Almost 100 Ways to Make Your Pencil Skirt Useful

It doesn’t matter if you are going to work, doing errands, going out for the evening, or just lounging on the weekend.  Age doesn’t matter, either.  There are so many ways to wear a pencil skirt that I am writing about it in two parts.  This is Part Two:  For the Cool Weather Seasons of Fall and Winter.  In the Spring, I wrote Part One:  For the Warm Weather Seasons of Spring and Summer (to see that post, click HERE.) In this updated post, there are now well over 100 ways to make your pencil skirt useful. 

Now that I see how versatile a pencil is, I have no idea how I ever thought I had to reserve it for business purposes only!

Some General Guidelines Regarding Pencil Skirts

First of all, age doesn’t matter, as you will see as you look through all these ways that you can wear a pencil.

Because of its slim shape, a pencil skirt is perfect for layering blouses, long vests, dusters, etc.  Create a column of color with a black tank or cami and a black pencil skirt (or any matching color top and pencil) and then add any kimono or duster.

A black pencil skirt is a classic that I recommend as a basic piece to have in your wardrobe.  In the outfit combinations below, if you do not have a black pencil skirt feel free to substitute with what you have.

A pencil skirt, dressy or casual, any length, can be worn with a fluid or oversized pullover during the fall and winter.  A top with a high-low hem or a split hem works well.  A swing top works, too.  Then you can add heels, tall tailored boots with a heel, heeled ankle boots, or loafers.   Heels (including kitten heels) usually look best with a pencil skirt, no matter what kind of footwear.  If it’s not too cold out, ballet flats are a casual runner-up.  With a casual pencil skirt, you could even wear sneakers, especially slip-ons or dressier ones such as metallics or wedges.

~All references to leather are recommended to be faux in order to be kind to animals.~

Fall/Winter Outfit Formula

Take a pencil skirt, any length + a fluid knit top, mock wrap top, turtleneck, layering tee, draped-front knit or tank top + a faux leather jacket  or leather cardigan.  Add dressy knee-high boots, tailored ankle boots or heels.  You may also want to add an angular bag and/or a scarf.

Outfit Ideas for Pencil Skirts:

Out for the Evening

1. Business/Evening:  A black velvet jacket + a satin blouse + black pencil skirt.  Or, use whatever color velvet jacket and pencil skirt you have in matching colors.  Or if your velvet jacket and pencil skirt are not matching colors, match the color of the blouse to the jacket or the skirt.
2. Evening or Dressed-up Day:  A black sequined tunic over a black pencil skirt.  Add black opaque stockings + black heels + black stud earrings.  If you have a black tunic without sequins, just add bling.
3. Evening or Dressed-up Day:  A black velvet blazer + a black shell + a black pencil skirt + black leggings.  Add black ankle boots + black bangles.  (All this black works because there are different textures.)
4. Evening or Dressed-up Day:  A kimono + a long pencil skirt in a matching color + a top that’s not too long.  Add a few pendants + some bracelets + boots.
5. Easy Evening:  A black lace tank top + a black pencil skirt + a black boyfriend cardigan.  Add nude heels.

   

6. Monochrome:  A brown lace top + a brown pencil. Add gold earrings & bracelets and brown or bronze pumps.
7. A black velvet blazer buttoned over a black pencil skirt.  Add black ankle boots + black bangles.
8. A brown lace top over a gray flannel pencil skirt.  Add black heels.
9. Pair a pencil skirt with an embellished cardigan. Add statement earrings.
10. A black sequined blouse + a black pencil skirt + a fur vest belted.

    

11. A black sequined blouse inside a short gray flannel pencil skirt.  Add a scarf (maybe even a faux fur scarf) as a belt + black ankle boots.
12. A white lace top + a black pencil skirt.  Add pretty black heels + a jeweled headband or hairpiece + black/gold/pearl/crystal bracelets.
13. A metallic tank tucked inside a pencil skirt + a bright-color cardigan.  Add a narrow gold belt + heels + a colorful necklace and bag.
14. Top a long cinnamon-color pencil skirt with a bronze silk tank.
15. A black lace tank top + a black pencil skirt + a v-neck cardigan.
16. A top that shows a little skin + a pencil skirt.

With a Tunic

1. A tunic tucked inside a gray pencil skirt + gray leggings.  Add a tan leather belt + boots that match the belt + gold hoop earrings + a necklace with charms.
2. A high-low hem tunic or a long white shirt over a pencil skirt.
3. A bright-color tunic over a black pencil skirt.  Add black heels + a long pendant (if you have one in black & green, that would be great!)
4. A black jersey tunic over a black pencil skirt.  Add black knee-high boots with a heel + nude stockings (for warmth; skip stockings if you don’t like to wear them.)
5. A black tunic belted in black over a black pencil skirt.  You might like to add gray or tan stockings.
6. Belt a long-sleeve black knit tunic over a brown maxi-length pencil skirt.
7. Wear a black embellished tunic over a short black pencil. Add small earrings & black ankle boots.

With a Graphic Tee

1. A graphic tee + a pencil skirt + ankle boots.  Add a pile of necklaces.
2. A graphic t-shirt messy-tucked in a short black pencil skirt.  Add textured tights + a choker + bracelets + heels or heeled sandals.
3. A graphic tee tucked inside a pencil skirt.  Add slip-on sneakers.  Tie a top around your waist.  If sunny, add sunglasses.
4. A black graphic t-shirt tucked inside a black pencil skirt + a blazer.  You might like to add a leopard-print belt.  Add heels + jewelry of choice.
5. A black faux leather jacket fastened over a graphic tee + a black pencil skirt.
6. Motorcycle jacket + a long-sleeve graphic t-shirt or any tee + black pencil skirt.  You might like to add black ankle boots or other type of boots.  If sunny, add sunglasses.
7. Casual Friday:  Tuck a graphic t-shirt inside a pencil skirt and top with a blazer. Add work-ready heels and perhaps a watch.

With a T-Shirt

1. A black t-shirt – whether sleeveless, short-sleeved or long-sleeved – is chic and sassy with a pencil skirt. Add earrings and/or a necklace.
2. A ruffled t-shirt + a pencil skirt.  Add tall boots + crystal stud earrings + a pearl bracelet.
3. Pair a silk t-shirt with a pencil skirt. You might like to add tall black boots.
4. A long-sleeve gray t-shirt over a gray flannel pencil skirt + a brown cardigan.
5. A gray tee + a maxi-length rust pencil skirt. Add a long gold pendant + a gold cuff and/or watch.
6. A long-sleeve t-shirt over a long pencil skirt + a bomber jacket.  Add hiking or moto boots.
7. A brown t-shirt + a black pencil skirt + a jean jacket.  Sling a brown belt over the tee.  Add a long gold pendant + a gold bar necklace + simple gold earrings + layer a cuff with a bracelet + a statement ring on the other hand + tall brown boots with a flat heel.

   

8. A t-shirt (sometimes layered with a blouse or a turtleneck) + a sweater/jacket + a pencil skirt.
9. A t-shirt tucked into a pencil skirt + a cardigan.  Layer necklaces.  Add a quirky pin or two + black stockings + black ankle boots.  For outdoors, add a moto jacket.
10. A gray t-shirt + a short black pencil skirt + a black faux leather jacket.  Add black tights + brown boots.
11. Any long-sleeve black t-shirt or top + a black pencil skirt.  Add ballet flats.
12. A long-sleeve t-shirt tucked inside a black pencil skirt.  Add flat ankle boots.
13. An oversize t-shirt + a long pencil skirt.  Add boots + a chunky scarf + a fedora hat.`
14. A white tee + a pencil skirt.

With a Jean Jacket

1. A jean jacket + a black pencil skirt + an ivory top.  Add black tights + a fur scarf as collar over jacket + black ankle boots.
2. A jean jacket + a black sequined top + a pencil skirt.  Add a delicate necklace in the neckline + a statement ring + heels.
3. A jean jacket + a navy blue pencil skirt + any top.
4. Top a short-sleeve tee & pencil skirt with a jean jacket. Layer a long & short gold necklace. Add a cuff layered with a chain bracelet + earrings + tall flat brown boots.
5. Jean jacket or faux leather jacket + a pencil skirt + a shell.  Add any boots, including biker boots, or footwear of choice.

With a Jacket or Blazer

1. A motorcycle jacket toughens up the ladylike pencil skirt. Wear this combination with any top of your choice.
2. A motorcycle jacket + a black pencil skirt + a camisole.  Add black heels.
3. Top a long-sleeve black t-shirt & rust maxi-length pencil skirt with a black moto jacket. Add cool necklaces + gold rings + heeled black boots.
4. A black faux leather jacket + a long-sleeve red top + a gray flannel pencil skirt.  Add tall black boots and tights.
5. Top a t-shirt & a pencil skirt with a faux leather jacket.  You might also like to add a belt.
6. Black leather jacket or black leather blazer + a black pencil skirt + a top of your choice.

   

7. A plaid blazer + a pencil skirt + a shell.  Add heels or tall boots.
8. A boyfriend blazer + a short black pencil skirt + a top of your choice.  Add tights + flat ankle boots.
9. A cropped black blazer + a black pencil skirt + a top that may show beneath the blazer.
10. A blazer + a pencil skirt + a printed blouse.
11. Simply top a t-shirt & pencil skirt with a blazer.

    

12. A blazer + a button-down shirt + a pencil skirt.  Add heels.
13. A blazer over a sweater over a t-shirt over a short pencil skirt.  Add ballet flats.
14. A brown jacket (tweed or not) + a gray flannel skirt + a long-sleeve gray t-shirt.

    

15. Partially tuck a gray t-shirt into a black pencil skirt and top with a bomber jacket.
16. A sweatshirt blazer open over a pretty printed t-shirt over a pencil skirt.  Add tall boots.
17. A safari jacket + a long pencil skirt in an earth color, such as rust + a t-shirt.
18. A sleeveless blazer + a black & white graphic t-shirt + a black pencil skirt.  Add tall black boots.

With a Turtleneck

1. Monochrome:  A turtleneck + a pencil skirt of the same color.  Add a statement necklace + nude heels. Or, wear a black turtleneck with a black pencil skirt and black boots.
2. A turtleneck sweater + a black pencil skirt.  Add a chain bracelet + some earrings + black tights + black heels.  Or, use any color pencil skirt and maybe boots in place of heels.
3. A black jacket open over a black turtleneck over a black pencil skirt.  Add tall black boots and nude stockings (for warmth, unless you don’t want to wear stockings…)
4. A chunky turtleneck sweater over a pencil skirt.
5. A black turtleneck + a black pencil skirt.  Add silver or gold jewelry + heels or ankle boots.

   

6. A thin black turtleneck tucked inside a black pencil skirt.  Add belt + boots.
7. A thin black turtleneck tucked inside a black pencil skirt + a black motorcycle jacket.  Add heels.  If sunny, add sunglasses.
8. A featherweight turtleneck over a pencil skirt.  Add heels.
9. A short-sleeve or long-sleeve black turtleneck over a black, charcoal or navy pencil skirt.  Add black tights + black ankle boots.
10. A blue or black turtleneck over a black pencil skirt.  Add black opaque stockings + gold bracelet and earrings.

With a Sweater

1. A crewneck sweater over a black pencil skirt.  Add a colorful scarf + black footwear.
2. A cream sweater with a lace hem over a black pencil skirt.  Add riding boots.  You might also like to add a blue, green or turquoise necklace + a couple of chain bracelets.
3. A mohair sweater over a pencil skirt.  You might want to add a black jacket or moto jacket.
4. An oversize sweater + a pencil skirt.  You might like to wrap a scarf infinity-style with the ends in front.
5. A cable-knit sweater over a pencil skirt.  Add opaque stockings + footwear of choice.

   

6. A big, cozy sweater + a pencil skirt, long or short.
7. A brown cashmere sweater over a long cinnamon-color pencil skirt.  Add a red-tinged belt over the sweater + a toned scarf at neck + tall brown boots + hoop earrings + a watch or bracelet + a snakeskin bag.  Feel free to use this as inspiration and substitute what you have.
8. A red cashmere sweater over a black pencil skirt.  Or use whatever colors you have.  Add black tights + heels + gold (earrings, bracelets, etc.)
9. Wear an ivory cashmere sweater over a black pencil. You might like to style this with a statement piece of jewelry, black pumps and your hair straight.
10. A short or long-sleeve cashmere sweater (or other knit) over a pencil skirt.  Add a chunky chain or black bracelet + heels.

    

11. Wear a blue or other color sweater over a black pencil skirt. Accessorize with a double strand of spaced beads, such as ivory and silver.
12. A long-sleeve black sweater over a black or gray pencil skirt.  Add black ankle boots.
13. A scoop-neck sweater over a black pencil skirt.  Add black opaques + black heels + a gold bracelet.
14. A wrap sweater or wrap cardigan + a pencil skirt.
15. Monochrome:  Match a sweater to a pencil skirt. Add heels. You might also like to add a blazer or bomber jacket.

With a Cardigan

1. A boyfriend cardigan + a pencil skirt + a t-shirt.  Add tights + flat ankle boots + jewelry of choice.
2. A black boyfriend cardigan + a short black pencil skirt + a white scoop-neck top.  Add a big bright scarf tied around neck + textured black stockings + tall black boots + a black beret or other hat.
3. Belt a boyfriend cardigan over a pencil skirt.
4. A duster cardigan, even with a hood + a long pencil skirt.
5. A gray, red or black cashmere cardigan buttoned in the middle (unbutton the top and bottom) worn as a top + a black pencil skirt.  Add a delicate gold necklace + black stockings, fishnets if you have them.

   

6. A structured cardigan and pencil skirt presents a ladylike image for business occasions. Combine with a blouse or toned sweater.
7. A red or other color drape-front cardigan + a black scoop-neck top over a black pencil skirt.  Add black tights + delicate gold necklaces.
8. A black drape-front cardigan + a black tank top over a gray pencil skirt.  You could add black flats + a double-strand of chunky gold chains + a narrow gold bangle.
9. Button a black cardigan, except for the top, over a pretty-color top that peeks out, over a black pencil skirt. Add black stockings & pumps & a black cuff.
10. A charcoal-gray cardigan + a blue-green t-shirt tucked inside a black pencil skirt.  Add tall black boots + crystal hoop earrings.

    

11. Gray cardigan + a long-sleeve gray top + a short black pencil skirt. Add black opaque stockings + a long gold pendant + earrings.
12. A brown cardigan with a faux fur collar or fur scarf + a brown or rust shell + a long rust-color pencil skirt.  Add nude heels, sandals or not.
13. Business:  Tuck a black lace tank inside a black pencil skirt and top with a colorful cardigan. Belt the skirt (try using color.) Add black sandals or pumps.

With a Shirt or Blouse

1. A plaid shirt tucked inside a pencil skirt.  Add a dramatic topper, such as faux fur.  You might like to add a sparkly necklace.  Add heels, ankle boots, loafers with a heel or tall boots.
2. A plaid shirt over a pencil skirt + a black faux leather jacket.  Add black ankle boots with a heel + a chunky chain bracelet + a few extra rings.
3. Tuck a white shirt inside a pencil skirt and top with a black leather blazer or alternative. Add black tights and pumps.
4. Tuck a silk shirt into a pencil skirt. Roll up the sleeves. Add chunky shoes or sandals and red lipstick.
5. Leave a blouse or shirt untucked over a pencil skirt. Add heels. You might also like to add a blazer or bomber jacket.
6. A printed shirt with black in it + a black pencil skirt. Add nude stockings + black heels (or black stockings + black cut-out booties) + a short gold locket in neckline.

   

7. Tuck a long-sleeve shirt inside a pencil skirt. Add sling-back pumps.
8. Start with a silk blouse & a pencil skirt. Then you might like to top with a blazer.
9. Give structure to a billowy blouse by tucking it inside a pencil skirt.
10. A black blouse with sequins + a gray, navy or black pencil skirt. If the blouse is a longer length with a nice drape, you can leave it out over the skirt.
11. Tuck a loose blouse into a high-waist pencil skirt. Reach for shoes with platforms or stacked heels.
12. Monochrome:  Black blouse + black pencil skirt.

More Ways to Wear a Pencil Skirt

1. Create a classy outfit by pairing a black cross-front top with a black pencil skirt. Then add bangles + hoop earrings + a watch.
2. A silk top (sleeveless, short-sleeve or long-sleeve) + a black pencil skirt.  Add black tights + black ankle boots.  You might also like to add a topper for extra warmth.
3. Tuck a printed silk top into a short black pencil skirt. Add nude or ivory heels.
4. An animal-print silk top tucked into a black pencil skirt + a toned turtleneck.  Add nude heels + faux leather gloves.
5. A leopard-print top + a short black pencil skirt + a jean jacket.  Add jewelry + black heels.

   

6. A sweatshirt in a color to match pencil skirt.  A solid black sweatshirt will look great with a black pencil.
7. A rain jacket + a cashmere v-neck sweater over a thin camisole + a black pencil skirt.  Add a belt + a necklace + a sports watch + a cap.
8. A hoodie + a tank top + a pencil skirt.  Add heels + a watch.
9. A peplum top + matching pencil skirt.  You might like to add boots.
10. A hip-length top over a pencil skirt. You might like to add a blazer, bomber jacket, ballet flats, slip-on sneakers or boots.

    

11. Any top or tee + a pencil skirt. Add heels. You might also like to add a blazer or bomber.
12. Tuck a shirt or t-shirt into a pencil skirt. Add heels. You might also like to wear a blazer or bomber jacket.
13. Wear a loose top over a long pencil skirt. Sling a belt over the top at a diagonal angle. Add heels or boots and jewelry of your choice.
14. Wear a topper of your choice over a column of color. For example, top a black sweater & a black pencil skirt with a brown suede jacket.
15. Slip a black lace top under a black cardigan or blazer worn over a short pencil skirt.

    

16. Pair a cold-shoulder top with a pencil skirt. Add a belt, hoop earrings and booties.
17. A long-sleeve top over a pencil skirt.  Add a coin belt slung low on hips.  Push back sleeves.  Add a wrist full of various colors and textures with narrow bangles on one wrist + a statement ring on the other hand.
18. Monochrome:  Pair a black jacket or cardigan with a black pencil skirt.
19. Classic/business:  Add a narrow belt over a sweater set & pencil skirt. Finish with kitten heels.
20. For business, pair a pencil skirt with a tailored jacket and/or a white shirt. You might then like to add a belt.

I share my outfit ideas and list them for you so that you can use them to put your clothes together every day without having to think about it.  This gives you lots more to wear out of what you have by just putting things together in different ways.

You can bookmark this post in your mobile phone to refer to whenever you want new ideas to help you create outfits with your pencil skirts.  I hope that it is helpful to you.  I’d really appreciate it if you would let me know by leaving a reply below this post!

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