What To Wear With A Skirt: Inspiration For Every Style - THE STYLE INSIDER

Whether you’re dressing up for a night out or heading to work, skirts are a great option for the majority of occasions. They ooze sleek feminine vibes and show off your figure beautifully, cinching you in at the waist for a slimming effect on the tummy. Versatile and universally flattering, it’s no wonder why skirts are a go-to piece for most women. We all have a trusty skirt in our wardrobe, but why not experiment by wearing a totally different style? Don’t worry if you’re not sure what to wear with a skirt that’s out of your comfort zone, Rob’s here to help. With everything from glam midis to sassy leather, our style guide will help you strut your stuff in any type of skirt.


When it comes to what to wear with a skirt, simplicity is key. Knotted shirts in neutral colours are perfect for a casual look, especially when paired with low-top trainers and a leather backpack. Blouses, wrap coats and heels make most skirts appear more formal, but avoid denim and stick with midi lengths.



We love leather skirts on practically anyone, making them a staple piece in any women’s wardrobe. Perfect with heels and a stylish crop top on a night out, it’s easy to incorporate a leather skirt into your current go-to outfits.

When it comes to everyday looks, let the leather take centre stage by pairing it up with a plain black or white sweater depending on your choice of skirt. Black leather is a classic, but opting for a bright colour will make your outfit really pop. Add a matching scarf to create interesting visual layers while keeping the cold at bay.

You can still rock a leather skirt during the warmer seasons, just swap the sweater for a cute lace cami. It brings a touch more femininity to a naturally edgy piece for the perfect balance of traditionally cute and trendy.

If you’re going after that popular grunge-inspired look, choose a pair of biker boots, otherwise opt for traditional Chelsea boots. Swap these out for a pair of black heels to turn the look from day to night.

Rob’s Top Tip: Fitted leather skirts look great with a baggier top, especially when it’s loosely tucked into the waistband. This look will show off your legs and hips without unflatteringly clinging to your body.



Pencil skirts are the epitome of sophistication, so much so that people often mistake them as solely just for work. While yes, pencil skirts do look amazing around the office, this is far from the truth. They make stunning outfits for more dressy events too, hugging your body to create a slim silhouette without breaking the dress code.

Pair a pencil skirt with a sleek sleeveless blouse for a classic outfit that can be worn from the office straight to an upmarket bar. Add some sparkle with metallic high heels and opt for a classy wrap coat if it’s cold outside to cinch in your waist.

If you’re after something more casual, choose a knee length black pencil skirt and tuck in a striped long sleeved tee. Go for one with an on-trend high neck to turn this classic dressy skirt into a fashionable everyday look. Not keen on this style? Trade it for a classy midi skirt of your choice and continue following these style tips.  

Rob’s Top Tip: Although you’ll be almost fully covered with the long sleeved option, don’t worry about losing your figure. The slim fittings pieces mould to your body to create curves and flaunt your shape.



Surprisingly versatile for everyday wear, pleated skirts are very much on-trend at the moment. When it comes to what to wear with a skirt like this, the key is to not overthink it. Anything that you wear with jeans typically looks great with a longline pleated skirt so there’s no need to update your wardrobe.

Pleated skirts look amazing with a simple white tee and trainers, especially when the skirt is a vibrant colour – we love reds and greens in winter but switch them out for yellow and orange in summer. White really makes colour pop and is guaranteed to turn heads for all the right reasons.

A leather jacket is the perfect option to go with a pleated skirt, bringing a contemporary edge to a classically feminine outfit. If you’re planning on rocking the pleated skirt during winter, a faux fur lined jacket will keep you snug and stylish.

Pleated skirts are extremely versatile and easy to style for the office. Opt for a classy black or silver shimmer skirt and tuck in your favourite plain slim fit shirt. Swapping your old skirts for one with a gorgeous pleat detail transforms typical office wear into a stylish outfit that your colleagues are sure to envy.

If you’re not keen on this type of skirt, swap it for a midi wrap version and style it the same.

Rob’s Top Tip: Head straight to the bar from work but undoing a few buttons and knotting your shirt at the front to create a crop top. Roll up the sleeves messily, add some a statement necklace and you’ll be good to go.



Undoubtedly a favourite for most girls, nobody should be without a denim skirt. They have to be one of the ultimate pieces when it comes to casualwear simply because they suit practically anyone and anything. Crop tops? Check. Lace camis? Check. Jumpers? Yep, those too. Whatever your personal style may be, you need a denim skirt or two.

As mentioned, denim skirts are probably the easiest to style in terms of everyday outfits. Don’t overthink the look, opt for a simple white long sleeve and contrasting black trainers. A trendy bomber jacket is perfect breezy evenings and can be wrapped around the waist when not in use. This will pull you in at the waist while exuding preppy chic. Finish it off with a belt for a stylish outfit that’s quick to pull together in a moment’s notice.

Feeling chilly? Luckily for you, denim skirts look great with tights and knitted jumpers. Known as a French tuck, create contrasting hemlines by tucking the front of a jumper into the skirt while leaving the back loose. Neutral colours such as cream, grey and muted browns complement denim skirts beautifully, making them a great choice for knits.

Fluffy parkas are a reoccurring winter trend year after year, making them the ultimate coat for your winter wardrobe. We love how they look over slimline denim skirts in the winter, especially when worn with sophisticated ankle boots.

Rob’s Top Tip: Belts are often overlooked as an accessory, but a chunky belt buckle can actually make an outfit. As well as being practical, belts pull in material to ensure you aren’t swamped while adding another eye-catching element to the outfit.



Animal print is a ‘loud and proud’ pattern, let the skirt do the talking by choosing a casual knitted roll neck top that complements the main piece without stealing the thunder. Sticking with one pattern ensures the outfit remains classy rather than overly brash or clashing.

Black, red and metallic rust tones complement most types of animal print, more specifically leopard. The make the outfit pop, highlighting the skirt rather than distracting from it. Incorporate these colours into your outfit to really turn some heads – we recommend a red or rust coat to throw on over the top when it gets chilly.

Feeling the heat? Trade your trusty roll neck for a scallop trim cami to add some feminine detailing and wrap a light sweatshirt around your waist to prepare for the colder afternoons. If you’re heading to the bar, simply ditch the jumper and replace it with a sleek black kimono.

Rob’s Top Tip: Less is more when it comes to leopard print and other animal patterns. If you do fancy pairing it with another print, do so with a small element of your outfit such as your purse or accessories.



Beautifully beachy, maxi skirts keep you cool but covered. Despite often being mistaken as being for tall girls only, maxi skirts are essential during hot summers regardless of your height. Women on the short side should look in the petite section when looking for a maxi skirt or go for one a few inches shorter than the typical maxi.

Styling a maxi skirt for the summer is a lot easier than you’d think. Cold shoulder tops are playful and fun, highlighting your clavicle to achieve a slimming effect. Tuck it into the skirt with a thin waist belt before finishing off the outfit with some stylish gladiator style sandals.

If you’re dreading putting away your maxi skirts for another year when Summer ends, don’t worry, they work surprisingly well during Autumn. Pair a slinky on-trend roll neck and heels with a floral maxi skirt for a sleek feminine look that’s perfect for both the office and a catch up over coffee with some friends.

Rob’s Top Tip: If you’re worried about maxi skirts shrinking your height, get one with a slight slit up the leg. This will show a glimpse of your body, showing off your height rather than hiding it.