How to Style Plaid Shirts

Plaid shirts are a staple in my closet. When there are days that I don't know what to wear, I tend to gravitate towards one out of my tiny collection. You can buy them fitted or oversized; from the men's department or even the kids' department. They also come in a variety of lengths, colours, patterns, and fabrics (cotton, flannel, wool, etc.). I decided to test the versatility of this shirt in another 'Dress with Jess' post (and left the accessories for your imagination). I hope you find some inspiration out of this!

P.S. Follow me on Instagram to see some "bonus" photos from this style session.
OCCASION: Dinner date
To dress up the casual shirt, I wore a blazer over it with a set of pointed heels. Since the all black look is pretty streamlined, I love that the pop of plaid draws the eyes to the centre. For a less dressy approach, you can remove the blazer and wear the top with just the leather leggings.

OCCASION: Lunch date
I love tucking my tops into this skirt because the flare gives an hourglass shape. Some flannels can look masculine, but when worn with the right pieces, you can add a little bit of girliness to it. Another great option for this look is wearing the plaid shirt as a crop top over a maxi dress.

OCCASION: Out with friends
For this outfit, I chose a colour (white) out of the pattern and wore it on the bottom. Wearing white jeans brings out the fine white lines in the shirt, which is a detail that few people would otherwise notice. I like the idea of tucking in the front half of your shirt into your jeans (or other bottom). It gives an outfit a more effortless look, which is a vibe I usually go for.

When I was in school, I usually wore flat shoes (but also wedges occasionally) because it was more practical for commuting, especially during rush hour. I like wearing my plaid shirts open with a tank top or t-shirt inside. You always have the option of buttoning it up if you feel cold, but even when I do button it, I do it half way up. You can also wear this outfit with leggings, but make sure your top is long enough to cover your bum!

OCCASION: Casual Friday at work
During the fall and winter months, layering is key to staying warm. If you want to, you can even add a blazer or flowy cardigan over this outfit for extra layers. I like how this look is polished enough to wear to work yet, there's also the option of removing the sweater afterwards if you're feeling too warm.

OCCASION: Shopping
Tucking in your shirt elongates the legs because there's nothing to cut off the length of your legs. Usually, I'd recommend wearing non-fuss clothing if you're going to the mall, but I'm not the type of person to try things on. Lining up and changing in/out of things is a hassle to me, especially in the colder months. I don't mind trying things on at home and exchanging/returning anything that doesn't fit. This is definitely an outfit I'd go shopping in because it feels comfortable to me.

I hope you guys liked this post! Comment below with your favourite (#1-6) outfit(s)!

Featured Plaid Shirts (all old/sold out)
Green plaid shirt via Jean Machine
Red plaid shirt via Forever 21
Blue plaid shirt via Gap Boys 

Sheinside boyfriend blazer

H&M leather pants (similar at ASOS)
Zara mid-heel court shoes 

Zara TRF mini skirt
ASOS hearts suspender tights
Call it Spring suede wedges

Old Navy Rock Star jeans (Marshmallow)
Zara mid-heel court shoes

T by Alexander Wang Classic Pocket Tank (Indigo)
Cheap Monday skinny jeans (Pitch Black)
Oasap pointed ankle Chelsea boots (c/o)

Joe Fresh striped sweater
H&M leather pants (similar by Velvet)
Zara mid-heel court shoes

Old Navy black leather belt
Cheap Monday skinny jeans (Pitch Black)
Report 'Abbott' leather over-the-knee boots

Shop plaid shirts
Other pieces from this post


  1. Great outfits! I love #s 1 and 5. I like how you styled different colors because I tend to see red plaid most of the time. I like these types of posts. Keep it up!

    1. Thank you for your continued support, Christine! I see red plaid more often than others, but it's actually my favourite colour of plaid right now. : )

  2. love how you were able to make it work for business wear, night out and everyday casual! :D

    Animated Confessions

    1. Thank you! I tried to make the pieces as versatile as I can. : )

  3. Curious about those leather pants... are they recent? How much and how do they fit? Thx!

    1. Hey, the leather pants are over a year old. I don't remember how much they were, but they were under $40 for sure. I'm wearing a size 2, which is my normal size at H&M. I actually saw a pair of leather pants there recently, so you should go and check them out!

  4. You look great! i don't have any plaided shirts that fit me perfectly, you make me want to go out and hunt for one

    1. You should try them out! They don't need to be super fitted because they can be worn casually. : ) Good luck!

  5. Love the freshness the white pants give in outfit #3!

    1. Thank you, Danielle! Glad you like it. : )

  6. Plaid shirt is more of like a tartan pattern.Ready to buying anytime.Explore Mens leather pants at an affordable price.