How to style a maxi skirt for winter

How to wear a maxi skirt

Nikki ParkinsonFashion, How to 29 Comments

I interrupt my planned programming today to bring you a follow-up post to yesterday’s winter maxi skirt outfit post.

SY reader Jo Morgan said on the Facebook page: “might need more styling pic options for encouragement. Always get stuck with tops/jackets to go with”.

And on Twitter, Julie Juratowitch asked, “Is there an age limit for wearing maxis? I love ’em but I’m turning 55 in a few months …”.

Well, Jo and Julie, I’m glad you spoke up because I went searching in the SY archives and while I’ve touched on the maxi a lot over the years, I’ve never published a post dedicated to their wardrobe usefulness. I’ve been remiss in dishing out specific advice about how to wear a maxi skirt.

… so no time like the present, I say.

The case for the maxi skirt

A maxi skirt looks effortlessly more stylish than a shorter option.

You feel that bit more dressed up, even though you may be in a casual outfit.

A maxi skirt means you can be a little lazy-girl in the hair shaving department.

And lastly, should you choose your maxi well, they can be the most flattering garment in your wardrobe.

Style tips

1. Starting with the right maxi skirt for your shape is the cornerstone to successfully pulling off this look.

The tube-style or slight A-line skirt is universally the most flattering (even you are shorter than average) style and is an easy base on which to add layers – summer, winter or trans-seasonal. Yes, there may be some lumps and bumps for the skirt to travel over (we are only human) but just like my case for the skinny jean, it really does come back to what you wear WITH the skirt to make this style work for you.

If you are pregnant this is definitely a go-to look. Keep the skirt and top streamlined and then add a cardi, jacket or kimono depending on the weather.

If you are tall and slender then by all means embrace a style that is gathered from the waist.

Another style that can work for most people, particularly if worn low on the waist, is this one as seen on Nina Proudman in Offspring. The band means that it sits flat on the tummy and then the gathering drops from below the band.

2. Adding layers to a maxi skirt should be done with a thought to proportions. The best outfit combinations balance out proportions and we’re dealing with a lot of fabric here so it’s even more important to play with what works for your shape.

So, if your choice is the waist-gathered, fuller maxi with lots of volume down below, then up top you need to keep things streamlined to the max so that your waist is emphasised. If belts are your thing, they work a treat with this look.

Conversely, with a streamlined maxi skirt you can afford to add a bit of volume up top with a slub tee, knit or shirt. And if you like a perfectly streamlined look, never fear it works as well. Belt lovers can add a belt to showcase their waist.

3. Don’t go too hard on the up-top volume. You are not aiming for a look that is tent like in proportions. The top layers can be loose but they need to skim the body and show your shape if the look is to work in a non-Little-House-On-The-Prairie** way.

4. Spring/Autumn look: team with a loose shirt, sandals, clogs, wedges or platforms. Avoid ballet flats with a maxi unless there is a little bit of ankle showing. If skirt is to the floor, then ballets can look out of proportion with the skirt, making you look shorter instead of elongated.

5. Summer look: keep things simple to keep your cool with a lightweight skirt, tank or tee and a necklace. Add a sheer kimomo top if cool. Sandals, clogs, wedges or platforms work here as well.

6. Winter look: team with layers. Start with a tank top, add a shirt, add a knit or a blazer and add a coat if needed. Underneath, wear tights. Ankle or knee-high boots with a small to medium heel work best to keep this look casual. Flat boots slip into the prairie territory mentioned above.

6. Choose a maxi skirt in a fabric weight you know you’ll be able to wear from Autumn through to Spring. This way you get more bang for your fashion buck and you just layer as required for the season.

7. This is not a style that should be limited by your age. Not that I think any style should be. The main thing is that you feel comfortable and confident wearing this look and team your maxi skirt with items that fit and flatter.

Maxi skirt: styled four ways

How to style a maxi skirt for summer

1. ASOS Curve maxi skirt  $21.02 (on sale) | 2. Harlow tee $48.97 (on sale) @ The Iconic | 3. Ruby Olive necklace $45 | 4. Windsor Smith platforms $149.95 @ Style Tread

How to style a maxi skirt trans-seasonally

1. Verily maxi skirt $65 (on sale) | 2.  Cat Hammill necklace $79.95 | 3. Country Road shirt $99.95 | 4. Funkis sandals $165

How to style a maxi skirt for winter

1. Metalicus maxi skirt $119.95 | 2. Witchery knit $99.95 | 3. Junk pea coat $109.95 @ The Iconic | 4. Trenery scarf $59.95 | 5. Mollini ankle boots $189.95 + whatever layers you need underneath to keep you warm

How to style a maxi dress for evening

1. Mossee maxi skirt $95 (on sale) @ The Iconic | 2. sass & bide capelet $550 | 3. The Mist earrings $39 (on sale) @ Molten Store | 4. Tony Bianco heels $149.95 | 5. Mimco clutch $249

For more maxi skirt styling inspiration, check out my dedicated board on Pinterest where I’ve pinned real women wearing maxi skirts – both the streamlined and gathered styles.

Hit me with your maxi skirt styling question and tell me which of these looks you can see yourself wearing?

** Once again showing my *maturity* with this reference. Younger readers, hit the Google search button now.

Comments 29

  1. Hey Nikki! I am really into the boots. Yet he brand name Timberland. Do you think I could wear them with a maxi skirt? Or would it be too masculine looking? Thanks so much 🙂

  2. Thank you for these helpful tips, I always find it hard to find tops to go with maxi skirts in Winter. I am not tall and feel a Maxi skirt makes me look shorter… you think it would? I tend to wear tights and jeans in Winter but I will venture out with a Maxi skirt now going by the wonderful ideas you posted! 🙂

  3. A dedicated post to my all-time-favourite wardrobe item!! Thanks Nikki 😀 I do the Nina-style maxi. I DO have to be careful as to which ones I wear as some of them can look terrible if they flare out on the wrong spot! I’ve always known how to tackle it in summer (tank, statement necklace, perhaps a lace vest) but this winter I’ve scoured your blog to work out how to incorporate it. So it’s normally teamed with boots, slimmer fitting top (winter equivalent to the tank!), and a cropped denim jacket or kimono.

    Thanks for your continued inspiration 🙂

  4. Maxi skirts can be flowing, tight fitting or shaped in various ways. I love wearing maxi skirts to cover my legs in spring/summer time! The maxi trend is one of my absolute favorite looks.

  5. Hi Nikki,
    As always, love your work and especially the way you are able to ‘speak’ to me (and many others) in an easy to understand, refreshing and engaging way. I have a few maxi skirts I had intended to wear during winter, styled as above, but got lazy and just threw my regular jeans or dress/tights/boots uniform on. You have got me back in the ‘change it up’ zone.
    Ps I don’t like to say but I know you’re a perfectionist so thought I’d mention there are a few missed words and typos in Point 1.

  6. Just don’t wear it with rubber thongs and a baggy football jersey like the woman I saw today at the petrol station, sans makeup or hair brushed. Pure class. NOT. Sorry that sounds mean – maybe she was just sick and couldn’t be stuffed?!

  7. We call these “Nina Skirts” – always look to Nina Proudman (Offspring) for styling! She wears them PERFECTLY. Little cropped jacket, accessories like long necklaces and scarves with boots! Perfect for winter.

  8. Fabulous! I love how you have shown the seasons! You are so clever!

    I am loving maxi skirts, I love the ‘illusion’ factor you can create… you can hide an awful lot under layers but still look trim…

    I LOVE the winter lookbook – I am so into navy and stone at the mo.


  9. Hmmm you’ve got me thinking now Nikki! Thanks for expanding on yesterday’s post. I might dig out my old black velvet A-line maxi and try my denim jacket with it for date night Friday. Off to check out the peacoat at the Iconic too…thanks as always for the inspiration xx

  10. I love this post! I have always loved the idea of maxi skirts but have been afraid to embrace them for fear of styling them badly. This post and your pinterest board just prove how versatile a maxi skirt can be. It is something I would like to add more of to my wardrobe as I think they would suit me.
    My favourite outfits are the second and third ones. I particularly like the idea of a printed maxi like the Verily one. Might just have to snap one up while they are on sale. I am still not convinced about me wearing a chambray shirt though. While I was not old enough to wear it the last time they were around I can remember my older sister having one. I can see that they have the potential to be fairly versatile but just not sure how it would look on me.

  11. I wear a maxi skirt in both Summer and Winter ,I live in maxi’s in summer and as long as the skirt or dress does not have too much fabric I am fine,I find they make me look taller,I am about 5ft4 but having a boyish figure they streamline me,no belts for me I look like a sausage tied in the middle or something.My favourite look is the winter and tran seasonal look and I know what you mean about flat ankle boots with a maxi dress or skirt very Little House on the Prairie ,that was one of My favourite shows I wanted to be Laura and live like that! Now I know better.I don’t think age comes into it at all either I think at I have got older I have embraced maxi lengths more as you can hide your shoes under,and can wear lower ones ,I also like a sheerer knit with a tank or a lonsleeve top under as it defines your shape more.
    Another thing I would like to add is no floral foofy skirts as they give off the aging hippy I came from Nimbin look:) You will be happy to know I picked up a shirt yesterday it is not as pale as I wanted and is more a denim colour but it is soft and for under $10 on the bargain rack in Target will do fine over leggings or skirts and it fits nicely,Thanks Nikki for this post.

  12. I have a grey and cream striped a-line maxi that is hanging in my wardrobe unworn since spring….I love the your outfit with the chambray shirt, but I know the CR one’s collar is too small for me and looks out of proportion. Do you have any other suggestions?
    Also, I note your outfits seem to favour a chunky shoe over a more streamlined sole. Is that right? I think this may be where I have gone wrong in the past, must do some trying on with what I already have at home to get this right.

  13. Thanks, you have given me some inspiration what to wear on the top. I like the pin board and the denim jacket looks good with the maxi . It looks easier to put together than I had envisaged. I’m off to shop for one!

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