7 Steps to Nail the Tweed Skirt Trend That Diana Made Timeless

Princess Diana wore a tweed skirt in 1995. Michelle Monaghan just wore one to a pre-NYFW event. Three decades apart, same effortless polish. Curious how to make this classic work for you? Here’s your step-by-step guide.

1. Start with a matching set (or fake it)

The easiest way in? A coordinated tweed jacket and skirt. Michelle Monaghan chose Ann Taylor’s Collared Jacket in Tweed ($97) and matching Pocket A-Line Skirt in Tweed ($97). If a full set feels like too much, pair a tweed skirt with a solid blazer in a similar tone.

2. Choose your silhouette based on your vibe

A-line or pencil: Diana favored pencil skirts; Monaghan’s A-line is more relaxed. Both work.
Mini vs. midi: Minis feel youthful; midis read sophisticated. Pick what suits your lifestyle.

3. Stick to a simple shoe

Both Diana and Monaghan wore black pointy-toe pumps. That’s your safest bet. For a modern twist, try knee-high boots or a sleek loafer.

4. Keep the rest of your outfit minimal

Tweed is textured and eye-catching. Let it be the star. A plain tee, a tucked-in blouse, or a thin turtleneck keeps things balanced.

5. Play with color—but wisely

Diana’s skirt was bright; Monaghan’s leans neutral. A pop of color in the tweed (like pink, red, or blue) adds interest without overwhelming.

6. Shop smart: where to find great tweed skirts

Ann Taylor: Weekend Tweed A-Line Skirt, Pocket A-Line Skirt
Weekend Max Mara: Wool Blend Boucle Short Skirt
Cinq à Sept: Deva Birdseye Tweed Miniskirt
J.Crew Factory: Wool-Blend A-Line Mini Skirt

7. Wear it year-round

Yes, really. Tweed works in fall with tights and boots, in spring with bare legs and ballet flats. It’s the definition of transitional dressing.

Bonus: Why this trend never dies

Diana’s style endures because it’s rooted in quality and simplicity. A tweed skirt isn’t fast fashion—it’s an investment that outlasts trend cycles. So go ahead: channel your inner princess (or Monaghan) and step out in tweed. You’ll be in good company.

Ready to shop? Many of these pieces are still in stock—but not for long.

Source: https://www.whowhatwear.com/fashion/celebrity-style/michelle-monaghan-ann-taylor-red-skirt