Plaid is one of those timeless patterns, like polka dots, stripes or leopard print, that you know will never date, so investing in a pair of plaid pants makes sense. But what to wear with plaid pants? Below, you’ll find stylish plaid pants outfit choices for everyday…

Take a look, you might just be inspired to swap your black pants or jeans for some checks.

What to think about when putting together a plaid pants outfit

Plaid pants outfit ideas - Shauna wears check pants and a sweater | 40plusstyle.com

Because the print runs both up and down, and across, plaid pants can make your bottom half look wider. This may be a tricky look to wear if you’re a pear shape. However, you can definitely make it work for you. For example, you could wear a wide leg pair of plaid pants to skim over your thighs and hips and then choose a bright red top to draw the attention upwards.

If you’re an inverted triangle, plaid pants could be perfect as they can balance out your wider shoulders.

Shauna @chicover50 (read her style interview here) wears a pair of plaid pants that are effective at elongating the legs as they have a dominant vertical stripe.

Recreate her outfit with this similar sweater, plaid pants, sneakers and beanie.

Best plaid pants for your plaid pants outfits

Before looking at what to wear with your plaid pants, do you already have a pair? Or will you be adding a pair to your closet this season? If you’re treating yourself to a new pair, you’ll find some of the most recommended below…

Lee motion fit plaid pants

For a subtle take on the plaid pants trend, you could choose a mixture of black and gray like the Lee pants (below) which are made with flexible fabric for comfort. Reviewers say these are a good choice for work if you need to go into the office.

Lee Flex Motion Regular Fit Trousers | 40plusstyle.com

Lee Flex Motion Regular Fit Trousers

black plaid pants

For a versatile pair of check pants that would be ideal for work or casual days, you could try the Grace Karin elastic waist pants (below). Wear with a t-shirt and sneakers for the weekend or with pumps and a blouse for work. Reviewers say these are light, breathable and have a decent amount of stretch.

GRACE KARIN Elastic Waist Plaid Pants | 40plusstyle.com

GRACE KARIN Elastic Waist Plaid Pants

Check flare pants

Wide leg pants are particularly on trend at the moment. The Karen Millen pants (below) have a classic country check and will look good with heeled booties.

Karen Millen Check Wide Leg Trousers | 40plusstyle.com

Karen Millen Check Wide Leg Trousers

Drawstring pants

For lounging or working from home, a pair of drawstring pants is a comfy, stylish option. You could choose a block color top or opt for a graphic t-shirt and mix your patterns.

Treasure & Bond Plaid Drawstring Pants | 40plusstyle.com

Treasure & Bond Plaid Drawstring Pants

Plaid cargo pants

Lands’ End often has a good selection of plaid pants. The utility style drawstring pants (below) have a casual style that would look good with sneakers. To elevate the look, you could wear a blazer over the top.

Lands' End Sport Knit High Rise Cargo Ankle Pants | 40plusstyle.com

Lands’ End Sport Knit High Rise Cargo Ankle Pants

Pull on pants

Plaid pants outfits - Fonda wears check pants and a cardigan | 40plusstyle.com

Fonda @savvysouthernchic above chooses a pair of green and blue check pants and adds neutral accessories to her plaid pants outfit.

Check out this similar top, cardigan, pants, boots, fedora and necklace.

You could also try a pair of pull-on plaid pants in black and white like the Lands’ End pants below.

Lands' End Sport Knit High Rise Elastic Waist Pull On Pant | 40plusstyle.com

Lands’ End Sport Knit High Rise Elastic Waist Pull On Pants

Wide leg pants

If you want to make a real style statement, then a very wide pair of check pants will definitely get you noticed for the right reasons. Tuck your top into your pants to make your legs look longer.

Floerns Plaid Print High Waist Wide Leg Pants | 40plusstyle.com

Floerns Plaid Print High Waist Wide Leg Pants

Sutton pants from Loft

If you like to wear skinny or slim pants, you could get a different look for your day-to-day outfits by choosing a print. You could wear a longer tunic or white shirt over the top.

LOFT Sutton Skinny Pants In Plaid | 40plusstyle.com

LOFT Sutton Skinny Pants In Plaid

Plaid jogger pants

The line between activewear and workwear is definitely being blurred with so many people working from home. You could wear the jogging pants (below) with a blazer and heels or with sneakers and a moto jacket.

LOFT Plaid Jogger Pants | 40plusstyle.com

LOFT Plaid Jogger Pants

ankLe pants

A pair of ankle pants can be perfect for transitioning from winter to spring. You can show off a little ankle without losing too much warmth. Wear with ballet flats or heeled sandals.

A New Day High-Rise Skinny Ankle Pants | 40plusstyle.com

A New Day High-Rise Skinny Ankle Pants

Allegra K pants

While it tends to be easy to find black and white plaid pants, if you want a different color, the Allegra K pants (below) are worth a look. They come in a good choice of shades and print like the neutral checks shown here. Reviewers say these have a relaxed, baggy fit.

Allegra K Plaid Elastic Waist Trousers | 40plusstyle.com

Allegra K Plaid Elastic Waist Trousers

Skinny check pants

The Wdirara skinny pants (below) could work well worn with an asymmetrical tunic or a long white shirt. They come in a wide range of check styles and colors. Reviewers say they feel like leggings but look like trousers.

WDIRARA Stretchy Plaid Print Skinny Regular Pants | 40plusstyle.com

WDIRARA Stretchy Plaid Print Skinny Regular Pants

Plaid palazzo pants

For a wide pants option, you could try the high waist palazzo pants (below) which reviewers say work well for women with curves.

Tronjori High Waist Wide Leg Palazzo Pants | 40plusstyle.com

Tronjori High Waist Wide Leg Palazzo Pants

Slim fit pants

The pull-on pants (below) come in a gray plaid or a subtle brown houndstooth. Reviewers say they feel as comfortable as leggings but look like dressy work pants.

Van Heusen Super Stretch Slim Fit Pull-on Pants | 40plusstyle.com

Van Heusen Super Stretch Slim Fit Pull-on Pants

Plaid pants outfits

Now that you’re thinking about your favorite pair of plaid plants – either to add to your closet or a pair you already have, what will you wear with them? How will you put together your plaid pants outfit? Let’s take a look at some outfit ideas.

Outfit 1: with a blazer

Boma wears check pants and a blazer | 40plusstyle.com

A blazer looks great over pretty much everything. Boma @mrs.gaf above wears her black blazer over her check pants and adds a pop of color with her orange bag.

Recreate her outfit with this similar blazer, pants, clutch and pumps.

Plaid pants with a blazer | 40plusstyle.com

Urban CoCo Open Front BlazerBoden Silk ShirtLands’ End Sport Knit High Rise Elastic Waist Pull On PantClarks Linvale Sea Ankle BootieKurt Geiger London Violet Leather Tote

Outfit 2: with a trench coat for a classic look

A pair of plaid pants is an absolute classic, so it makes sense to wear them with other classic clothes and accessories like a trrench coat and tote bag.

Also, take a look at how to put together a capsule wardrobe for the classic style personality.

Plaid pants with a trench coat for a classic look | 40plusstyle.com

Cole Haan Signature Hooded Trench CoatBoden Silk ShirtKaren Millen Check Wide Leg TrousersClarks Linvale Sea Ankle BootieKurt Geiger London Violet Leather ToteVIENNOIS Round Dangle Earrings

Outfit 3: with sneakers for a casual look

Yvonne wears check pants and sneakers | 40plusstyle.com

Check pants are incredibly versatile. You can wear for work or dinner, or casually with sneakers like Yvonne @funkyforty above (read her style interview here).

Steal her look with this similar shirt, coat, pants, sneakers, belt and sunglasses.

Plaid pants with sneakers for a casual look | 40plusstyle.com

BLANKNYC Cotton Blend French Terry CoatGIBSONLOOK Side Ruched TopLands’ End Sport Knit High Rise Cargo Ankle PantsDr. Scholl’s Shoes Wander Up SneakerCLUCI Leather Backpack

Outfit 4: with a poncho

A stylish look to keep you warm can be to wear your knitwear in layers with your check pants. Opt for a poncho worn over your turtleneck.

Plaid pants with a poncho | 40plusstyle.com

COS Wool PonchoMixMatchy Lightweight Turtleneck TopGRACE KARIN Elastic Waist Plaid PantsDr. Scholl’s Shoes Wander Up SneakerCLUCI Leather BackpackVIENNOIS Round Dangle Earrings

Outfit 5: with heels for a night out 

Kim wears heels with her plaid pants | 40plusstyle.com

Kim @kimair above (read her style interview here) shows how you could mix formal and informal for a stylish look. She wears her check pants and sweater with dress pumps.

Get her look with this similar sweater (other options here and here), pants, pumps, bag and sunglasses.

Plaid pants with heels for a night out | 40plusstyle.com

Veronica Beard Fawsett Off the Shoulder TopKaren Millen Check Wide Leg TrousersLifeStride Charlotte Heeled SandalJNB Envelope ClutchVIENNOIS Round Dangle Earrings

Outfit 6: with a tunic

If you choose a pair of skinny or slim pants, a longer tunic will look great with them. To add interest, choose an asymmetrical top.

Plaid pants and tunic top | 40plusstyle.com

Esenchel V-Neck Swing Tunic TopLands’ End Sport Knit High Rise Elastic Waist Pull On PantsClarks Linvale Sea Ankle BootieJNB Envelope ClutchKendra Scott Tassel Bolo Necklace

Outfit 7: with a cozy sweater for a preppy look

Sylvia wears a preppy plaid pants outfit | 40plusstyle.com

Plaid pants can be the perfect choice for a classic style as well as looking good as part of a preppy outfit like that of Sylvia @sylviacolella above (read her style interview here)

Get her look with this similar sweater, pants, loafers, bag and sunglasses.

Plaid pants with a cozy sweater for a preppy look | 40plusstyle.com

Cole Haan Signature Hooded Trench CoatRails Halle Cashmere & Merino Wool Blend SweaterGRACE KARIN Elastic Waist Plaid PantsKurt Geiger London Violet Leather ToteFranco Sarto Carolynn Loafer

Outfit 8: with a short jacket

Playing with proportions can add interest to your outfit. Try a shorter jacket worn over a longer tunic.

Plaid pants worn with a short jacket | 40plusstyle.com

Thread & Supply Crop Fleece Shirt JacketLARACE Flare Tunic TopLands’ End Sport Knit High Rise Elastic Waist Pull On PantsFranco Sarto Carolynn LoaferCLUCI Leather Backpack

Outfit 9: with more checks

Timeless plaid pants outfit ideas: What to wear with plaid pants | 40plusstyle.com

While an easy outfit choice can be to team a pair of check pants with a block color top, you could also combine your checks. Carmen @carmen_gimeno above looks stylish and modern in her check suit and sneakers.

Check out this blazer plaid set (another option here) that you can wear with this similar turtleneck top, sneakers and handbag.

Plaid pants paired with more checks | 40plusstyle.com

BB Dakota by Steve Madden Check You Out CoatRails Halle Cashmere & Merino Wool Blend SweaterTreasure & Bond Plaid Drawstring PantsClarks Linvale Sea Ankle BootieJNB Envelope ClutchVIENNOIS Round Dangle Earrings

Plaid pants capsule wardrobe | 40plusstyle.com

shop some of the items above here:

Do you already have a pair of plaid pants in your closet? What do you style yours with? And do you tend to save them for one particular season? You can let me know in the comments below?

Continue reading:

  1. How To Wear Jeans Over 40 – Guidelines And Lots Of Ideas
  2. The Best Pants And Skirts To Fit And Hide Your Belly
  3. How To Wear Leggings Over 40 – A Complete Guide With The Best Leggings And Tops And Shoes To Wear With Them

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Timeless plaid pants outfit ideas: What to wear with plaid pants | 40plusstyle.com

Feature image by Carmen @carmen_gimeno

Sylvia

Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. She is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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