Oh, I remember wearing pencil skirts. But the looks from 15 years ago are by no means comparable to the chic pencil skirt outfits I've spotted emerging with abundance during this summer-to-autumn transition. These options are elevating autumn skirt outfits like nothing else. When I first heard that pencil skirts were trending, I'll admit I was apprehensive; however, I should never doubt the fashion crowd's innate ability to refresh and update any look, no matter my memory of it.
Whilst A-line maxi skirts and more voluminous styles will certainly still appear as the season goes on, I appreciate the sleek, sharp cuts of a pencil skirt and how seamlessly they fit into an autumnal wardrobe. The beauty of these is how timeless they are. People seem to be reaching for materials and colours that have staying power, from denim knee-length pencil skirts to black maxi versions. There are also wool and leather pencil skirts in the mix, which feel like they were made for this time of year.
All this to say, the pencil skirt is back and it's holds a lot of promise for this season's outfits. Here are seven different ways you can style it as we welcome in autumn.
Pencil Skirt Outfit Ideas to Rotate This Season:
1. Sleeveless Top + Maxi Pencil Skirt
Style Notes: Autumn often comes in a rush, but I'm aware that oftentimes we experience quite a few weird weather days, alternating between boiling sun and sheets of rain. That's one reason why I appreciate Abisola's look. Pair a maxi pencil skirt with a sleeveless top, and you have an outfit with endless layering potential. Wear as is, or add a jumper or trench if it's too cold.
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The ruching gives this top the perfect amount of visual interest.
A black maxi skirt will pair well with nearly top or shoe.
These will work now and long into winter party season.
2. Jacket + Pencil Skirt + Boots
Style Notes: I love a taller boot with a long skirt. It's another unique way to incorporate layering and texture. Rebekah proves that a pencil skirt is one of the best silhouettes for skirt and knee-high boots outfits. Opt for a neutral, tonal palette for a look that'll remain a constant in your fall and winter wardrobe.
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Essential for wearing over everything, from T-shirts to jumpers.
The cut and shade of grey impressed me on this H&M skirt.
Crinkle leather, perfect heel height—these are absolutely on my autumn wish list.
3. Leather Pencil Skirt + Jacket + Heels
Style Notes: Wearing double denim is a go-to look of mine, but I think Ingrid's outfit is hinting at an even cooler rendition that's coming this autumn and winter: double leather. As several leather jacket trends take over this fall, I'm convinced styling a pencil skirt with yours in one of the chicest pairings, whether you opt for a bomber, zip-up or boxy silhouette.
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One of the most convincing faux leather jackets I've ever spotted. The button-up style is trending too.
Knowing that this is Khaite, I can guarantee it won't stay in stock for long.
I think sheer socks are such a fun way of switching up your usual shoe-and-sock pairings.
4. Pencil Skirt + Matching Jumper
Style Notes: The cosy season has entered the chat. That's why Sabina's look is such an ideal take for autumn dressing. A matching set that features a nice jumper and pencil skirt is bound to keep you both warm and stylish. It's the perfect swap for anyone who's sad to pack away their summer co-ords.
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The perfect pairing.
Cosy and chic all in one.
An eternally chic pair of shoes to have on hand.
5. Denim Pencil Skirt + Belt + Coat
Style Notes: Denim skirts have seen a resurgence in the last couple of years, and they're here to stay, shifting between various styles. I'm a huge fan of Slyvie's take. The knee-length denim pencil skirt is a classic, but she's modernised it with the help of a sleek brown coat and matching tights and a statement belt.
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A chocolate brown wool coat is a modern autumn staple that's replaced my usual black version. It's such a gorgeous tone!
The perfect length and shade of blue. This will be as versatile as your favourite pair of jeans.
A statement belt gives the just the right dose of texture to a classic outfit.
6. Windbreaker + Pencil Skirt
Style Notes: Pencil skirts usually lean dressy, whether you think about them in the context of officewear or dinner dates. However, I find them incredibly cool when they're styled in a more casual manner, as Viki has done so perfectly here. On mild autumn days that call for laid-back attire, pair yours with a windbreaker and a cool handbag.
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I love that this packs down into a small pocket-size parcel. So convenient for days out and autumn travels.
Linen is perfect for the nicer autumn days that often appear when we least expect them.
I haven't stopped thinking about this Alaïa bag since it dropped. The shape is so unique, and the colour options are made for fall outfits.
7. Leather Jacket + Black Pencil Skirt + Heels
Style Notes: For another classic pencil skirt outfit that you'll happily have on rotation, look to Anouk for inspiration. Her monochrome, all-black ensemble works for any occasion. You can dress it up with boots and heels for nicer moments, or swap those out for trainers when you want a cool outfit that's impeccably put together.
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I'd say this is the definition of a perfect leather bomber jacket. The funnel neck is too good.
A gorgeous skirt made of 100% cotton. It'll be breathable but easy to warm up with a long coat or tights.
Suede flats are a great autumnal replacement for strappy summer sandals or heels.
