What to wear with a plaid jacket, that is the question. Hint: One of my ideas does not involve pairing them with 1980s sweatpants. You probably could get away with that though.
Related: What to Wear with Plaid Pants? | What to Wear with Plaid Skirt? | What to Wear with a Plaid Dress? | What to Wear with Plaid Shorts?
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.
Plaid with Fold-Over Jeans
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“Another day, another fall trend for a Hadid sister,” says E! News reporters about model Gigi Hadid’s plaid walking outfit. I’d want a bit more room in the abs area if wearing the fold-over jeans featured in this plaid ensemble in 2019, a pant that originated from the 1980s. Other than that, this flannel with the fold-over jeans appears to provide comfort and warmth on the fall day when Gigi wore it.
The Jacket
Updating the 2019 outfit featured by Gigi for relevance in 2022 and beyond won’t take much effort. I’ve seen a multitude of classic red and black plaid jackets and oversized shirts used for both style and warmth. The example I found only represents a fraction of options still available today.
The Second Top Layer
Gigi’s original outfit appears to have a black turtleneck shirt as a layer under the plaid. However, I avoid wearing tight collars whenever possible, so I decided to pick a simple, long-sleeve, crew neck black shirt. Fitted, black long-sleeve shirts have become a layering wardrobe stable for me, and I wear them often.
The Shoes
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The upper slip-on shape of my first selection appears similar to the one Gigi Hadid wore with her outfit in 2019. The one I picked out has a matte instead of a shiny surface though. This shoe I chose, however, may provide an extra cushion when walking for blocks while running errands in a large metro city.
I’ve seen fold-over jeans put together with different sandal heel styles. I’d prefer these thick heels for steadiness while walking. However, others have a single wide strap and stiletto or pump heels.
Here’s a switch. I grew up in the 1980s-1990s, so I know that most people at that time wore jeans with sneakers when attending school classes. Sometimes, wearing sneakers instead of dress shoes or heels also makes sense for most outdoor – and even some indoor casual social events.
Plaid with Lounge Pants
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I didn’t intend to use the same celebrity for two examples, but Gigi appeared at the JFK airport in March 2020 wearing what looks like light beige loose-fitting trousers or lounge pants. Hers had flannel front panels added to them, but I chose a simpler pair. You might not find Gigi’s online and may have to acquire them a different way.
The Jacket
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Gigi’s choice of plaid jacket from her 2020 JFK airport arrival impressed me more than her pants. On the other hand, I visualize evergreen prevailing against changing fall leaves when I look at my alternate selection. I can’t think of a better fall jacket choice, but the green in it makes it all-season outerwear.
The Second Top Layer
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I love thin, vertical stripes on a button-down, butterfly collared shirt. For me, the navy would accommodate me well, whereas my hair color resembles Gigi’s. However, it’s possible to wear any colored top with neutral trousers and brown boots.
The Shoes
The conditioned brandy-colored walking boots I found would coordinate with either the jacket Gigi wore at the airport, or the green checked one I picked out. The ultra-shiny, black ankle boots originally modeled with “my” jacket don’t seem to blend well with the matte, woollike coat texture. That’s why.
Plaid with Carpenter Pants
In December 2021, Dax Shepherd wore a red plaid jacket, carpenter jean and sneakers ensemble while on a weekend getaway with wife Kristen Bell and friends. The contrast between his casual and her formal attire caused me to chuckle a bit.
The Jacket
Did you notice that the plaid Dax wore on his getaway with Kristen comes in a brighter red shade than most? I haven’t decided if I personally like it, but it made sense to me after I noticed the second top layer and his shoes.
Who am I to think I can dress a celebrity better than a professional stylist? Just “hear” me out though. If I were to catch myself wearing those orange-trimmed sneakers that I’d at least want to add a jacket with the same color. Thus, I show you one of the multitudes of available orange plaid jackets I found.
The Second Top Layer
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I don’t usually do collars that feel too constricting. However, the shirt Dax wore could keep the neck warm. Still, I’d probably choose one without the “neck” part.
I wouldn’t need the shirt underneath my button-down plaid jacket to show, so I’d probably wear just a long-sleeve shirt with no turtleneck. Long-sleeve shirts come in just about any color, including the pink or orange that would match Dax’s shoes — or in dark or light, multipurpose shades.
The Shoes
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I’m not sure why Dax Shepherd would wear white sneakers with orange trim. Why not black and white or red and white with the classic plaid? Well, there’s at least some red in the second swish that serves in the shadow of the first swish on the shoe sides.
Part of the wedge also has red in it too, but why the orange? If you notice, Dax also has on an orange turtleneck under his bright red plaid jacket.
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I’m not much for sneakers when walking out in nature, even in a desert instead of a forest. Just for fun, I show an example of what a black hiking boot would look like with orange laces. This could match Dax’s orange turtleneck.
Plaid with Skinny Pants (or Jeans)
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“The staple denim isn’t immune to trends just because it has seniority over newer styles,” says Anna Laplaca of Who What Wear. This doesn’t mean that the skinny pant or jean will always remain the most popular. However, skinny pant styles probably have become as classic as the little black dress or white sneakers.
The Jacket
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You’re not limited to just red and black plaid jackets. I like this long trench coat style black and white checked jacket, with similar features as the actor and producer Micheal B. Jordan wore in New York in 2018. A version sold in 2022 has the shape and length as the 2018 one but has vertical instead of horizontal pockets.
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The press also snapped pictures of Micheal B. Jordan wearing the classic red and black plaid. This checked statement coat extends past the knees, and I found it customized for a variety of male and female figures. It adds extra insulation over his all-black outfit with a hoodie underneath it.
When looking for a black hoodie that would go underneath the red statement coat Michael wore, I came across this plaid jacket. It’s one of few that I’ve seen with a built-in hood and lining. I’m thinking of buying one like it for chilly days.
The Second Top Layer
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Under the long, black and white checked trench coat, Micheal B Jordan rocks a striped crewneck sweater similar to this one. There’s room in this coat for more layers, such as an oxford or turtleneck shirt.
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Jordan appears to have a high-end hoodie under his red statement coat. The inside hood lining of his may be blue, gray or another light color. I chose a style close to it available in 2022.
The Shoes
Who wants a shoe from 2018 if they can have one still made in 2022? This shoe I picked out will work just as well as the one Michael wore, or any thick heeled boot or high-top cut would complement this outfit.