Why We Love Pencil Skirt Outfits (And You Should, Too!)
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If your fall outfits need a refreshing new addition, you should buy a pencil skirt! With its form-flattering design and variety of lengths, pencil skirts channel the sassy vibes of our vintage bombshells and take any professional wardrobe up a notch. Read on for tips on how to style pencil skirts and check out photos of our favorite pencil skirt-centric fall outfits below.

Styling Your Pencil Skirts for Work

Transitioning your cute spring outfits into work-ready styles is simple with the versatile pencil skirt. Whether you’re a fan of the classic black pencil skirt or something a little more vibrant, pairing this staple piece with a smart blouse and the right accessories will instantly transform you into a professional fashion guru.

  • Start with neutral colors like beige, black, grey, and white to ease into the pencil skirt life/
  • Traditional patterns like houndstooth, plaid, and trendy chambray add a texture element to an otherwise sleek and stylish pencil skirt.
  • For a chic and subtle pop of color try deeper shades like maroon and navy. For a more vibrant spring outfit try royal blue, goldenrod or even pastel pink, mint green and canary yellow.
  • Never underestimate the power of a black pencil skirt, white button-down and blazer combo. Hello, power suit.

Making Your Pencil Skirt Outfit Less Vintage and More Modern

Despite the retro vibe every pencil skirt naturally gives its wearer, this classic design can easily be modernized with a few choice tops, shoes, and accessories. Pairing a casual, cotton pencil skirt with a crop top transforms it into a modern, comfortable look. Pair a nylon-blend, form-fitting pencil skirt with a matching white crop top and you’re a contemporary stunner, ready for a night out with Beyonce.

  • For an edgy look, pair a black pencil skirt with chunky ankle boots, a studded belt and a jean jacket. Punk it up.
  • Crop it like it’s hot. Pair your new skirt with crop tops and a colorful cardi or leather jacket to turn your style up a few decades.
  • Become one with your accessories! A cute brooch may scream 1950s, but a chunky necklace and some gladiator sandals are modern staples.

Creating Pencil Skirt Outfits for All Occasions

The benefit of having a pencil skirt in your closet is you’ll always have something to wear to any occasion. Whether you need a quick style for heading back to school, an eye-catching look for a celebration with friends, or something a little more romantic for a date night, the pencil skirt has you covered. Pencil skirts are an ideal item of clothing for any special occasion, pair them with floral patterns for spring outfits or pair them with lace and love (just not in white) for fall weddings.

  • Pencil skirts come in lots of lengths, show off your legs with an above-the-knee skirt and stilettos or rock it casual with a long skirt and stylish flats or sneakers.
  • Go glam with silver and gold accessories like chandelier earrings, sparkling statement necklaces and bangles for bracelets.
  • A sophisticated wedding calls for a classic style with a sleek silhouette. Turn in your wild patterns and frills for pearls, and if you’re a little more daring, red heels.
  • When in doubt, go minimalist with black-on-black or black and white and leave your accessories at home.

One of the best things about pencil skirts is they’re made for every body type and can easily be styled to fit your own brand. Whether your pencil skirt means big business in the boardroom or bar-hopping in NYC, this iconic piece is sure to liven up your spring wardrobe. From flirty spring outfits to cool winter get-togethers, pencil skirts are the versatile piece you need in your collection right now. What’s your favorite way to wear a pencil skirt?

The featured photo: When transitioning from winter weather to your spring wardrobe, hold onto those oversized sweaters a little longer and use Silvia Postolatiev as your guide. Pairing a tight-fitting pencil skirt (the lace is a bonus), classic pumps and a thick sweater provides style (and warmth) for those inbetween days.

Skirt: Guess by Marciano, Top: Unknown, Purse: DKNY, Watch: Daniel Wellington, Sunglasses: Victoria Beckham

Jessica Ricks wears a gorgeous pink suede pencil skirt with a cropped white tee and nude heels to create this spring-ready style.   Brands not specified.

Jessica Ricks wears a gorgeous pink suede pencil skirt with a cropped white tee and nude heels to create this spring-ready style.

Brands not specified.

Alex Rivière is wearing an elegant black pencil skirt with a cream sweater and heeled open toe boots to create this spring style. Throw on a pair of shades to get this look! Bag: Sandro Paris.

Alex Rivière is wearing an elegant black pencil skirt with a cream sweater and heeled open toe boots to create this spring style. Throw on a pair of shades to get this look!

Bag: Sandro Paris.

An effortless look from Kat Tanita shows us exactly how to pull off a classic, transitional day-to-night outfit in seconds. Pair a collared button-down and a knee-length pencil skirt with some comfy nude heels and you’re off! Skirt: DVF, Top: Rails LA, Shoes: Stuart Weitzman, Purse: Clare Vivier, Sunglasses: Celine, Necklace: Dogeared

An effortless look from Kat Tanita shows us exactly how to pull off a classic, transitional day-to-night outfit in seconds. Pair a collared button-down and a knee-length pencil skirt with some comfy nude heels and you’re off!

Skirt: DVF, Top: Rails LA, Shoes: Stuart Weitzman, Purse: Clare Vivier, Sunglasses: Celine, Necklace: Dogeared

A stylish pair of sneaks can definitely make a pencil skirt pop. Take a tip from Angelica Blick and combine an all white set (pencil skirt, crop top and sneaks) with coordinating jacket and purse for a cleverly casual and beautiful image. Skirt: Zara, Top: River Island, Jacket: ASOS, Purse: YSL, Shoes: Nike

A stylish pair of sneaks can definitely make a pencil skirt pop. Take a tip from Angelica Blick and combine an all white set (pencil skirt, crop top and sneaks) with coordinating jacket and purse for a cleverly casual and beautiful image.

Skirt: Zara, Top: River Island, Jacket: ASOS, Purse: YSL, Shoes: Nike

Jessica R. opts for a bold faux leather skirt paired with a girly pink top to create a fierce yet feminine style. Pair more punk (leather and jean) pencil skirts with florals, lace, or pastels to create eye-catching contrast. Skirt: Faux Leather, Top: West LA Boutique, Shoes: Steve Madden, Purse: Melie Bianco, Bracelet: Bebe, Earrings: Dainty and Bold

Jessica R. opts for a bold faux leather skirt paired with a girly pink top to create a fierce yet feminine style. Pair more punk (leather and jean) pencil skirts with florals, lace, or pastels to create eye-catching contrast.

Skirt: Faux Leather, Top: West LA Boutique, Shoes: Steve Madden, Purse: Melie Bianco, Bracelet: Bebe, Earrings: Dainty and Bold

Doesn’t Camille Charriere look ravishing in camel? Aptly named “camel-athon,” Camille proves that “coordination is everything” with her mix and match neutrals. Create a look that’s wild and tame with leopard prints and creamy shades of camel! Skirt: Filippa K, Top: Filippa K, Coat: Monki, Shoes: Jimmy Choo, Purse: Figaros Bryllup, Sunglasses: Celine

Doesn’t Camille Charriere look ravishing in camel? Aptly named “camel-athon,” Camille proves that “coordination is everything” with her mix and match neutrals. Create a look that’s wild and tame with leopard prints and creamy shades of camel!

Skirt: Filippa K, Top: Filippa K, Coat: Monki, Shoes: Jimmy Choo, Purse: Figaros Bryllup, Sunglasses: Celine

Amy Spencer is sporting one of our favorite modern, below-the-knee pencil skirts featuring pinstripes and a tie-waist. She pairs lighter neutrals (grey, white, and a chunky leopard print heel) together for a city-ready style, while showing off her tan with a cropped jumper. Skirt: Zara, Top: Topshop, Jacket: Topshop, Purse: Paul’s Boutique, Shoes: Missguided

Amy Spencer is sporting one of our favorite modern, below-the-knee pencil skirts featuring pinstripes and a tie-waist. She pairs lighter neutrals (grey, white, and a chunky leopard print heel) together for a city-ready style, while showing off her tan with a cropped jumper.

Skirt: Zara, Top: Topshop, Jacket: Topshop, Purse: Paul’s Boutique, Shoes: Missguided

Barbora Ondrackova is ready to run through the streets for her Starbucks in this all-black cropped top and pencil skirt combo. Switch out the sneaks for heels or booties and add a smoky eye and nude lip and you’ll be ready to run right through the night, too! Skirt: H&M, Top: Choies, Shoes: Adidas, Purse: Gucci, Sunglasses: Celine, Watch: Kapten&Son

Barbora Ondrackova is ready to run through the streets for her Starbucks in this all-black cropped top and pencil skirt combo. Switch out the sneaks for heels or booties and add a smoky eye and nude lip and you’ll be ready to run right through the night, too!

Skirt: H&M, Top: Choies, Shoes: Adidas, Purse: Gucci, Sunglasses: Celine, Watch: Kapten&Son

Mary Seng, too has the feminie rockstar routine down with a pretty pink pea coat, cableknit sweater and high-heeled booties. We love the combination of fabric and textures from the patent leather heels to the quilting on her purse. Don’t be afraid to mix and match metallic and soft materials to create your own signature look. Skirt: Helmut Lang, Top: Vince Camuto, Coat: Topshop, Shoes: French Connection, Purse: Chanel, Sunglasses: Nordstrom

Mary Seng, too has the feminie rockstar routine down with a pretty pink pea coat, cableknit sweater and high-heeled booties. We love the combination of fabric and textures from the patent leather heels to the quilting on her purse. Don’t be afraid to mix and match metallic and soft materials to create your own signature look.

Skirt: Helmut Lang, Top: Vince Camuto, Coat: Topshop, Shoes: French Connection, Purse: Chanel, Sunglasses: Nordstrom

Sazan Barzani is taking sexy to new heights with this tartan pencil skirt and high thigh slit! With a t-strap stiletto and an oversided (thin) sweater, you too can turn an otherwise relaxed look into a eyecatching outfit! Skirt: Shop Luna B., Top: Margaret O’Leary, Shoes: Sam Edelman, Purse: Treesje, Sunglasses: Celine, Bracelet: Gorjana

Sazan Barzani is taking sexy to new heights with this tartan pencil skirt and high thigh slit! With a t-strap stiletto and an oversided (thin) sweater, you too can turn an otherwise relaxed look into a eyecatching outfit!

Skirt: Shop Luna B., Top: Margaret O’Leary, Shoes: Sam Edelman, Purse: Treesje, Sunglasses: Celine, Bracelet: Gorjana

Louise Roe is going back to basics with black and white – even down to her white pedicure and we can’t get enough. With pencil skirts traditionally being made in black, this is one of the easiest outfits to style, but always remains current. Pair a black skirt and white top with colorful heels or statement jewelry to add even more zest to this anytime style. Skirt: Cmeo Collective, Top: Finders Keepers, Shoes: Monique Lhuillier, Purse: Jimmy Choo, Watch: Tory Burch

Louise Roe is going back to basics with black and white – even down to her white pedicure and we can’t get enough. With pencil skirts traditionally being made in black, this is one of the easiest outfits to style, but always remains current. Pair a black skirt and white top with colorful heels or statement jewelry to add even more zest to this anytime style.

Skirt: Cmeo Collective, Top: Finders Keepers, Shoes: Monique Lhuillier, Purse: Jimmy Choo, Watch: Tory Burch

Hit up your favorite rock concert in style like Lisa RVD in her pencil skirt and ACDC tee! Whether you’re working for the band or screaming in the crowd a rockstar supporter can’t go wrong with an all-black ensemble. Throw in a leather jacket and you’re ready to roll! Skirt: American Aparrel, Top: ACDC, Jacket: Zara, Shoes: Zara, Purse: Chanel, Sunglasses: ZeroUV

Hit up your favorite rock concert in style like Lisa RVD in her pencil skirt and ACDC tee! Whether you’re working for the band or screaming in the crowd a rockstar supporter can’t go wrong with an all-black ensemble. Throw in a leather jacket and you’re ready to roll!

Skirt: American Aparrel, Top: ACDC, Jacket: Zara, Shoes: Zara, Purse: Chanel, Sunglasses: ZeroUV

There’s something inherently gorgeous about blush and black that we had to share this ensemble by Linh Niller Huynh! The color combo is powerful yet feminine and a pair of Keds-style sneaks, a calf-length pencil skirt and a gorgeous coat can go a long way when you’re planning fresh spring outfits! Skirt: Sara Jane Knapp, Top: 360cashmere, Coat: J.Crew, Shoes: Stan Smiths

There’s something inherently gorgeous about blush and black that we had to share this ensemble by Linh Niller Huynh! The color combo is powerful yet feminine and a pair of Keds-style sneaks, a calf-length pencil skirt and a gorgeous coat can go a long way when you’re planning fresh spring outfits!

Skirt: Sara Jane Knapp, Top: 360cashmere, Coat: J.Crew, Shoes: Stan Smiths

Creating a new kind of downtown, big city pin-up Noor De Groot styles pinstripe pencil skirt with flowy white blouse and some strappy white heels. To keep your professional look more business casual, only tuck the front (or half of the front) of your button-down beneath your skirt waist. Roll those sleeves and grab your sunnies when spring starts easing towards summer! Skirt: Forever 21, Top: Zara, Shoes: Zara, Sunglasses: Karen Walker, Bracelet: Cooee, Necklace: Flor Amazona

Creating a new kind of downtown, big city pin-up Noor De Groot styles pinstripe pencil skirt with flowy white blouse and some strappy white heels. To keep your professional look more business casual, only tuck the front (or half of the front) of your button-down beneath your skirt waist. Roll those sleeves and grab your sunnies when spring starts easing towards summer!

Skirt: Forever 21, Top: Zara, Shoes: Zara, Sunglasses: Karen Walker, Bracelet: Cooee, Necklace: Flor Amazona