When contemplating what to wear with plaid shorts, I advise you not to overthink it. Usually, I see what’s out there and gain inspiration from how celebrities dress. Then, I combine those ideas with what’s available now.
Related: What to Wear with Plaid Pants? | What to Wear with Plaid Skirt? | What to Wear with a Plaid Dress? | What to Wear with a Plaid Jacket?
FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point.
With Tie Front Plaid Shorts
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My first example doesn’t involve a celebrity I know, but I think some tie-front plaid shorts I found may change up a boring summer outfit. Also, I learned from fashion expert Lori Bergamotto that some work environments may approve of tie-front shorts. She shares who the tie-front short would benefit the most.
“When you are someone who’s really petite … a little bit more volume is OK because what it does is helps define shape. And that’s what you’re really trying to do.”
I might hold out for a longer pair that reach the knees, but I like this business “chique” outfit I just discovered. The original outfit featured by Bergamotto showed blue silk tie-front pants. However, ideas of how to incorporate other clothing items with your tie-front shorts whether plaid or not, came to me from reading her suggestions.
The Top
The outfit has a blazer that matches the tie-front grey plaid shorts I found. Even if the specific example sells out before you can acquire it, at least it gives you an idea of how you can dress cool but remain professional.
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I found a second-layer shirt you could pair with the gray plaid tie-front short outfit. If you have black shirts, then skip looking for a new one if you want. Otherwise, find a few because they come in handy for outfit layering.
The Shoes
If you don’t think you can get away with open-toed sandals, try a closed-toe flat or heel instead. With or without pantyhose, these strapped sandals will accent your outfit, however.
With Cuffed Plaid Shorts
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I gained inspiration from Lindsay Lohan’s cuffed plaid shorts when I hunted for the ones I picked out. It’s not that I mind Lindsay’s shorts, but I sometimes prefer simpler checked patterns and bright colors. I decided to pick a different sweater and shirt for this outfit, however. If it were me, I also maybe would choose longer shorts, but I picked these to demonstrate the style.
The Top
For the shawl I chose instead of the original mint green cardigan, you could wear just about any fitted sleeveless or tank top shirt. However, that depends on if you want to wear it to the office or go on a family picnic or spend the day on the beach.
I like the way shawl cardigan sweaters accentuate my full figure, so I choose this over a tight-fitting cardigan. Besides, I wear shorts in the summer, not the winter. For shawls, I don’t care how long they extend, even if wearing shorts. After all, I sometimes wrap them or tie them.
The Shoes
You’re not limited to the close-toed, slightly chunky heels that Lindsay wore in her outfit. I decided on these chunky heeled sandals instead. However, I’m also going to present a flat option for walking outside long distances.
I suspect that if I were to wear this mint green plaid summer outfit that this strapped walking sandal would not make my feet hurt. It looks like it would conform to the feet well, which also accentuates the curvy style of the mint green shawl.
Bella Hadid Style
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In 2017, Vogue featured model Bella Hadid wearing a similar red plaid outfit as singer Justin Bieber. However, I chose a different pair than hers to not seem redundant. It’s a challenge to find the original made with all three colors of green, red and yellow, but it’s not impossible. That’s okay. It forces us to use our imagination when we can’t find the celebrity outfit replica.
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The original outfit featured a sweater that had a partially see-through region above the bust area. I believe the one I chose to replace it would provide more warmth in the winter, and I enjoy the texture that probably feels as soft and relaxing as it looks. If I could find one that resembles the look and feel of angora, however, I’d wear that over another shirt to keep me warm.
The Shoes
I’m not sure why famous people often come out of their limos wearing thin heels. I’d wobble when I walk if I had to enter onto the sidewalk like that. Bella’s shoes have one clear strap, but I chose all black. Now, I’m going to suggest a more comfortable walking shoe.
I wouldn’t want to walk down the street in thin heels, so I chose this walking shoe. It appears to provide comfort for at least a mile or so but looks classy enough to dress up a rather boring plaid outfit. If I didn’t mind wearing socks with shorts, I’d maybe instead wear sneakers like Justin did.
Justin Bieber Style
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You might find a similar red, green and yellow plaid version in 2022 similar to the one Bieber wore in 2017. The availability of specific lengths and fittings for differing body types might change from time to time. Virgil Abloh designed the Off-White brand shorts that possibly both Hadid and Bieber had modeled.
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Here we go – one of the simplest of summer star outfits I’ve seen for a while. It won’t be hard to find a men’s white T-shirt, and no one will probably notice if it’s not the same brand Bieber wore.
The Shoes
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I deviated from the white sneakers that Justin wore in 2017. I figured, why not? The blue stripe would coordinate well with the plaid shorts. You don’t have to take my advice though. There’s an infinite number of sneaker choices.
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John Mayer made his contribution to plaid in 2010. I know, that was more than a decade ago, but give me a second. Incidentally, Pop Sugar said he’s “mad for plaid and the Yankees.” Apparently, he compromised by wearing NY Yankee-colored plaid. The 2022 version I found don’t extend to near the knee and have smaller checks than the ones Mayer wore.
The Top
I found a shirt with two pockets on the front, but the pocket styles deviate a bit. Still, the overall piece may complement most navy checked short styles, preferably ones that come as close to the knee as possible. However, it would work with bottoms of any leg length.
The Shoes
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I picked a navy-themed active shoe instead of the one Mayer chose because I don’t understand. Why the brownish accent with a blue outfit? Maybe it’s to match his arm tattoo colors. I don’t know.
My problem is, I tend to only combine one solid and one busy texture or print together. I am too afraid of wearing the wrong shades, sometimes. I must have at least one color of any item I wear also appear in another piece, even if it’s just an accessory.