As far as wardrobe staples go, the pencil skirt will always rank high for me. It’s that trusty friend that makes you look put-together with almost zero effort.
But are you ready to take it beyond the boardroom? I’ve rounded up 21 of the absolute best pencil skirt outfits that are perfect for a girls’ night out, a casual weekend, and everything in between.
Trust me, you’re going to want to screenshot these.
1. Cozy Chic
I am obsessed with an outfit that feels both cozy and chic. For this look, I’d pair a long-sleeved cream-colored sweater with a slim black pencil skirt. It’s such a simple outfit formula, but the outcome is always so cute.
You can slip on some comfortable black pointed-toe flats and finish the look with a black handbag. This is the perfect combination for a laid-back day at the office or for meeting up with your girlfriends for lunch.
2. Boss Babe Vibes
Here’s an outfit that will have you feeling like the boss you are. I love styling a high-waisted black pencil skirt with an aqua scoop neck tank top.
To add a polished touch, throw on a cropped black blazer with 3/4 length sleeves.
The real showstopper here is the pop of color from the teal suede pointed-toe heels. I personally think this is the ideal look for a day at the office when you want to feel professional but still let your style shine.
3. Denim Darling
For a look that’s both casual and totally chic, try pairing a denim pencil skirt with a loose-fitting off-white cardigan. This combo is just so effortlessly cool.
Slip on some pointed white ankle boots and grab a small white handbag to pull the whole thing together. This is my go-to formula for running errands or grabbing lunch with friends on the weekend.
4. Disco Ball Chic
Ready for a girls’ night out? You can’t go wrong with this look. I’m talking about a silver sequined miniskirt paired with an olive green cold-shoulder top that has the cutest ruffled sleeves.
For a little extra drama, add some sheer black tights and black ankle boots with a slight heel. This outfit is an absolute must for a bachelorette party or any night when you want to be the center of attention.
5. Fifty Shades of Gray
I am a big believer in the power of a monochrome outfit. You can lean into it by pairing a gray sweater with a matching grey pencil skirt.
To complete the look, I’d slip on some black patent leather loafers and grab a small black handbag.
This combo is a perfect choice for a day at the office or a business meeting where you want to look both stylish and professional.
6. Wild Thing
If you want to add a little something extra to your pencil skirt look, this is for you. A white denim pencil skirt looks amazing with a loose-fitting leopard print blouse.
To keep the vibe casual, finish the outfit with some black and white high-top sneakers. This one is ideal for running errands or grabbing coffee with friends on the weekend.
7. Winter Whites
For a seriously chic monochromatic moment, you have to try this. Pair a long-sleeved, oversized white sweater with a white pencil skirt. To make your legs look a mile long, add some nude pointed-toe heels.
I love how a camel shawl and a structured handbag in the same color pull it all together. This outfit is a dream for a winter wedding or any fancy holiday event where you want to look super elegant.
8. The Ultimate Girls’ Night Out Look
If you want a look that says you’re ready to have some fun, look no further. Start with a fitted black sleeveless top that has some pretty lace detailing and pair it with a shiny black patent leather mini pencil skirt.
I’d add some edgy black ankle boots with pointed toes and accessorize with black cat-eye sunglasses and a structured black handbag. This is just perfect for hitting a trendy bar or dancing all night with your besties.
9. Pattern Play
Why not mix things up a bit? I love a fitted knee-length blue pencil skirt styled with a black and white patterned long-sleeve sheer top.
To give it some edge, you can add sheer black tights and black ankle boots. This outfit is such a great choice for a night out with the girls or even a creative business meeting where you want to show off your unique style.
10. Retro Romance
Let’s take a little trip back in time! How cute is a knee-length pencil skirt with a playful cherry print? Pair it with a long-sleeved black top for some contrast.
To really lean into the vintage vibe, add a pair of classic black T-strap heels. This would be so fun for a retro-themed party or a quirky date night with your person.
11. Blushing Beauty
For a look that is so romantic and feminine, try a white tube top with a lace pencil skirt in soft pink. I love this combo.
You can slip on some clear heeled sandals so the skirt can really be the star of the show.
This outfit is a total dream for a spring or summer wedding, a bridal shower, or a date night where you want to feel sweet and flirty.
12. Stripes and Sandals
This is such a fun, summer-ready look. Pair a black knee-length pencil skirt with a short-sleeved blouse featuring black and white vertical stripes.
The best part is the pop of color from the green and white sandals. Trust me, this outfit is a great choice for a casual day at the office or a lunch date with your besties.
13. Ruched and Ready
Here’s how to create a really sophisticated look. I’d start with a taupe-colored blouse that has ruching details and style it with a fitted, high-waisted black pencil skirt.
To give it a touch of retro glam, just add some round sunglasses. This is the kind of outfit that’s perfect for a fancy lunch or a day at the races when you want to look super polished.
14. Edgy and Effortless
I am such a fan of this effortlessly cool look. All you need is a black leather skirt paired with a fitted white crop top and a denim jacket.
To finish it off, I would add black knee-high boots for a bit of extra edge.
This combination is a definite must-have for a concert or a casual date night when you want to look put-together without trying too hard.
15. Lady in Red
If you’re looking to make a statement, this is the outfit for you. I just love a bright red fitted pencil skirt, especially when it’s paired with a black button-down shirt.
To add a little drama, you can wear black sheer tights and black heels. This is my top pick for a fancy date night or a girls’ night out when you want to feel totally confident and sexy.
16. Pretty in Pink
You can really embrace your feminine side with this look. I would style a bright fuchsia pink pencil skirt with a fitted white tank top that has a sweetheart neckline.
To add a little extra something, layer a lightweight floral bomber jacket on top. The finishing touch? A pair of fuchsia pointed-toe pumps.
This outfit is perfect for a spring or summer event, like a bridal shower or a fancy brunch with the girls.
17. Off-Duty Cool
For a vibe that’s both laid-back and stylish, you can’t go wrong with this combination. An oversized, cozy gray sweater looks so good with a fitted black pencil skirt.
To keep it casual, just slip on some gray ankle boots. This is my ideal outfit for running errands on the weekend or grabbing a coffee with a friend.
18. Boho Babe
Let your inner free spirit shine with this one. I am so into a tie-dye t-shirt in shades of blue and pink, especially when it’s paired with a sequined silver skirt featuring a playful scalloped hem.
For a cohesive look, I’d accessorize with a small pink handbag and matching pink strappy sandals.
This outfit just screams music festival or a laid-back summer party where you want to look cute and carefree.
19. Teal Tease
I love a bold statement, and this outfit delivers. Start with a teal blue pencil skirt and pair it with a black and white checkered blouse. Then, slip on some classic black pointed-toe pumps.
To complete the look, I’d add a black beret and a black handbag. This whole vibe is perfect for a fancy brunch or a day at the races where you definitely want to stand out.
20. Back in Black
You can create such a sleek, all-black outfit with this formula. A fitted black sweater with long sleeves paired with a black midi-length pencil skirt is just so classic.
To make your legs look longer, slip on some black pointed-toe pumps. This look is a guaranteed win for a fancy dinner or a night at the theater when you want to look chic and sophisticated.
21. Subtle Sparkle
For a more low-key take on sequins, try this. I’d pair a sequined midi skirt in muted silver with a cozy, cream-colored oversized sweater.
To keep your legs warm and toasty, you can slip on some beige suede knee-high boots.
This outfit is a perfect choice for a holiday party or a winter date night when you want just a little bit of sparkle without going over the top.
And there you have it! 21 chic and stylish pencil skirt outfits for whatever you have planned.
Whether you’re headed to the office, a special dinner, or a casual brunch, these looks will have you feeling your absolute best.
