How to Style a Maxi Skirt

The maxi skirt is a look I admire on others but never felt that it would work for me; I’m more of a pencil skirt kinda gal. But I recently bought my first maxidress (I KNOW!) and I have enjoyed it so much that when I came across a rack of maxi skirts at the Gap last week, I impulsively decided to buy one. It seems like a versatile, casual summer piece that could add some variety to my wardrobe.

A maxidress is easier to style because you already have the main component of the outfit in the dress. I am finding it a bit more challenging to style my new maxi skirt because I have to figure out what to wear for a top before I even get around to accessorizing. Of course that warrants a post about it!

My skirt is a basic black cotton knit. I had envisioned it with a tank top and flat sandals. For some reason, in my mind, maxi skirts and tank tops seem to go together. So I went through my closet to see what I could find.

Take One: white tank, jean jacket, pink sandals and accessories

My first attempt was totally NOT WORKING. The top is way too long and makes me look boxy. Bleh. The denim jacket adds some much needed structure, but the tank is still too long, and I would want to be able to remove my jacket. Pants that button are so much more forgiving than a skirt like this. It shows every imperfection, which is why I have avoided them for so long. So far, this outfit is a big, fat NO.

maxi skirt with white and denim

Take Two: floral tank, denim jacket, silver sandals and accessories

The next way I tried it was with this floral tank. I actually ended up wearing it this way to visit my friendly endodontist (root canal #3 coming up . . . sigh) which was okay as long as I kept the jacket on, which I did. Without the jacket, the tank is too tight for my comfort level, and I’m not sure I like that much of the print. This could be cute with a chambray shirt over it, knotted at the waist.

maxi skirt with printed top

I was feeling dumpy in the long, flowy skirt so I tried it on with heels.

maxi skirt with heels

Better, but dressier than I wanted to be. Plus I really want to be able to wear the skirt without the jacket so I knew I needed to try something else. This could work though, for a casual dinner.

Take Three: teal tissue tee

The next top I tried was this teal tissue tee. It’s not as tight as my tanks, so I thought perhaps it would work better, but I just felt dumpy. Maybe if I had a wide belt that I could wear over the shirt, slightly below the waist . . . but I don’t.

maxi skirt5

I was thinking at this point that the skirt could be cute with a fitted blouse. There are a lot of pictures on pinterest of maxi skirts with button-down blouses tied at the waist, or with a belt to provide some definition at the waist. But I’m bound by what I have in my closet and I don’t have any button-down tops or sassy wide belts. I also don’t think the skirt would work for me with something more blousy. I tend to feel thinner in tops that are more body hugging or structured.

Take Four: orange tank with a statement necklace or . . . a scarf!

Back in my closet again, my eyes landed on this orange ribbed tank. I wear it a lot with skirts because it is a bit shorter than my other tops. I am short-waisted, so I really have to pay attention to the length of my tops. With jeans, I can wear them longer, but with skirts, they really need to be shorter or I look boxy through the middle (see Exhibit A above!) I also like that while the fit of this orange top is body-conscious, it is not skin tight, so I don’t mind wearing it without another layer.

How to Style a Maxi Dress: Tank and Jean Jacket

It’s more flattering than the first attempt, but it’s rather plain. I tried adding a statement necklace, which helped, but it still seemed a little blah. Then I thought about trying a scarf.

Now, you guys know about my love/hate relationship with scarves. I have tried so hard to wear them and like them, but I find them to be incredibly uncomfortable, inconvenient and also just not very flattering on me.


Look how a scarf transforms this outfit.

How to Style a Maxi Skirt: Tank and Scarf.jpg

I really love this look! I tried styling the scarf loosely so it doesn’t look chokey. Of course, this isn’t a practical around-the-house outfit. The scarf gets in the way when I’m doing basic household tasks, but it does finish the outfit if I want to wear it out somewhere.

How to Wear A Summer Scarf

The print and pattern is just what the outfit needed to take it to the next level, and it also helps disguise any lumps and bumps the midsection, where I tend to feel the most self conscious.

maxi skirt with jean jacket and scarf

It looked cute with the denim jacket too, but the jacket AND the scarf is rather heavy for this time of year. Perhaps in the fall, though? With a different shoe . . . oh  no, here we go again! I will save that experiment for another post.

I did end up wearing the outfit with these wedge flip flops. I like the height of the wedge with the casual vibe of the flip flops. I’d probably also like it with the tobacco-colored wedge espadrilles above, depending on where I’m wearing it.

Other ideas . . . a fitted, short-sleeved tee with a sleeveless denim jacket on top could be super cute. And I really do want to try belting it. I grabbed these photos from Pinterest.

How to Style a Maxi Skirt | KnottedSprinkles & Sequins| Belted: Imperfectly Polished | Knotted: Miss Renaissance | Sleeveless Denim Jacket: Neiman Marcus

So many options!

How about you? How do you rock a maxi skirt? I’d love to hear your ideas!


  1. says

    Thanks for this fun post! I do love the look of a maxi skirt (not so much the dress, as they really just seem like moo-moos to me). I don’t know, but maybe your maxi skirt was more difficult to pair b/c it’s a solid black. When you paired it with solid tops, it looked rather blah. It took that GREAT scarf to make the outfit. I agree about scarves and housework. Usually I just wear the outfit sans scarf, and then put it on b/f I go out the door.

    I’m scared of getting a maxi skirt (well, a print one anyway. I have long skirts) b/c I’m heavier. Prints on the bottom half is a massive NO-NO :) But I really enjoyed reading your maxi skirt adventure! I think you’ll learn to love it. Although I must admit: when you do your “pick which of these 5 outfits looks best on JL” posts, I always, always pick the photo where you’re wearing the white jeans. They just look great on you, no matter what else you wear with them. You clearly love your skinny jeans, and possibly the maxi skirt just FEELS odd to you??? It’s a lot of bulk and cover up. I wonder if you’d like one that was more filmy/light weight (like beachy gauze?) in a print? That would be fun!

    • says

      I think if the maxi skirt were a narrower cut, it would be more flattering. I am not as tall as people think I am, and really not as thin either, lol. I carry weight in my middle, from chest to hip, so that’s why I look better in skinny jeans than voluminous skirts. They showcase my thinnest part – whereas this skirt tends to hide my thinnest parts and draw attention to my middle. That’s why the fitted jean jacket helps. And the heels. But I wanted a more casual, easy look.

      I also agree that the solid black looks plain with a solid top. After perusing maxi skirts on Pinterest all morning, I think I’d like to try a narrower cut with a bright chevron print. I think that would be more interesting and more flattering too.

  2. says

    Ok, I love, love, love it with orange tank and scarf! It’s amazing what a scarf can do.

    I picked up a chevron striped maxi skirt at Walmart. Ya, I can’t believe it either, but it was around $10-12 dollars and I fell in love.

    You can see it here, ( ) but I just paired with a longish red top. It’s super-comfy. It’s funny, but for me, I think the skirt is way more forgiving than my pants. I think maybe it’s all about comfort level and for me, I carry my weight in my legs, so skirts really do help me.

    • says

      Yep, see what I just said to MK above. I carry my weight in my middle, so I like things that show how thin my arms and legs are.

      That maxi skirt is so cute! I definitely want to try one with a chevron print.

      • says

        Ya, I read the above comment. I understand what you’re saying. It’s funny how certain articles of clothing totally camouflage certain areas. I’m really trying to learn what works for my body shape, so I don’t have clothes in my closet that I hate. It’s a process. Your posts always help and give me things to think about.

      • says

        I think the wide belt would really help you not feel so boxy. I love my maxi skirts and picked up 2 different wide belts at the consignment store. They totally made the difference in taking the outfit from blah to yeah.

  3. says

    When you asked on fb I voted “yay” even though I’ve never worn one! I think they look adorable on other women but feel like I’d look “frumpy” wearing one. I had pictured you wearing one with a cute print and was thinking this black one just wasn’t gonna work out for you but look how that scarf saved the day! I’m sure you could mix it up with other fun tanks & scarves now that you know that works. Loved seeing the evolution of this outfit. :)

    • says

      Yes, I think I need to find another tank/scarf combo… in fact, I have an idea. I at least have another summery scarf that would be cute, if I can find a coordinating tank top that isn’t too long or too tight, lol. I do need to get one of those sleeveless denim jackets too….

  4. Mandy S says

    That scarf definitely made the outfit! I love scarves. And that one is gorgeous. Where is it from? I want one! :-)

    • says

      LOL. It is from the Banana Republic Factory Outlet and I just got it last week. I came *THIS CLOSE* to not buying it b/c I’m horrible about buying scarves and never wearing them. But the colors were so great, I decided to throw it in the cart anyway. SO GLAD I did!

  5. Lee Ann says

    Wow! What a difference the scarf makes. I like the maxi dress look, but unfortunately, it is not for me. I am 5’2″ and it’s not gonna work! It’s a lot of material for my small frame. I remember the long dress was a style back in the 70s when I was growing up.

  6. says

    Love the orange tank with the scarf!! And really all the looks with the denim jacket. I usually wear mine with either a tighter top and some sort of cardi or button down and I use belts or tie my button downs. Occasionally I will go with just a top but that’s usually only when I’m at home all day. :)

  7. Megan says

    I love maxi dresses (i just bought this one from Ann Taylor which is absolutely adorable – Honestly though, the maxi skirts intimidate me. I tend to carry my weight in my rear and my upper thighs and I feel like the maxi skirt has too much volume in those parts for me. Maybe it’s my height as well – I’m not as tall as people think I am either. :)

  8. Mae says

    I was not sold on you wearing that skirt at all until that scarf made an appearance. You look amazing! I’m glad you kept trying different styles of shirts. I guess I need to be more diligent with trying different looks.

  9. Claudia says

    Try tucking the top in! I love wearing breezy maxi skirts with my favorite tanks ever, my mommy summer uniform, banana republic timeless tanks.

  10. says

    LOVE this post! It is so fun and helpful to see all of the different looks you try.

    LOVE the outfit with the scarf. My 16 year old daughter and I both love scarves, so we have quite a shareable wardrobe of them.

    LOVE, LOVE, LOVE maxi skirts, and have bought several this year. I have never worn maxi skirts before, as they were NOT the right look for a very overweight woman. However, after losing 65 pounds this year, I have been so excited for this new look for me. While I still have weight to lose, and my hips and thighs are where I carry my weight, the loose skirts definitely help to hide the weight (as I continue to diet and exercise). Whereas, pencil skirts and skinny jeans are not working for me yet. :)

    I definitely think you should pick up a wide belt to try. Adding a wide belt to my maxi skirts totally MADE the outfits.

    Loving my maxi skirts . . . with flip flops . . . with dressy sandals . . . and with my new wedge shoes (which were also something I could not wear when I was at my heaviest).

    Love my denim jackets, so will need to look for the sleeveless style (which helps hide my too big chest while I continue to lose weight).

  11. Rochelle Phillips says

    I love the maxi skirt. In the summer it’s easy to throw flip flops on and go but I would love to know how to transition to fall. I have no idea what shoes to wear so I would love to see a post on the shoes!!

  12. Mama Obito says

    I have one white maxi skirt, but I don’t have any courage to wear it yet. I used to have two flower printed maxi when I was a teenager, but it doesn’t fit me anymore. Your different photos in maxi is inspiring me to start over again wearing maxi. Thanks.

    • says

      Oooh Nicole, I love that look of yours – and your skirt is also full. And you pair two solids – but the bright coral is more fun than black, and the statement necklace makes it. But also, you are taller and thinner, and especially slim through the midsection, so you can get away with that longer, tight top where I don’t think I could. Isn’t it interesting how many factors there are in putting an outfit together??

  13. Liz says

    It was great to see you go throught the process of trying on different tops with the skirt as that is exactly what I do except I end up being completely frustrated! You mentioned that you like striped tops in other posts. I was thinking a black striped tank top would elongate your torso but also with a bit of colour. Cheers!

  14. says

    I bought a maxi skirt this morning from a friend who sells Cabi clothes at her sample sale. I also happened to buy an orange top very similar to yours to go with it. I missed this post when you published it (on the day of my son’s high school graduation) but in the back of my mind I just knew it was here, waiting to help me figure this out. I just read it and I’m ready to go. Now I’m excited to try to pull it together and wear out in public. Thanks for always being there to help me figure out fashion Jo-Lynne! Happy Summer!!

  15. Datiyah says

    I recently purchased two maxi skirts – teal green and purple. I have not worn either because I was not sure how to style them. I’m 4’11″, petite and never thought I could achieve this look. You have given me some great ideas for my skirts. Love the bright tank and scarf!

  16. Sockpuppet says

    I wear my maxi skirt the same way with a jean jacket and flat sandals. I’m short, however, and a bit chunky so I wear one color from head to toe. Tres chic.

  17. Mrunal says

    Just loved your experiments with skirt…..and the combo u finalized.

    I am 5’11″ and never thought of wearing maxi skirts…being in love with them sooooo much. And finally i ended up buying a printed black-orange-beige maxi skirt anyway…. that too at the start of the fall. I cant pair it with a tank :( ….thinking of a soft knit sweater in beige or cream. and of course a scarf….loooooove the scarves.

  18. Dee says

    You are way too hard on yourself. You dont look one bit dumpy in any of those pictures. Every outfit looked cute and feminine. Throw on some long beaded necklaces and pretty bangles to help get your attention off of picking on your figure. EX,too boxy,too dumpy ect. You looked pretty in every outfit. Orange and fall colors wouldlook great on you. Your an Autumn.

  19. Leana Jo says

    I’m thinking of changing my way of dressing, now, & this looks like a great idea. I was thinking of wearing long skirts (haven’t in years, now) & didn’t know what kind of shirts/blouses went with them…Thanks for the photos, gives me some great idea when I go shopping the next time. Thanks a million!!

  20. says

    I really like the way you walked us through each outfit and why it worked and didn’t. I am in the process of trying to figure out what to wear for a christmas party. I have a long black skirt, but also a maxi striped dress. I am going to wear the dress (like the stripes) with a black button jacket or black cardigan, with either a bunch of necklaces or a scarf. I do like your pop of colour with the orange tee!

  21. Leslin says

    You’re right, the scarf does transform the outfit!!! But I also do like it with the green tee, its cute.. :) Come on, you do not look dumpy in any of those outfits! I have a couple of pretty maxi skirts that I purchased quite a while back but have never worn. Given the fact that I am not a very tall person, I just cannot figure out what to wear them with and worry how I would look in them. I have bought a couple of cute tops recently and finally pulled the skirts out of my wardrobe today.. Hopefully I will be brave enough to wear them at least now.. :)

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