How to look your best in plaid over 40

#fashionover40 #fashionover50 How to wear plaid over40: example plaid skirt @ High Latitude Style @

What to look for when buying plaid items

Plaid is one of the woven pattern that has made its way into every style. The most important thing when buying a plaid item is to look for a great cut. The pattern should match at the seams. Otherwise every plaid item looks cheap as if you picked it up in the youth or children department. This is especially true for all of us who are wearing less than a US size 10. See here for a size converter .

fashion over 50 woman in Euro Chic twinset with plaid skirt
Front view of Euro Chic outfit with faux unmatched twin set made of Sofie cardigan and Moda International sweater worn with Burberry plaid skirt, studded pointy toe flats (all own), and jade-onyx necklace c/o Almo Jewellery

Since plaid works with every style, but Black or White Tie, plaid is perennial. The trend is just which of the plaid varieties is the most It in a season.

over 40 fashion woman with plaid bag
Back view of Jones New York silk shirt with eShakti lace skirt, Anne Klein slingback pumps, DIY bangle,  Paloma Picasso sunglasses, and Burberry plaid signature bag (all own)

Plaid in Euro Chic

Every Euro Chic fashionista associates the word plaid with Burberry (see photos above). Their classic lining for trench coats, their awesome signature scarf that we all want to have. Not to mention their plaid printed bags or rubber boots. <3 Who doesn’t wish to own a pair?

style over 50 woman in plaid blazer with belt and dress
Plaid in Euro Chic: Burberry plaid blazer with Kieselstein Cord belt, Hermes H-buckle, Ray Ban sunglasses (all own), and winter white V-neck dress c/o Lookbook Store

Euro Style embraces wool plaid for everything from blazers to skirts. Plaid in just two colors woven from cotton, i.e. gingham is a classic for summer button-down shirts and dresses. Brigit Bardot even wore a yellow gingham dress at her wedding. The shirts look awesome with capris and ballet flats, the dresses strappy, kitten or medium heel (2.5 inch, 5 cm) sandals.

style over 50 woman in gingham button-down shirt
Carhartt gingham shirt under eShakti jumper accessorized with brooches worn instead of a belt and Liz Clairborne open toe pumps, charm bracelet (all own), and wooden watch c/o Jord

Plaid in casual style

Every California Casual or American Southwest fashionista associates the classic plaid button-down shirt that looks great with jeans. The former has the high-waist, not too tight jeans with Birkenstock. The latter has the boot-cut jeans with cowboy boots. Both sometimes style their plaid shirt knotted around the waist or as a jacket over a plaid T-shirt (men’s department is welcome for high quality options with a more affordable price tag) which also makes a great style for open air concerts. Both sometimes add a hat, the Californian girl a trilby hat, the Southwest gal with a felt or leather cowboy hat.

ageless Style mature woman in plaid skirt
Plaid in casual posh style: Oliveo high-waisted linen pants with Oliveo plaid button-down shirt, Ray Ban Jackie O. sunglasses, Jaeger tote, Kieselstein Cord belt, H buckle, Anne Klein slingbacks (all own) and wooden watch c/o Jord

Plaid the Alaska street style way

The Alaska version of the plaid shirt is the plaid wool jacket cut like a straight button-down shirt, but from a coat-quality thick plaid fabric, two pockets on the breast, two diagonal pockets on the hips. No lining. It is worn with plaid lining jeans, duck boots, sweater, and trapper hat. While it is intended to be worn by men, women wear it too. Both genders prefer the red-black plaid with a little green.

#fashionover50 plaid shirt with denim skirt tights and sweater
Oliveo casual denim skirt with Oliveo button-down plaid shirt, GNW tight, Kieselstein Cord belt and buckle, L.K. Bennett patent leather pumps, lapsi and malachite beads necklace, Jockey white T-shirt, Hermes collier de chien bangle  and sweater knotted around the neck (all own)

Rock’n Roll and Punk

Here plaid pants are a big thing. Make sure the plaid pattern continues perfectly at the seams over the crotch. Otherwise you look like a clown. Also go for neutrals rather than the classic Rock’n Roll/Punk red and black. You want to be able to wear your wool pants to work, right? 😉

mature Fashion woman wearing a plaid dress
Plaid fit-and-flare dress c/o Voodoo Vixen paired with own GNW Luxe cashmere sweater, GNW tight, Hermes collier de chien bangle, and Clarks booties (all own) for a Rock’n Roll vibe style


Mod style is not just super-short mini dresses in A-line. Think argyle sweaters in three neutral colors or three colors of similar shade, or three neighbored colors on the color wheel. Style them with a corduroy neutral color A-line skirt and patent leather sandals in a bright color. What about the plaid blanket scarves? They are great to add an extra insulation layer in winter or cover-up on a chilly evening.

#fashionover40 mature woman wearing a argyle sweater over a sheath dress
Mod: L.L. bean argyle sweater worn over Elli Tahari sheath dress with Steven Mary Janes, Hermes collier de chien bangle, statement necklace, and Coach bag (all own) for a modern way to wear the Mod argyle

Argyle socks are a classic in work and casual style too in neutral colors under neutral color wool pants in winter or in bright colors under jeans with a solid neutral or bright sweater and sneakers on the weekend, respectively.

#fashionover50 woman in plaid skirt, sweater, cardigan and statement shoes

Bombshell and plaid

Even a bombshell like Sophia Loren or Marilyn Monroe looks great in a sheer neutral color plaid blouse with tie-neck paired with high-waist jeans, solid pencil skirt or trousers. Don’t forget the high-waist pencil skirt in black and white diamond weave with a sweater tucked in and high heel pumps! Or Victoria Beckham’s take on the bombshell with plaid in a black pencil skirt, plaid western skirt and sky-high heels. So sexy! <3

ageless Style mature woman wearing a plaid cape
Plaid cape worn over a shearling coat with gray GNW tights, Vince Camuto suede boots, hat, leather gloves, and 3.1 Philip Lim bag (all own)

Plaid in arty slick

A signature item in arty slick is the buttoned tailored plaid cape with pockets and collar. Go for brown with cream and black for ageless style. The plaid itself should look very wide with different widths from 2 to 8 inches (5 to 20 cm).

#styleover40 woman wearing a diagonal plaid A-line skirt with giraffe print sweater
Example layering top under giraffe print v-neck sweater with diagonal plaid A-line skirt, GNW tight and Gucci statement belt (all own)

Posh eclectic style and plaid

The Posh Eclectic style is the trickiest of all. To get this style right, you have to try out everything with everything and look for what looks the rightest way wrong. Think plaid and sequins, plaid button-down shirt with riding pants and wellies. you get the idea!

#midlifestyle women in office holiday party attire
Moda International sequin skirt with Oliveo plaid button-down shirt, Moschino belt, GNW tights, Hermes collier de chien bangle, and pumps (all own)
mature Style woman in plaid blazer with cargo pants
Orvis Irish plaid blazer with London Jean camouflage cargo pants, GNW Luxe cashmere sweater, smoky quartz statement belt,and Clark booties for a posh eclectic way of wearing plaid over 40 (all own)

I hope you liked the inspirations on how to wear plaid in an ageless style, no matter what style you are striving for. What is your preferred way to wear your plaid? Link it up tomorrow at the Top of the World Style fashion linkup party in addition to your outfit of the day. Note that you don’t have to have a blog to link up. You can also link to your Instagram posts or upload the photo. I would love to see how you wear your plaid.

If you found this post helpful tweet your friends the tips to look ageless in plaid. Then they owe you. Thank you. <3

fashion over 50 woman in plaid A-line skirt
Back view of A-line Burberry plaid skirt with Sofie cardigan, and flats (all own)

Get the support, motivation, and tips to look to your best in life. Get a subscription to High Latitude Style. Deep inside you know when I can do it you can do it too.

When you like the styling tips, you can get even more in my book How to Dress for Success in Midlife. Buy your copy now.

Photos: G. Kramm

Disclosure: This post has affiliate links

© 2013-2019 Nicole Mölders | All rights reserved