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.)

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.  I encourage you to save the ideas you like out of my posts and put them in a place to easily refer to as needed.  I hope that it is helpful to you.  Let me know by leaving a reply below this post!

Some General Guidelines Regarding Pencil Skirts

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 metallic 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, drapey 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. A brown lace top over a gray flannel pencil skirt.  Add black heels.
7. A motorcycle jacket + a black pencil skirt + a camisole.  Add black heels.
8. A black velvet blazer buttoned over a black pencil skirt.  Add black ankle boots + black bangles.
9. A black sequined blouse + a black pencil skirt + a fur vest belted.
10. 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.
11. A white lace top + a black pencil skirt.  Add pretty black heels + a jeweled headband or hairpiece + black/gold/pearl/crystal bracelets.
12. A metallic tank tucked inside a pencil skirt + a bright-color cardigan.  Add a narrow gold belt + heels + a colorful necklace and bag.
13. A black lace tank top + a black pencil skirt + a v-neck cardigan.
14. 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.

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.

With a T-Shirt

1. A ruffled t-shirt + a pencil skirt.  Add tall boots + crystal stud earrings + a pearl bracelet.
2. A long-sleeve gray t-shirt over a gray flannel pencil skirt + a brown cardigan.
3. A long-sleeve t-shirt over a long pencil skirt + a bomber jacket.  Add hiking or moto boots.
4. 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.
5. A t-shirt + a pencil skirt + a faux leather jacket.  You may also like to add a belt.

   

6. A t-shirt (sometimes layered with a blouse or a turtleneck) + a sweater/jacket + a pencil skirt.
7. 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.
8. A gray t-shirt + a short black pencil skirt + a black faux leather jacket.  Add black tights + brown boots.
9. Any long-sleeve black t-shirt or top + a black pencil skirt.  Add ballet flats.
10. A long-sleeve t-shirt tucked inside a black pencil skirt.  Add flat ankle boots.
11. An oversize t-shirt + a long pencil skirt.  Add boots + a chunky scarf + a fedora hat.`
12. 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.  Jean jacket or faux leather jacket + a pencil skirt + a shell.  Add any boots, including biker boots, or footwear of choice.

With a Jacket

1. A black faux leather jacket + a long-sleeve red top + a gray flannel pencil skirt.  Add tall black boots and tights.
2. A blazer + a pencil skirt + a printed blouse.
3. A blazer + a button-down shirt + a pencil skirt.  Add heels.
4. A blazer over a sweater over a t-shirt over a short pencil skirt.  Add ballet flats.
5. A brown jacket (tweed or not) + a gray flannel skirt + a long-sleeve gray t-shirt.

   

6. A plaid blazer + a pencil skirt + a shell.  Add heels or tall boots.
7. A boyfriend blazer + a short black pencil skirt + a top of your choice.  Add tights + flat ankle boots.
8. A cropped black blazer + a black pencil skirt + a top that may show beneath the blazer.
9. A sweatshirt blazer open over a pretty printed t-shirt over a pencil skirt.  Add tall boots.
10. A safari jacket + a long pencil skirt in an earth color, such as rust + a t-shirt.
11. A sleeveless blazer + a black & white graphic t-shirt + a black pencil skirt.  Add tall black boots.

With a Turtleneck

1. A turtleneck + a pencil skirt of the same color.  Add a statement necklace + nude heels.
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 white 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 black 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 red cable-knit sweater over a black pencil skirt.  Add black 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. A short or long-sleeve cashmere sweater (or other knit) over black pencil skirt.  Add a chunky chain or black bracelet + black heels.
10. A long-sleeve black sweater over a black or gray pencil skirt.  Add black ankle boots.
11. A scoop-neck sweater over a black pencil skirt.  Add black opaques + black heels + a gold bracelet.
12. A wrap sweater or wrap cardigan + a pencil skirt.

With a Cardigan

1. A duster cardigan, even with a hood + a long pencil skirt.
2. A boyfriend cardigan + a pencil skirt + a t-shirt.  Add tights + flat ankle boots + jewelry of choice.
3. 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.
4. 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.
5. A red or other color drape-front cardigan + a black scoop-neck top over a black pencil skirt.  Add black tights + delicate gold necklaces.
6. 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.
7. A charcoal-gray cardigan + a blue-green t-shirt tucked inside a black pencil skirt.  Add tall black boots + crystal hoop earrings.
8. 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.

More Ways to Wear a Pencil Skirt

1. 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.
2. A silk blouse + a pencil skirt.
3. An animal-print silk top tucked into a black pencil skirt + a toned turtleneck.  Add nude heels + faux leather gloves.
4. A leopard-print top + a short black pencil skirt + a jean jacket.  Add jewelry + black heels.
5. A long-sleeve top over a pencil skirt.  Add a coin belt slung low on hips.  Push back sleeves.  Add a wristful of various colors and textures with narrow bangles on one wrist + a statement ring on the other hand.

   

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 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.
11. 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.

I hope I have inspired you with new ideas so that you can create a wider variety of  outfits and wear your pencil skirt more often!

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