How To Wear a Pencil Skirt If You Have a Midlife Middle
Nothing is sexier than a shapely pencil skirt that hugs your hips and bottom and says, “Yes, I’m a woman.” A pencil skirt can be your secret weapon if you want to walk into a room and look and feel powerful. Now, before you start moaning and groaning that it is impossible to wear a pencil skirt unless you are as skinny as a pencil, listen up!
Style Snapshot
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Shapewear smooths the tummy when wearing pencil skirts, especially with tucked-in tops.
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Pair pencil skirts with wrap tops, fitted sweaters, or jackets to balance proportions and camouflage the midsection, creating a well-defined silhouette.
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Choose pencil skirts with slimming details like dark colors, and vertical lines and opt for skirts that don’t taper too much at the knees for a more balanced appearance.
There are ways to wear a pencil skirt even if you have a softer, rounder, more mature body.
Start With Shapewear
Whether you are 1) fairly slim but have a bit of a midlife middle or 2) you are a round and curvy gal, a little shapewear goes a long way. If you want to wear a top tucked into your pencil skirt, consider investing in some Spanx. Shapewear works like a girdle but is as light as pantyhose. It firms your tummy, but it’s very comfortable. It will make a huge difference.
Try a Wrap Top
If you prefer to tuck in, a wrap top or a fitted top with some stretch and ruching works well to camouflage the tummy. 
A Sweater Can Help
If you’ve tried Spanx, but there’s still a bit of belly bulge you’d like to get rid of, try wearing a vest or sweater tucked out. Then add an oversized scarf, necklace, or earrings up top to draw attention to your face. Ensure your shirt has a well-defined shape. If it is just big and baggy, you will look sloppy. It should narrow slightly to give you that waist definition that is so important when wearing a pencil skirt.
A Cute Jacket Will Camouflage
If you are top-heavy in the chest and tummy, try tucking in and wearing a cute jacket over the top.
Other Ways to Look Slim in a Pencil Skirt…
- Make sure your skirt doesn’t pull or pucker. Buy a dress that fits your hips, then have it taken in at the waist to achieve the perfect fit.
- If you are a curvy hourglass, ensure that your pencil skirt doesn’t taper too much towards the knees once past your hips. This can make you appear unbalanced. If you are top
- Avoid pencil skirts with details at the waist, such as buttons, pockets, gathering, and trim. If you are a midlife mama with a jelly belly, these things will add bulk and make you look heavy.
- A dark pencil skirt is always more slimming than a light, bright, or patterned one.
- Pencil skirts with vertical lines, such as stripes, a slit, or a long zipper, draw the eye up and down, making you look long and lean.
- A pencil skirt with dark, color-blocked panels on the sides shaves off inches.
- A pencil skirt with a flared bottom or pleated bottom works wonders to draw eyes down to your pretty hemline and legs, which means you don’t have to feel self-conscious about your not-so-perfect middle.
Petites and the Pencil Skirt
What if you are short? Most pencil skirts end at the knee. You will want to show a little more leg to make your legs look longer, so aim for a couple of inches above the knee.
Do you wear pencil skirts? What are your tricks for getting a great look?
QUICK Q&A
Yes. Pencil skirts flatter all body types when styled correctly. The key is choosing the right fit, using shapewear if needed, and pairing with tops or layers that balance your shape.
Shapewear smooths the tummy and waistline, making tops easier to tuck in without bulging. It creates a firm, sleek silhouette that complements the slim cut of a pencil skirt.
Wrap tops, ruched fitted tops, or sweaters worn untucked work well to camouflage the midsection. Pairing them with accessories like scarves or statement jewelry also draws attention upward.
Skip skirts with waist details such as buttons, pockets, or pleats, as they add bulk. Instead, opt for dark colors, vertical details like zippers or stripes, or side color-blocking panels to look leaner.
Petites should choose skirts that end slightly above the knee rather than at the knee. Showing a little extra leg lengthens the silhouette, making the body look taller and more proportionate.
I liked most of the styling looks you showed. I’m making a new pencil skirt and summer jacket in the same fabric and wanted new looks for me in wearing the outfit together. Thank you for some excellent ideas.
I liked most of the styling looks you showed. I’m making a new pencil skirt and summer jacket in the same fabric and wanted new looks for me in wearing the outfit together. Thank you for some excellent ideas.
I am old school regarding keeping myself in shape, and I love wrap clothing. (Thank you, DVF) I recently purchased two black pencil skits, one in a heavier material and one with a lighter, sexier look. I will pair the heavier one with a blk and red polka-dot form-fitted sweater (5 yrs in closet, tag still on it), and the lighter one with a purple/blk/white geometric pattern wrap top and crystal accessories. Pencil skirts look sophisticated, show off a woman’s curves, and are a staple in a wardrobe. I shrunk out of my prior ones and just replaced them. I was a size six a while ago, now a 3. I’m petite.
I find pencil skirts to be the most flattering for my body shape. I have an apple shape (wide around the middle), but my hips and thighs are slim (relatively). The pencil skirt lets me show my best assets, and with an elastic waistband, it is comfortable and can be easily covered by a jacket. I have pictures on my blog at http://www.whenthegirlsrule.com if you’re interested.
I loved this article, and I am in my 30s! I love pencil skirts, but sometimes around “that time of the month, I want to look attractive still, but my waistline is retaining a ton of water, and it shows. This article has some great suggestions for dealing with that!
Thanks for answering my recent question about wearing skirts. I like your advice and respect your opinions. The styles are always trendy and classy, my preferred style. These models wear heels with skirts; could I substitute a boot during the winter months?
Hi Debbie, Yes, a tall boot with heels or a bootie would be fine. Something refined to go with the ladylike nature of a pencil skirt. Cheers, Deborah
So THAT’s what a pencil skirt is.