I feel like this dressier fine gauge knit is more flattering for my body type; my waist seems to get lost when I try to pair a skirt with a chunky sweater.

I really like the color palette in the skirt and the subtle a-line shape. I also like the button detail on the waist and hated to cover it up, but I’m too short waisted to tuck in my tops. For size reference, I have a small in the sweater and a 6 in the skirt.

I went with silver accessories, but gold would certainly work as well.

Ann Taylor Button Cuff Sweater

The over the knee boots work well with this, but knee-high boots work just as well if that’s more your style. With OTK boots, I like to see an inch between the top of the boots and the bottom of the skirt, but in this case mine almost meet in the front, and I guess that’s okay. Sometimes I wish I were one or two inches taller.

Pumps or ankle boots would be a good alternative to the OTK boots if you need more conservative footwear. You can go with a lower heel too; my boots just happen to be heels.

I added my leather jacket on top to give the classic outfit a bit of an edge (and for added warmth.) If you work in an office, you could easily do a blazer (or go without a top layer.) For size reference, I have this jacket in a medium.

Easy Way to Style A Tweed Skirt for Winter: black jewel neck sweater, over the knee boots, structured satchel | jolynnedev.wpenginepowered.com

My R Minkoff Mini Perry Satchel is the perfect accompaniment, with its silver hardware and structured styling, and it’s currently 50% off! The price on this bag fluctuates a lot, but this is the lowest I’ve ever seen it. I think I snagged mine when it was around $215, and today it’s $191 plus it’s Amazon Prime.

Overall I’m really pleased with how this outfit came together. I can definitely see myself wearing this to church or out to dinner with my husband sometime.

Winter Tweed Skirt Outfit with OTK Boots | R Minkoff Mini Perry Satchel | Ann Taylor Button Cuff Sweater | jolynnedev.wpenginepowered.com #fashionover40 #winteroutfit

AT button cuff sweater // AT tweed button tab skirt // leather jacket // similar boots (optionoption) // tights // bag // necklace // link bracelet

photo credit: Alison Cornell

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45 Responses

  1. Love this! I rarely wear skirts or dresses (a little more in warm weather), but when you originally posted the link I whipped over to Ann Taylor. Sadly (or maybe fortunately) by then, my size was no longer available. The whole outfit looks wonderful on you!

      1. Boo… Just checked it out. I would prefer the petite length (I’m 5′ tall), but I’d get the regular if necessary and get it hemmed, but unless the sizes run really small, they don’t have my size. ☹️

  2. Yes, I did almost fall out of my chair!  This look is so different for you, and I LOVE it!  You look amazing! I love that tweed skirt with those boots. So chic!

  3. Well done! If I were still working in the business world, this would be an outfit I would wear. I love the details on the black sweater sleeve. 

  4. You look fantastic! It really is difficult to find basic and fitted v-neck sweaters.  I used to have a few and would wear them with a trouser pant and a cute heel but most sweaters are so long and bulky now …which is okay except for when you really could use a more tailored/fitted one. 

  5. I love this outfit , l really like the colors in the skirt . I said I wasn’t going to buy anymore clothes until I went thru the Adore class but this is very tempting. I usually don’t wear skirts because I haven’t found one that I like but I have now . Thanks for the inspiration.
    Have a great day !!!!

  6. Not only fell off my chair but gasped in delight, Jo-Lynne!!
    This look is so incredible on you….you look like you stepped out of a fashion magazine!!
    I think you need to recreate this every week!!
    Love, love and love it more!!

  7. Love the outfit – if you wore it with pumps what would you wear on your legs? Do black tights go with pumps?

  8. Love, love, love this outfit!! You look amazing in it!!

    I bought my first Ann Taylor sweater at the mall earlier this week, a striped peplum (because #stripes!!) If it weren’t for you mentioning them in a couple posts recently, I may not have looked there. 

  9. Love this skirt!!  Here’s a suggestion– while my initial way to style it would be with black top and black tights/boots Luke you did,  it would be really pretty if you could find a sweater the same color as that light blue thread!  Love the way you styled it here too 

    1. I was thinking that pulling out a color from the skirt would be a nice alternative. Funny, I was thinking the pink, but I was afraid it would be too bright. I like the idea of the light blue even better.

  10. I really appreciated how you broke down this outfit ,and wrote about proportion. Pointing out that the outfit was basically divided evenly into thirds was very helpful in figuring out how to wear a skirt well. I am very high waisted, so I find skirts tricky. This post made it seem doable. And you look so fabulous, edgy and not stuffy at all!

  11. You look FABULOUS in this outfit Jo-Lynne!  I see you getting a lot of wear out of the skirt and sweater.
    Have a fabulous weekend!

  12. Looks great on you!  And the boat neck looks great too, even though I know you prefer V-necks.  Switching it up at times keeps things from getting boring and expected. 

  13. Love the look on you, and I also love the discussion of WHY it works AND lots of alternatives for footwear! You knocked this one out of the park!

  14. Thanks for this. I have a tweed skirt that is brown/tan with black and copper accents. I was not sure what to pair with it. I think I will focus on the black since I have similar boots and will only need a fitted black top.

  15. I was thinking of wearing something similar to church Sunday but my skirt is diagonal print. But was not sure about boots so to see you in boots with heels confirmed that I should do that instead of flat boots. Mine are to the knee though. Like you I seldom wear skirts or dresses so this was a perfect post today for me. One question. I usually buy jeans in sizes instead of waist. I saw some online and not sure if I should get 27 or 28. I wear a 4 in some and 6 in other brands. Any suggestions?

  16. I’m loving this outfit. The length of the skirt is perfect, the sweater has beautiful detail and the OTK boots & leather jacket  lend a younger, edgier feel. You nailed it! 

  17. I haven’t read your post yet because I want to tell you before I get distracted by life – you nailed it with this outfit!! Awesome !! Ok back to reading the your post. Lol

  18. Great looking outfit and fantastic sale.  The matching tweed jacket is also awesome!  Unfortunately, the heel on the boots is too tall for me, but I love those too.

  19. I keep thinking I’d like to add a skirt or two to my closet too, but I swear even with the shorter sweaters, I’m so short waisted I still don’t like the look on myself. Love this skirt and the way you put the outfit together. The details on the sleeve of the sweater are really cute. Adding the leather jacket was a nice touch to keep it from being to “conservative”???? Happy Friday Jo-Lynne. Hope you get a little reprieve from the cold and a warmer run soon! XO

  20. This is perfect …. Love it!!! Just walking in the room gains you respect with this outfit you definitely impress when you are wearing something like this!! You just took it to the next level!

  21. Wow, this seems like such a different look from your usual, but you look absolutely fantastic in it! Funny, when you were talking about trouble finding shirts for skirts at the beginning of the post, I was wondering why you don’t just tuck some of them in, and then you explained why you prefer not to do that. Always informative and that’s one of the many reasons we love you!

  22. I know from your blog posts that you have been through the AYW courses. I am a #shortwaistedpear#cool and have had a frustrating time finding tops that fit the rules. I’d love to see a blog of outfits for a pear shaped person—bootcut jeans and tops/sweaters that fit the “bring the eye up and out” mantra. Tops and sweaters are often way too long to fit a shorter SSR, have a shirttail hem instead of straight, or boob pockets or are oversized and look more like tunics. Any wisdom to share? Do you have a “pear” friend who would model for you? 

    1. Hey Kate, I also have a shorter SSR so I’m happy to see shorter tops trending. I’m #shortwaistedcurvy #cool in case you didn’t already figure that out. 🙂 When friends ask me to style them, I always joke that I can barely figure how to dress myself, but it’s really true. I feel like I’m just getting the hang of the curvy rules so I don’t really keep track of the other body type rules, and I don’t have any friends interested in modeling for me, although that’s a cool idea.

      Hopefully the outfit ideas, color combinations, current trends, and feedback on sizing that I share are helpful for all body types, and then modifications can be made to work for each individual person.

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