When you think about dressing casually, you probably are more likely to consider jeans or pants. But skirts can be just as comfortable, casual and chic. Today let’s discover how to wear a skirt in a casual chic way.

How to wear a skirt in casual situations

Here in Singapore I don’t really have a favorite when it comes to the kind of bottoms I like to wear. I love dresses, pants and skirts almost equally. I wear skirts on dressy occasions but also to casual outings.

Here, you will find my tips on how to wear a skirt in a casual way.

How to make your skirt more casual

  • Pair your skirt with with lose and casual tops
  • Wear brogues or sneakers with your skirt
  • Wear a skirt in a casual fabric like denim
  • Pair your skirt with casual fabrics like denim

Casual skirt looks for you to try

I think you can make pretty much wear any skirt work in a casual way.

You could, for example even pair a formal, full skirt with a denim jacket and a pair of sneakers.

But, obviously, some skirts are naturally more casual than others.

Denim skirts

Denim or jean skirts are a style staple that are unlikely to date, no matter how long they are in their closet.

You could opt for a classic blue or black denim, or if you want to wear during the summer months, you could try a white denim skirt instead of a pair of white jeans.

denim skirt | 40plusstyle.com

Frame vintage button front denim skirt

full denim skirt | 40plusstyle.com

Sandra (above) wears a lovely full denim skirt which she styles with pops of red. You can find a similar piece here.

bow denim skirt | 40plusstyle.com

Adaline got her her tie-belt skirt from Gap. You can find a similar piece from the same brand here.

Pleated skirts

Pleated skirts were once thought to be strictly formal.

They’ve been used by schools as part of school uniform, they were a style staple in the 40s and they look lovely dressed up now for a special occasion.

But, they also look very stylish when worn casually. I love the current trend for wearing a pleated skirt with a sweater and either sneakers or booties.

pleated skirt | 40plusstyle.com

Vince pleated mixed media skirt

white pleated skirt | 40plusstyle.com

Karen (above) teams her pleated skirt with a camisole and flat sandals for a great vacation look. Get a similar white pleated skirt here.

multicoloured pleated skirt | 40plusstyle.com

Erin (above) opts for colorful pleats worn with sandals and a sleeveless jacket. Check out a similar colored pleated skirt here.

Maxi skirts

I always think maxi skirts give off an air of casual elegance.

When you see a woman in a maxi skirt, she exudes haven’t-tried-to-hard confidence. You can wear with sandals for your vacation.

Or you could team with booties and a moto jacket when the weather cools down.

maxi skirt | 40plusstyle.com

Loveappella roll top maxi skirt

leopard print maxi skirt | 40plusstyle.com

Christine (above) wears her animal print skirt with booties and a denim jacket. Check out a similar piece here.

pink maxi skirt | 40plusstyle.com

Patricia (above) lets her maxi skirt be the stand out star of her outfit (along with a lovely, matching bouquet of flowers). Get a similar satin skirt here.

Pencil skirts

Just like the pleated skirt, the pencil skirt can be thought of as a more formal style.

And, it’s true, you can definitely dress it up for dinner, or you can wear with a blouse or shirt for work.

But, you can also dress the pencil skirt down with flats, boots or sneakers.

pencil skirt | 40plusstyle.com

J Crew leopard pencil skirt

snake skin pencil skirt | 40plusstyle.com

Nicky (above) wears her snake print pencil skirt with booties and a sweater. Here is a similar snake print pencil skirt.

how to wear a skirt in a casual way - floral pencil skirt | 40plusstyle.com

Grace (above) chooses a floral skirt and a blouse with dramatic, flared sleeves. You can find a similar floral pencil skirt here.

Full skirts

Another versatile option, full skirts can be a good option for many different body shapes.

But, they are particularly good for pear shapes as they help to skim over the thigh and hip area.

Check out this piece for more ideas on how to dress the pear shape.

full skirt | 40plusstyle.com

Tibi liquid drape skirt

printed full skirt | 40plusstyle.com

Sabina (above) wears a striking print skirt and choosing to add extra drama with a pair of gold sandals. Check out a similar navy printed skirt here.

red full skirt | 40plusstyle.com

Galiya (above) shows how effective layering can be. She teams her outfit with a blue sweater and also picks up the blue with her tights. Get a similar red skirt here.

I love to wear my wrap skirt from Cos (here is a similar one) that can combined with almost any top and looks great with my Rollie brogues.

For more inspiration, check out our article on black skirt outfit ideas.

Tops and jackets to wear with your casual skirts

If you are putting together a casual skirt outfit, you will want to make sure that the other elements of your look are not too formal.

Think about choosing sweaters, draped tops and casual jackets such as a leather biker or denim style.

Tops to wear with your casual skirts | 40plusstyle.com

Shoes to wear with your casual skirts

To ensure that your look sticks to a casual vibe, opt for booties or sneakers.

If you’re dressing for summer or a vacation, you could also choose sandals.

Shoes to wear with your casual skirts | 40plusstyle.com

Accessories to wear with your casual skirts

Keep your look suitable for daytime by opting for more casual options such as a crossbody bag and a scarf.

Rather than more formal jewelry such as diamonds or precious gems, you could think about more contemporary pieces.

Accessories to wear with your casual skirts | 40plusstyle.com

Here are 9 casual skirt outfits featuring the pieces above

Capsule wardrobe on how to wear a skirt in a casual chic way | 40plusstyle.com

Read our ultimate guide to creating a capsule wardrobe that works best for you.

Do you wear a skirt in a casual setting? Which of the above looks is your favorite?


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How to wear a skirt in a casual chic way | 40plusstyle.com

Feature image by Nicky


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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