Old Money Lookbook: How to Style Plaid Clothing

Fab Sakker
by Fab Sakker
10 Minutes

There’s no denying that plaid clothing is a hallmark of the preppy style. Plaid, or tartan, has so much history and immediately looks really classic and classy.

I’m going to show you how to style plaid clothing to achieve an elegant, preppy style.

I’ll be styling a lot of green plaids because some are pieces passed down from my Scottish family clan, but you can get plaids in a lot of different colors that will suit your personal coloring and preference.

All of these tips work for all different colors! Let’s get started.

How to wear a plaid scarf

1. How to wear a plaid scarf

The first way to include plaid in your preppy wardrobe is super simple: a plaid scarf.

The one I’m wearing is vintage, so it’s a bit shorter than scarves you tend to see today, but it’s still so beautiful.

Once you have your plaid scarf, I encourage you to look at the colors in the plaid and pick some out that you’d like to accentuate. 

How to wear a plaid scarf

For example, I’ve chosen red and I’m going to tie it in with this red beret. It’s immediately so cute!

Don’t go too overboard with this. You don’t need a red bag or a red pair of shoes as well, but I’ve seen some really cool looks for this.

You might wear a red sweater underneath or pair red lipstick with the plaid.

There are lots of ways you can tie it in and incorporate it into your outfit.

How to wear a plaid scarf

A red scarf can also look really beautiful under a coat, jacket, or vest and peeking out over the top.

It just adds that little bit of pep to your outfit.

How to wear a plaid skirt

2. How to wear a plaid skirt

Next up, we have the plaid mini skirt!

This is such an adorable way to add plaid to your preppy wardrobe. For this skirt, I’ve chosen black to accentuate and popped on a little black tie with this blouse, which immediately gives preppy vibes.

I love popping a bow on with a blouse, especially if there’s a sweater over the top. It just looks adorable.

If you’re wearing a different color plaid, such as a red plaid, you could wear a red ribbon or red tie around your neck. 

How to wear a plaid skirt

I’ve gone for sort of a 60s vibe with this mini-skirt but you can also go with the miniskirts with the tartan that are sort of like a mini kilt and make those look preppy as well. 

How to wear a plaid skirt

Do be a little bit careful, though, because it can swing towards a 90s grunge vibe which isn’t what you want for the preppy style which is more refined and put together.

If you do choose a kilt skirt, pair it with something like a button-up or a turtleneck and bring in other elements of the preppy style to make sure you don’t get that swing.

How to wear a plaid dress

3. How to wear a plaid dress

The next item to include in your wardrobe is a plaid dress. Even though this dress is such a casual and easy dress, I immediately look a bit preppy and classic, so I highly recommend getting one.

A lot of companies sell button-down plaid dresses, but not many have one like this with a beautiful tie around it to cinch in the waist.

If you can’t find one, you can totally just grab a ribbon that goes with the dress and pop it around the waist. 

How to wear a plaid dress

The dress I’m wearing is quite a casual plaid dress, but there are so many beautiful, dressed-up evening dresses that are plaid.

How to wear a plaid kilt

4. How to wear a plaid kilt

Next up, we have the tartan kilt. The one I’m wearing is an authentic, Fergusson tartan kilt but so many brands do these mini-length skirts with a plaid print on them.

For this outfit, I’ve really made the kilt the focal point and I’ve just paired it with a black sweater, black tights, and black heels.

You can also wear ballet flats, but I think heels are best and they immediately elevate the look.

How to wear a plaid kilt

You can also wear over-the-knee boots that go all the way up underneath the kilt. Kate Middleton has worn pretty much that exact outfit but with a red skirt.

How to wear a plaid coat

The final item is a plaid coat. My coat is actually a puffer jacket, so it’s a bit more casual than if you chose a tailored coat, but they’re perfect for everyday wear because they’re so warm and it’s a super cute and preppy option over the athleisure wear or hiking puffer jackets. 

How to wear a plaid coat

For this outfit, I’ve gone super simple with a black sweater, black jeans, and black cowboy boots.

Cowboy boots aren’t really preppy, but they’re just a personal quirk. If you want to be more preppy, go for a pair of traditional riding boots. 

I would love to get a beautiful, well-tailored plaid coat like the style Kate Middleton wears as they’re just stunning.

How style plaid clothing

I hope you enjoyed this tutorial! Are there any other ways that you incorporate plaid clothing into your preppy wardrobe? Let me know in the comments down below.

Next up, learn about Kate Middleton's Casual Style and How to Dress Like an Off-Duty Duchess.

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