What to Wear with a Plaid Dress?

I have an information overload on what to wear with a plaid dress. If I could, I’d take the time to list all the ways that Katy Perry, Kate Bosworth, Taylor Swift or Deepika Padukone, and countless other famous people rocked the plaid dress look they modeled. The ways to wear checked patterns I chose may serve you in a more practical way. 

Related: What to Wear with Plaid Pants? | What to Wear with Plaid Skirt? | What to Wear with a Plaid Jacket? | 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. Also, assume links that take you off the site are affiliate links such as links to Amazon. this means we may earn a commission if you buy something.

With Over-the-Knee Boots

This boot style may formalize your otherwise casual plaid dress in minutes. Maybe try ones made of flexible fabric to make them easier to put on and remove. I’ve seen them worn without pantyhose, even with dresses.

However, you could cover your legs if you want to. Some people might use this just in private with their intimate partners, but you can wear them out in front of people. Pop, rock and country performers, and actresses or models, do it all the time.

That’s one of the plaid dresses at has similar colors as one modeled in 2016, and the person wearing it has on the over-the-knee boots. I think this boot style would also look exquisite with black and white or gray plaid. However, I say, the subtler, the better when wearing a plaid dress for semiformal or formal occasions. One other over-the-knee idea: I imagine a bright yellow boot with a black and white checked dress.

With Thick Tights (or Leggings) With Feet

I like to wear tights with any dress because I feel self-conscious about my legs. Sometimes, I choose the thick, black tights with the feet on them instead of wearing leggings and socks that show my bare ankles. They serve a practical purpose, too.

It’s tough to always find a matching pair of socks in my house, so the thick tights with feet on them work the best for me. What’s more, I’ve hand-washed them, and it doesn’t take long for them to dry. I want to warn you, however, that nylon, polyester, or another rough fabric can irritate the skin. When I can, I prefer cotton tights or leggings.

With a Full Bodysuit

This solves any problems you could have with too low of a chest neckline or having to find a separate shirt for your second layer. I imagine not having to find any socks to match either. Of course, the major downside: You better be able to “hold it” for a while if you’re not near a bathroom. Garter belts and stockings attached to the top might work better, but you wouldn’t want them to show up through the fabric you’re wearing too much.

With a Denim Jacket

Using a denim jacket provides a fun way to make your drab plaid dress more alluring. Maybe even try a jean jacket with gems on it, or just stick to the basics. I wouldn’t want to go “too ‘80s” when wearing denim, however.

Choose your “big hair” decade jacket carefully or stick with 1970s, 1990s or 2000s versions, with few exceptions. I haven’t worn a jean jacket since high school, and I’d prefer the fitted ones now if I were to ever want one again.

My other option: I’d be willing to try perhaps a navy-blue jean jacket if I wanted to pair it with a red and navy plaid dress. The same idea would apply to red and black or black and white plaid, only I would choose a black jacket.

With Sneakers

For a casual look, try pairing your plaid dress with a denim jacket and sneakers. This combination sometimes seems “dorky” to me though. I don’t know why, but I always thought of pairing sneakers and socks with a dress as an odd thing to do. Maybe with oxfords if I were a middle school girl in a prep school that made me where a uniform. Otherwise, I probably wouldn’t.

Dress With Matching Shoes (Or Not!)

“We love the bold coordinated look, but even if you’re not ready to pair your plaids, taking either element of this set is a chic way to incorporate the trend into your fall wardrobe,” says E! News concerning Kate Bosworth.

You don’t necessarily have to wear the dress and shoes together all the time. However, it does cut down on shopping hassles if you can stand that much plaid in one outfit. If you do swap, you might want to try replacing the shoes in the original outfit featured on E! News with some that match the clutch accessory color.

These shoes and the dress I also picked out don’t resemble the original outfit that Kate wore in 2017. I figured it’s best to show you what’s available in 2022 or later. In this case, you might get away with matching shoes because the dress I chose doesn’t have much fabric.

For me, I’d probably choose a slit dress like the one the actress wore, even if it’s a “lot of gray.” Besides, I didn’t mention her outfit’s shoes: Bosworth has a striped, red bow tied on both ankles, and I think this does offset the excess of the gray a bit.

A Clutch Accessory

It probably doesn’t matter what clutch you choose if it somewhat coordinates with your outfit. I chose here this neutral one, that you maybe could pair with any of the plaid dress outfit examples I’ve shown you. However, I have mostly seen clutches for formal use or for when you want to dress up to go out to the club.

I came up with the first cutch idea after studying a little about what Kate Bosworth wore with her 2017 dress. However, I have yet to find a “boxier” shape like the one she had, which I prefer.

Of course, I had to choose a black clutch as a second alternative. This one, you can pair with just about any plaid dress color, whether a maxi, mini, midi – no matter the length. If the plaid looks too busy when trying with this clutch, try a satin or other solid, smooth textured purse.