How To Wear a Plaid Shirt if You Tend to Hate Plaid Shirts

Okay, I can’t take full responsibility for the catchy title. Man Repeller recently published a post on wearing knee-length skirts when you hate them. Knee-length skirts do remind me of high school, but what’s worse in my book are plaid shirts. I won’t go on about how horrible they are. In five words, they make me look boxy. Or one: unflattering! But I love a challenge. And so, I recently bought a plaid shirt. Is there such thing as a flattering plaid shirt look for a pear/curvy shape? I’ll let you decide.

Outfit to dine at our favorite tapas restaurant, Pinxto Pote in Los Gatos: Current/Elliot® shirt / Julio top (old) / ATM silk charmeuse skirt – similar / Stuart Weitzman over-the-knee boots

Now I’ll be honest with you. We did this shoot in California, and I was freezing. Once we finished, I pulled on a short fitted jacket and a long wool coat. This is, however, what I wore indoors. As you can see, it’s quite suitable for indoor temperatures, with my plaid shirt layered over a long-sleeved top. My legs also stayed warm with over-the-knee boots under a silk A-line skirt.

I love the look of this plaid top with the rest of the outfit. That is, since I like blending styles and textures. I’m not one to dress a la grunge or lumberjack, but plaid gives my look a more laid-back vibe. I also discovered a nifty trick of using the sleeves of my long-sleeved (under layer) top as a cuff to secure my rolled-up shirt sleeves.

Flattering Way to Wear a Plaid Shirt

As for finding a flattering way to wear the plaid shirt, I relied on keeping the bottom unbuttoned and tying it in order to define my waistline. The high-waisted A-line skirt was also a big help. You can’t tell where my waist and hips actually are – and so, it creates a super slimming, long-legged silhouette.

In contrast, when I try this plaid shirt on – notice I don’t say wear! – with just jeans or trousers, my silhouette gets cut in half. On the top, my slimmest area is hidden by this awful rectangular shape, while attention is drawn to my hips, and…let’s just say it’s not pretty. The rectangular/square pattern of the plaid even seems to accentuate the boxiness.

Not a problem. Here are some alternatives to that look.

More Flattering Ways for a Pear-Shaped/Curvy Girl to Pull Off a Plaid Shirt

1. With skinny or narrow-legged jeans or leggings – I prefer them dark-colored – and a long open vest in a similar shade
2. Tucked into a high-waisted pencil skirt with pumps – another opportunity to blend styles
3. Under a long dark-colored blazer that cinches at the waist with pants or skirt in a similar hue
4. Worn open (like a jacket) over an all-black outfit – this works with a longer plaid shirt
5. Under a fitted sweater so that the collar, cuffs, and bottom pop out and with jeans, pants, or a skirt – if the plaid is of lighter colors, it can be a nice break from an all-dark outfit
6. Tied around the waist if you want a 90s-inspired look – with maybe a short straight skirt, top, and sneakers

If you’ve been avoiding plaid shirts because they just aren’t flattering, I hope that I’ve given you some ideas to get back on that horse. That is, if you – like me – don’t want to be barred from this classic shirt style. Do you wear plaid shirts, and if so, what is your favorite way?

XO, Janea

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