Cute Skirt Outfits | Timeless Styles

If you have been following us for a little while, you may be familiar with our first skirt outfits post. In it, we briefly described some popular types of skirts, and gave you some cute skirt outfits, both fully vintage and also in combinations with modern apparel.

As there are dozens of skirt types, we had to leave some of them out of that list, knowing that we would cover the rest in the future.

That time has come as we know expand our previous list, giving you a couple of more skirt outfits suggestions, and as always, focusing on vintage/retro designs without neglecting the potential that these have to combine with modern clothing.

Circle skirt

Being one of the most popular skirt types, the circle skirt kicks off our list.

As the name suggests, the circle skirt is characterized by a circular waist opening. It can be both a long and a short skirt, and it is very common for it to come pleated.

Note: You may have realized that a single skirt can be multiple types. For example, the circle skirt above is also a high-waisted, mini, and pleated skirt (see skirt outfits post for more details)

Due to their circular waist and their loose design, circular skirts are one of the best skirts when it comes to leg freedom and flow.

It is mostly casual attire and can be found across all eras, from the long 1950s skirts, up to the short and modern cheerleader skirts. The outfits presented now are evidence of this; on one hand, we have a full vintage outfit featuring a long circle skirt with a wide hem, and a modern one featuring a vintage bell-shaped circle skirt.

Circle skirt vintage outfit

As you can see, a full vintage outfit from the middle of the XX century can be arranged around a long circle skirt. A non-plain skirt like the one shown above, or a polka dot, is preferred as it adds to the traditional look.

For the feet, you can go for some cone heels, or if you don’t feel like wearing a higher heel, a pair of kitten heels are great. Loafers are acceptable if you want an even more casual look (women’s shoe types are shown here).

The top will have to be a standard 1950s blouse. A long-sleeved knit top or tailored blouse (plain coloured) are nice alternatives.

If you wish to add that final touch to your outfit you can go for a vintage hat. We got you covered with our guide on vintage hats and vintage headwear review.

Circle skirt vintage/modern outfit

Circle skirts are also very present in modern times and the following outfit is a great example.

Bell-shaped skirts widely popular circular long skirts, as their characteristic look allows for sexy and modern outfits. In combination with a crop top, you get exactly that. With endless different types of crop tops, you can go for a long sleeve (picture shown), an off-shoulder, or a pure rib crop top and all of them will look great.

For more information on tops, we refer you to our guide on tops.

As you can see, a prominent necklace also looks very good but it is not essential. Finally, for the feet, a pair of discrete heels like the pump or cone heels will do the trick.

Remember that modern outfits tend to be plained coloured and darker colours are preferred. You can try any colour combination that you like but be sure to match them well!

Wrapped skirt

The Wrapped skirt is very underrated as it is not as popular as other skirts, but it is definitely one of the most beloved.

A Skirt that wraps around at least one time (it could be more) in order for it to close is a wrapped skirt. These types of skirts usually come with a strap or tie at the waist to secure them, but you can also find some of them without one.

The skirt is casual, it can be long or mini, with hemline or without it, and comes in endless colours and designs. Comfort and their catchy look are their strongest points.

Wrapped skirt vintage outfit

As with other skirts, the vintage wrapped skirt extends below the knee and does not flare too much. Still, it allows for elegant and traditional feminine outfits.

Our outfit suggestions combine this type of skirt with different tops. You can have the puffy shoulders and long sleeve blouses with a collar or with the big bow on the front (image shown) but also buttoned down short sleeve shirts with collars look very good.

Depending on your style and formality, some discrete heels or slightly elevated shoes are the preferred choices.

Wrapped skirt vintage/modern outfit

To give a modern twist to your wrapped skirt you can go tops with more shoulder, belly, and breast exposure. The pure rib crop top (image below), one-shoulder crop, and tube top are some of these tops.

As a note, necklaces with matching formality and forms look very good with the tube top/wrapped skirt combination.

Looking at the shape and design of this skirt, you can see that high heels with some ankle exposure look both hot and innovative. Try going for T-strap heels or ankle straps.

Tiered skirt

The tiered skirt, also known as layered skirt, has a series of divisions so that the skirt is clearly layered. Most of the time, the layers are of the same material and colour, however, there are a few tiered skirts out there that don’t follow this.

You can find short, long, and even maxi tiered skirts, all of them being eye-catching and comfortable.

As for the layering design, different designers like to experiment with these, so you can find both very exotic and discrete designs. Patterns are also printed on them to make them stand out even more, but plain skirts are also common.

Tiered skirt vintage outfit

Our vintage outfit suggestion features a long printed tiered skirt which adjusts highly in your waist. A very common type of skirt in the first half of the past century.

For the shoes, you can go for a pair of pumps, or if you want to be more comfortable, a pair of flats. If you can match the pattern of the skirt, all the better.

The top has to contrast well with the skirt, so the plain colour is desired. As for the type, vintage blouses work well; a short sleeve with puff shoulders looks great (featured imaged) but so do b long sleeve and sleeveless blouses with a neck.

As you can tell from the picture, you can add a pair of gloves and headwear to the short sleeve blouse to make it look even better.

Tiered skirt vintage/modern outfit

A completely different outfit is achieved by just changing the top. Even a long tiered skirt with the characteristic vintage polka dots can be modernized with an adequate top.

Tube tops, off-shoulder tops, pure rib crop tops are all ideal alternatives for doing this.

Asymmetrical skirt

Asymmetrical skirts have quite an interesting design. By cutting the skirt on either or both sides of the skirt, different lengths are obtained, thus breaking the symmetry of the skirt.

One of the most popular asymmetrical skirt design is when the front is a little shorter than the back, however, there are countless different designs. Some break the symmetry on the sides, others on just one side, and others on the back. The difference in length also varies depending on the design.


You can find both short and long asymmetrical skirts, and you may even see them at formal events as these are considered elegant skirts.

Asymmetrical skirt vintage outfit

The vintage outfit suggestion involves an asymmetrical skirt with only a slight variation in length between the front and the back.

This one is more casual as you can go for a sleeveless blouse or even a tank top. As for the feet, some ankle straps, platform shoes, or sandals are comfortable and matching alternatives.

By the picture, you can tell that a matching headband look adds an innocent touch.

Asymmetrical skirt vintage/modern outfit

Contrasting to the vintage outfit, the modern one features a way more pronounced asymmetry and is much more daring and sexy.


You can see that ankle straps and similar shoes match very well with the asymmetrical skirt, as they look very nice when there is both a slight asymmetry and a very pronounced one. A higher heel is preferred one the modern one though.

On the upper body, we have an interesting combination of a tucked plain U-neck and a Denim jacket. A sleeveless alternative would look great once the jacket is off.

The big necklace, the sunglasses, and the watch are a plus.

Maxi Skirt

Our last featured skirt is the maxi skirt. As you can tell by the name, the maxi skirt extends to the maximum possible length, that is, to floor level. You can have any type of design, shape, or form, as long as it extends to the floor it is a maxi skirt.

Maxi skirt vintage outfit

Hippies loved maxi skirts, so a natural way to rock a vintage maxi skirt outfit is to adopt a full hippie look. The long leather boots in combination with the sleeveless top make up the outfit.


Hippies were also known for wearing lots of accessories. Wristbands, watches, rings, necklaces, as long as it matches the outfit’s casualty, you can wear as much as you want. Turbans and similar headwear are also welcomed.

One last thing: If you go for this look, remember that showering is not prohibited 😉

Maxi skirt vintage/modern outfit

Maxi skirts can also have a modern vibe to them. Cleaner designs with predominant darker colours will blend easier today. As the skirt usually covers the feet too, a pair of discrete low heeled shoes are preferred as they are comfortable and will look good for the brief time they can be seen.

For the top, go for modern designs of the one-off shoulder, the crop top, the off-shoulder, and others. Look for thinner tops with higher quality fabrics.

A brief reminder

So there you have it! We hope that this new list of skirt outfits helps you expand your wardrobe in ways that you’ve never imagined before. Remember to check out our skirt reviews to find about some of the best skirts available in online stores. You will not want to miss that!

Thank you for reading and don’t forget to comment down below your opinions, experiences, or feedback as your comments are very important for us.

Have a great day!

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2 thoughts on “Cute Skirt Outfits | Timeless Styles”

  1. It is interesting how fashion styles make the rounds and what is regarded as vintage, is making a come-back and is once again popular, even with the younger generation. 

    Do you think that certain body shapes are best suited for specific skirt designs? Which skirt do you think is the most flattering for a pear shaped body?

    1. Hey Line! That is a really good question. We are working on an article dedicated to the different body types and what types of clothing go well with each of them. Skirts will surely be covered there, so stick around for that 🙂

      Thank you for commenting!

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