Presenting Princess Diana’s 12 Best Plaid Outfits for Your Autumn Style Inspiration ~ ANIO AMAG

Presenting Princess Diana's 12 Best Plaid Outfits for Your Autumn Style Inspiration Emily BurackOctober 5, 2025 at 5:00 AM 0 "Hearst Magazines and Yahoo may earn commission or revenue on some items through these links.

- - Presenting Princess Diana's 12 Best Plaid Outfits for Your Autumn Style Inspiration

Emily BurackOctober 5, 2025 at 5:00 AM

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

It's no secret that royal women love to wear a plaid print—and the late Princess Diana was no exception. In fact, Diana turned to plaid frequently throughout her life wearing wearing it at both casual outings and black tie events. Here, 12 of Princess Diana's best plaid outfits for fall 2025 style inspiration—and how to recreate her looks:

1. Classic tartan coat

Diana on a visit the Château de Chenonceau on the River Cher in France, November 1988. Princess Diana Archive - Getty Images

To start, when thinking about autumnal dressing, a wool coat is an essential. Princess Diana stepped out in a tartan coat-dress by Catherine Walker in 1988, and rewore it again the following year. Here, some options from Ralph Lauren, Barbour, Sézane, and more:

Double-Breasted Black Watch Plaid Coat

380.00 at ralphlauren.com

Gislene Plaid Virgin Wool Coat

835.00 at saksfifthavenue.com

Beattie Double Breasted Coat

$690.00 at bloomingdales.com

Viktor Coat

455.00 at sezane.com

Check Bouclé Coat

$3750.00 at burberry.com

Khaki checked double-face double-breasted coat

$555.00 at bimbaylola.com

2. Mockneck dress

Diana, 1981. Anwar Hussein - Getty Images

Princess Diana's best plaid style moments came not in fall, but each summer at the Braemar Highland Games in Braemar, Scotland. For her first appearance at the games, in 1981, she chose a tartan dress designed by Caroline Charles, pairing it with a black tam o'shanter style hat. There are a few ways to take style inspiration from Diana here: either opt for a long-sleeve dress, or one with delicate embellishments—or both!

Seraphine Dress

$298.00 at shopdoen.com

Ghospell check print dress

$43.20 at us.asos.com

Hazel Long Sleeve Midi Dress

$180.00 at damsonmadder.com

Plaid Tiered Shirtdress

398.00 at ralphlauren.com

Briar Plaid Long Sleeve Minidress

$140.00 at nordstrom.com

Venetia Dress

1490.00 at net-a-porter.com

Renes Maxi Dress

725.00 at modaoperandi.com

Draped Dress

$695.00 at bloomingdales.com

Cassie Check Tea Dress

199.00 at us.boden.com

3. Black and white tartan

Diana at the 1989 Braemar Games. Princess Diana Archive - Getty Images

Diana's black and white tartan dress by Catherine Walker was another standout Scottish look for the late royal. Evoke her outfit by opting for a black and white plaid print from designers including Norma Kamali, Burberry, and Brandon Maxwell:

Belted jersey midi dress

512.00 at mytheresa.com

Mairead Check Plaid Maria Dress

328.00 at tnuck.com

Check Short-Sleeve Crinkle Midi Dress

$1650.00 at Bergdorf Goodman

Black & White Tartan Maxi Dress

210.00 at ssense.com

Calypso Dress

748.00 at revolve.com

Rory Jacquard Plaid Trumpet Midi-Skirt

$1480.00 at saksfifthavenue.com

4. Plaid skirt

Diana leaves the Young England kindergarten, October 1980. Hulton Archive - Getty Images

You don't have to wear head-to-toe plaid; the busy print can add a pop of interest to your outfit, like Diana showed in her pre-royal life with this purple skirt and black sweater combo. Luckily, there are plenty of skirts of all lengths to shop, from Burberry's wool midi option to a mini wrap skirt from Loewe:

Check Wool Blend Midi Skirt

$1995.00 at burberry.com

Women's Pleated Check Skirt

$1850.00 at saksfifthavenue.com

Saskia skirt

$348.00 at shopdoen.com

Textured Plaid-Print Pleated Midi Circle Skirt

$2090.00 at bergdorfgoodman.com

Hayley Wool Midi Skirt

$229.00 at boden.com

Tweed Plaid Miniskirt

$625.00 at saksfifthavenue.com

Mini Wrap Skirt

1800.00 at net-a-porter.com

Chiffon Plaid Skirt

288.00 at brooksbrothers.com

Nicole Plaid Cotton Skirt

$390.00 at nordstrom.com

5. Contrasting collar

Diana in Scotland, 1982. Tim Graham - Getty Images

Back at the Braemar Highland Games in 1982, Diana again chose a long-sleeved dress—but this one featured a contrasting collar, a chic style element that can be found on many plaid dresses in 2025. (Diana was, once again, ahead of her time!)

Saige dress

395.00 at net-a-porter.com

Darby Plaid Cap Sleeve Mini Dress

371.00 at bloomingdales.com

Prince of Wales checked tweed mini dress

600.00 at net-a-porter.com

Rachelle Mini Dress

$98.00 at revolve.com

Rhinestone Check Shirt

$365.00 at saksfifthavenue.com

Ellis Check Minidress

198.00 at saksfifthavenue.com

6. Eveningwear, but make it plaid

Plaid and black tie don't necessarily go hand-in-hand but as Princess of Wales, Diana stepped out in a few plaid gowns, including a Catherine Walker tartan evening gown in 1991:

Diana in a Catherine Walker design. Anwar Hussein - Getty Images

And a red chiffon Bruce Oldfield dress embroidered with a silver tartan design for the London premiere of When Harry Met Sally in 1989:

Diana in a Bruce Oldfield dress. Tim Graham - Getty Images

While plaid gowns aren't as easy to come by, if you're looking to lean into the style for, say, a fall wedding, here are some chic options:

Tartan Tie Waist Sleeveless Satin Gown

$325.00 at nordstrom.com

Plaid Georgette Tiered Tie-Neck Gown

$295.00 at ralphlauren.com

Lana Gown

610.00 at sachinandbabi.com

Wavy Plaid Stretch Cotton Bustier Dress

$4890.00 at nordstrom.com

Check Silk Wrap Dress

$3250.00 at Burberry

The Evette Mock Neck Evening Dress

$180.00 at nordstrom.com

7. Unexpected colors

Diana wasn't one to shy away from bold style statements—and her tartan pieces were no exception. Take this dress she wore visiting Venice in 1985:

Tim Graham - Getty Images

Or this bold yellow and black check coat designed by Escada (featuring a matching hat designed by Philip Somerville) in Berlin in 1987:

Anwar Hussein - Getty Images

Plaids, Diana proved, don't have to be in muted autumnal tones. They can be in blue (see: L'Agence, Proenza Schuler) or yellow (Markarian, Bottega Veneta) or green (Celine)! Here, some stylish unexpected plaid colors:

Patrica Plaid Slit Maxi Skirt

$357.00 at saksfifthavenue.com

mini shirt dress in check wool natté

$3850.00 at celine.com

Pleated paneled checked cotton midi dress

4300.00 at net-a-porter.com

Margot Dress

$598.00 at dvf.com

Women's Giorgia Plaid Cotton Midi-Dress

$1595.00 at saksfifthavenue.com

Hallie Crinkled Plaid Dress

1490.00 at bergdorfgoodman.com

8. Prince of Wales check

Diana in September 1989. Tim Graham - Getty Images

Fittingly, as Princess of Wales, wore many pieces that featured the Prince of Wales check (also known as "Glen Plaid," as it originated the Glenurquhart Estate in Inverness-shire, Scotland). Here, some modern takes on the pattern from Veronica Beard, St. John, Brunello Cucinelli, and more:

Vaena Prince Of Wales Check Double-Breasted Blazer

298.99 at saksfifthavenue.com

The Prince of Wales Plaid Tulle Top

$760.00 at nordstrom.com

Double-breasted Prince of Wales checked tweed blazer

$315.00 at theoutnet.com

Prince of Wales Plaid Midi Skirt

$795.00 at nordstrom.com

Javia Plaid Jacket in Prince of Wales Merino Wool

$438.00 at fbrq.com

Prince of Wales Blazer

$5700.00 at nordstrom.com

Prince of Wales Check Cool Wool Blouse

$1780.00 at bergdorfgoodman.com

The Sophie Crew Neck Fitted Mini Dress

$1650.00 at shopbop.com

Prince of Wales checked tweed midi skirt

279.00 at theoutnet.com

9. Skirt suit set

Diana visits the St Helen's Rugby Club in Swansea, Wales. Princess Diana Archive - Getty Images

Long before Taylor Swift was wearing plaid skirt suits to Kansas City Chiefs games, Princess Diana wore wearing a red and black tartan suit in 1992. If you're going to wear plaid, why not wear it in a matching set?

Bethany Houndstooth Blazer

$695.00 at lagence.com

Pilar Houndstooth Wide-Leg Pant

$475.00 at lagence.com

Maisey Blouse

248.00 at shopbop.com

Lydia Skirt

298.00 at shopbop.com

Kendryn Embellished Dickey Jacket

$998.00 at veronicabeard.com

Pavaline Houndstooth Mini Skirt

$428.00 at veronicabeard.com

10. Pretty in pink

Diana in August 1992. Mirrorpix - Getty Images

While pastel colors are not necessarily associated with fall fashion, the plaid print makes the palette more acceptable for any season—particularly if you're looking to embrace some autumnal prints in warmer climates.

Lucky Picnic Dress

925.00 at shopbop.com

Plaid Tweed Minidress

$112.00 at nordstrom.com

Women's Checked Cotton Midi Skirt

$2200.00 at saksfifthavenue.com

Fuzzy Scarf

$320.00 at nordstrom.com

Plaid Sleeveless Tweed Minidress

$1890.00 at nordstrom.com

Dale Dress

148.00 at thereformation.com

11. Festive plaid

Diana in November 1991. Anwar Hussein - Getty Images

Princess Diana wore this red and green tartan coat dress designed by Catherine Walker at least twice—and surprisingly, neither of the appearances were on Christmas. Still, as we get closer to holiday season, green and red plaid pieces are a fun (and festive) way to take a style cue from the late princess.

Checked Plaid Georgette Tie-Neck Blouse

145.00 at ralphlauren.com

Plaid Mary Jane in Black/Red

$325.00 at nordstrom.com

Cecelia Wool Skirt

$199.00 at boden.com

The Virginia Jacket

$99.00 at hillhousehome.com

Red & Green Pulling Midi Dress

$555.00 at viviennewestwood.com

Recycled Classic Plaid Scarf

$95.00 at nordstrom.com

12. Accessorize with plaid!

Note the plaid bows on her shoes! Princess Diana Archive - Getty Images

Last but not least, Princess Diana understood the power of a smart accessory—like the bows on her shoes during an engagement in Australia in 1985. Put a plaid spin on your shoes, hats, or handbags this fall:

oversized bow clip - multi check