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ClassyTrendy · June 27, 2024

25 Chic Pencil Skirt Outfits to Wear This Summer and Beyond

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Love pencil skirts? They are not only chic but also can be styled in numerous ways and worn to many different occasions. If you are wondering what to wear with a pencil skirt, here we have the 25 timeless outfits you will love and should try today!

Table of Contents

  • Tweed Blazer
  • Floral Off-the-shoulder Top
  • Matching Suit Blazer
  • Trench Coat
  • One-Shoulder top
  • Ankle Boots
  • White Sneakers
  • White Button-down Shirt
  • Short Sleeve Button Up
  • Corduroy Blazer
  • Navy V-Neck Blouse
  • Neutral Midi Coat
  • Denim Jacket
  • Leopard Prints
  • Moto Jacket
  • Crop Top
  • Knit Sweater
  • Quarter Sleeve Blouse
  • Satin Top
  • Basic White T-Shirt
  • Knee-high Boots
  • Skin Tone Pumps
  • Crop Cardigan
  • Flutter-Sleeve Blouse

Tweed Blazer

Graduation outfits for mom matching tweed skirt and blazer

Crush that boardroom game by rocking your pencil skirt with a sassy tweed blazer. The structured vibes of the blazer hug all the right places, shouting “boss” without saying a word.

Its texture is quite extraordinary as it’s like wearing confidence woven into every thread, adding a touch of mystery to your power play.

Floral Off-the-shoulder Top

Now’s the time to dial up the feminine vibes in your pencil skirt ensemble by teaming it with a floral off-the-shoulder top! Its neckline gracefully emphasizes your collarbones and shoulders, teasing with just the right amount of allure.

The floral print is not just a pattern but also a statement that introduces your attire with a burst of color and personality.

Matching Suit Blazer

how to look good in your 60s - tailored matching suit

Pairing your pencil skirt with a matching suit blazer is about confidently owning your style. The sleek lines of the blazer perfectly align with the clean silhouette of the skirt – it’s like they were destined to be together, harmonizing in both fabric and color for an effortlessly put-together look.

Trench Coat

Weather-proof your pencil skirt outfit with the ageless trench coat – your trusted shield against the elements, blending classic sophistication with modern flair! Its clean lines instantly level up your demeanor, exhibiting understated elegance that commands attention.

One-Shoulder top

By adding a luxurious one-shoulder top with over your pencil skirt, the well-structured silhouette of the top carries an air of elegance to your getup, turning heads wherever you go.

Ankle Boots

mini skirt with cold-shoulder top and ankle boots

Enhance your stride with a dash of daring by teaming your pencil skirt with ankle boots. Their simplistic yet impactful design glides effortlessly alongside the clean lines of your skirt, creating a fusion of chic sophistication and undeniable sass. 

The ankle-height shaft, nonetheless, acts as a leg-lengthening miracle worker, accentuating your femininity all day.

White Sneakers

Break free from conventions and flaunt your skirt with a pair of white sneakers – the unexpected pairing of sporty kicks with a tailored skirt creates a pleasing contrast. Their clean, minimalist design brings a touch of modernity and rebellion to your ensemble.

White Button-down Shirt

Graduation outfit pencil skirt and blouse

The combo of a white button-down shirt and pencil skirt – an effortless embodiment of sophistication, offering limitless stylish possibilities whether you tuck it in or leave it loose. The crisp lines of the shirt meld seamlessly with your well-fitted skirt, resulting in a simply polished look.

Short Sleeve Button Up

Have you tried infusing your pencil skirt ensemble with both modern chicness? Try a short-sleeve button up, the airy and oversized silhouette adds texture to your appearance.

The neckline adds a dash of finesse and provides fresh and airy feeling, making it a suitable pick for warmer weather.

Corduroy Blazer

turtle neck top with blazer and corduroy skirt

Envision yourself pairing your pencil skirt with a corduroy blazer – a style move that’s both classic and daring. The textured fabric of the blazer offers depth to your look, the lapel collar and button-front closure offer ageless elegance, and the corduroy fabric delivers a retro-inspired flair.

Navy V-Neck Blouse

16 best interview outfits for women

Ready to set sail into style? Try the nautical elegance of a navy v-neck blouse paired with your pencil skirt. 

The deep v-neckline establishes a silhouette that’s downright flattering and undeniably feminine as it displays your voluptuous busts. The relaxed fit of this ensemble is like a gentle breeze on a sunny day, wrapping you in chicness and ease.

Neutral Midi Coat

Chuch outfit button down and pencil skirt with wool coat

Experience the art of sophisticated simplicity with a neutral midi coat alongside your pencil skirt. The midi length of the coat cascades gracefully; the neutral color palette of the coat adapts to your every whim with ease, whether you’re keeping it classic or experimenting with bold accessories.

Denim Jacket

denim jacket outfits-pencil skirt

Why not unchain your style rebel with a denim jacket and a pencil skirt? This layering piece is a statement maker that blurs the lines between casual and dressed-up vibes, whereas the easygoing denim vibe gives off a hint of attitude and unexpected elegance.

Leopard Prints

leather jacket outfits- pencil skirt

Prepare to ignite your style with the untamed allure of leopard print adorning your pencil skirt. It’s a bold declaration of fierceness that sets you apart from the crowd – the contrasting colors of leopard print create a mesmerizing visual tapestry, adding an undeniable edge to your getup.

Moto Jacket

leather jacket- with midi skirt

Have you tried revving up your styling game with the urban chicness of a moto jacket and pencil skirt combo? The asymmetrical zipper and hardware give off a modern edge that’s sure to spark conversations, while the genuine or faux leather fabric of the moto jacket injects depth into your appearance.

Crop Top

denim jacket outfits-mini skirt

The cropped silhouette of a crop top adds a flirty charm and youthful vibe that’s impossible to resist, while its fitted design highlights your waist for a flattering silhouette. Wear it with a high-waisted pencil skirt to elongate those legs and accomplish a streamlined look.

Knit Sweater

suede boots outfit- with leather skirt

As you pair your pencil skirt with the luxuriously soft plush knit sweater, you’re enveloping yourself in warmth and the easygoing silhouette radiates understated elegance. The knit fabric and its intricate weave and subtle texture can definitely level up your outfit.

Quarter Sleeve Blouse

Magic happens once you pair your quarter sleeve top with your pencil skirt. Its fit boosts your outfit’s refinement due to its dimensional richness. The fitted profile of the pencil skirt, meanwhile, amplifies the contrast, creating a dynamic visual impact.

Satin Top

mini skirt and one-shoulder blouse

The satin texture and appearance allure and intrigue to your pencil skirt getup, drawing the eye upward and producing an eye-catching silhouette. When paired with a matching satin pencil skirt, you’ll achieve a streamlined and uniform appearance that’s head-turning.

Basic White T-Shirt

white shirt with leather skirt and midcalf boots

In terms of easy-breezy chicness, a few combos rival the pairing of a basic white t-shirt with a pencil skirt. The minimalism of the white tee serves as the perfect canvas to showcase the sleek and appealing profile of the pencil skirt.

Knee-high Boots

black knee-high boots With a pencil skirt

With knee-high boots, it’s not just about footwear – it’s a reliable sidekick that elevates your entire ensemble to a whole new level of refinement. The elongated silhouette of the boots gracefully complements the curve-hugging profile of the skirt, resulting in a well-polished look.

Skin Tone Pumps

Skin-tone pumps are more than just footwear – they effectively slim down your legs, particularly when paired with a perfectly fitted pencil skirt. The neutral color creates a seamless transition from your skirt to your shoes, visually extending your legs for an incredibly flattering silhouette.

Crop Cardigan

What To Wear With A Cardigan

What if I told you there’s a secret to adding a playful edge to your attire? Well, a crop cardigan pairs stylishly with a pencil skirt as the shorter length of the cardigan keeps the waistband of the skirt visible, highlighting your waist for a sexier frame.

Flutter-Sleeve Blouse

Visualize this: you’re stepping into the spotlight with unparalleled glamor – this is achievable with a flutter sleeve blouse paired with a pencil skirt! The stunning fit creates a striking contrast with the sleekness of the skirt, making this outfit a great pick for special occasions or whenever you want to make a memorable entrance.

Posted In: ClassyTrendy

Hello there! My name is Chi Li, 5'2", founder of PETITE DRESSING, the clothing line for women 5'4" & under. Are you petite and have you been frustrated with what to wear?
This is an issue few truly understand and even fewer brands truly address.
Being petite myself, I have been writing about fashion for short women since 2016 and my brand petitedressing.com has touched the lives of millions.
My styling concepts for petite women not only focus on the perfect fit but also on flattering & elongating the petite frame for a lean silhouette, optimizing the proportions.
Shop my clothing line here.

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