You are currently viewing How to Style a Shirt: 1 Shirt, 3 Looks

There’s not much better, in my opinion, than a piece of clothing that you can have for a long time and still be excited to wear it. That’s how I feel about a chambray shirt that I bought a year ago. At the time of purchase, a chambray top felt like a classic investment and even though a button up shirt didn’t really feel like “me”, I had been obsessing over this particular style for a while. To quote myself at the time: 

“I don’t own any button up blouses because they don’t feel like “me”. Part of the reason is that I don’t like collars … I love anything chambray and since it doesn’t have a collar, I figured that it was worth a try and I love it.”

Amazing how all of these things still apply. I still feel like collared shirts aren’t “me” but I have made an effort to embrace them more. And I still love this shirt.

1 Shirt, 3 Looks

So, in the name of sustainable fashion and loving the things that we own, in spite of all the new, shiny things that we are constantly bombarded with, I thought it would be fun to style a shirt that I already owned 3 different ways. I’ve done this in the past with a skirt, a jumpsuit, and a dress. It really helps me to see the versatility of a piece of clothing.

I’ve included this shirt in my fall capsule wardrobe of 33 pieces that I will wear over the next 3 months, aka Project 333. I honestly think it’s been in every capsule I’ve done, which is a great indicator of how versatile a chambray shirt really is! All of the other clothing items used to style this shirt are also included in my fall capsule.

I wanted to keep all three looks office appropriate but I tried to add a little fun where I could. I’m a firm believer that we should be able to wear most of our clothes in the majority of situations that we encounter in our daily lives, and not just for certain occurrences.  

Style a Shirt // Look 1 – Business Meeting

I wanted to create a look that was perfect for the office and I think this fits the bill perfectly! For my first attempt to style a shirt for fall, I paired the chambray shirt with a pair of straight leg crop pants and a pair of oxfords. I buttoned the shirt all the way to the top but I left the ankle exposed to allow for a more casual vibe. I could just as easily see a pair of fun socks peeking out when it gets a little colder. 

A woman is standing against a light grey wall. She is wearing a medium blue chambray shirt tucked into a pair of black pants with a black belt around the waist. She is holding a black handbag and is wearing black patent oxfords. Her right hand is in her pocket and her right leg is bend slightly. Her brown hair is left down and it is curly.

I kept the accessories simple with a black leather belt, a classic, structured bag and a beautiful everyday watch. I love the masculine vibe of this outfit with the straight leg pants and the oxfords paired with the feminine elements of the shirt (puffed sleeves, ties, collarless). It’s definitely one of my favorite ways to dress lately.

A closeup of a woman's torso and top part of her legs standing against a light grey wall. You can see her pants, handbag and watch more closely.

Style a Shirt // Look 2 – Brunch

For my second attempt to style a shirt for fall, I’m going in a completely different direction with this outfit, which I think is beautifully feminine. I layered the shirt over a floral print, button front dress that I purchased secondhand over the summer. I left a few of the bottom buttons undone and tied up the front tails of the shirt. I am a huge fan of a tied shirt over a dress and it’s become one of my favorite ways to style a shirt! I think that it shows the versatility of both pieces perfectly. While this outfit would be appropriate for some offices, I also think that this look would be perfect on the weekend. I could see this being the perfect outfit for brunch with friends, a trip to the local market or library, or out for dinner.

A woman standing in front of a light grey wall wearing a medium blue chambray shirt knotted at the waist over a navy dress with tan flowers. She is wearing brown suede boots and has a brown leather bag on her shoulder. Her hand is resting on top of the bag. Her hair is pulled back and a few curls frame her face.

I added a pair of brown suede boots and a brown leather bag as I think they tie in nicely with the tan flowers on the dress. I left a few buttons open at the top of the dress and added a pair of simple gold hoops and my everyday watch. In keeping with the feminine vibe of the outfit, I pulled my hair back into a low bun and let a few pieces fall around my face.

A closeup of a woman wearing a medium blue chambray shirt knotted over a navy dress with tan flowers. You can see her brown handbag more closely.

Style a Shirt // Look 3 – Drinks with the Girls

I knew as soon as I decided that I was going to write this post on how to style a shirt of fall that I had to include these high waisted jeans! They’re a recent secondhand purchase and I’m very excited to get a lot of wear out of them this fall. I love the mix of the chambray with the dark wash denim and how the tighter fit of the pants pairs with the “blousiness” of the shirt. 

A woman standing in front of a light grey wall wearing a medium blue chambray shirt and high waisted dark wash jeans. she is holding a tan straw bag in her right hand and has her left hand placed on her left hip. She is also wearing leopard print mules. Her brown hair is pulled to one side and she is wearing blue earrings.

I wanted to keep the accessories fun. In addition to my everyday watch and a gold necklace, I added a fun straw bag, a pair of leopard mules and a pair of funky blue earrings. I pulled my hair over to the side and secured it with a clip. 

I think this outfit would work well in a casual Friday scenario at the office, if your office does that kind of thing. I could also definitely see this outfit as a great “going out with the girls for drinks” outfit! Can’t you?!?


The most sustainable piece of clothing is the one that you already own. It is my hope with these types of posts that you will feel inspired to think of a variety of ways to wear something that you currently have hanging in your closet. That you’ll feel a new excitement about an old piece.

Did you enjoy this post on how to style a shirt for fall? I’d love to hear what your favorite look was: Sophisticated, Sweet or Sassy?

Until next time,

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This Post Has 8 Comments

  1. Anissa

    I love this! I can even picture this button up in linen 🙂 I don’t have one in my wardrobe, it might be time to get one! I often have simply shirt. This one, by itself, adds value to the look 🙂
    I love your pictures, they are always perfectly taken! The floor is always of the same size in each picture! Any tuto? 🙂

    1. Gillian

      Hi Anissa! Thank you! Yes, I agree that a button up linen shirt would be great styled like this. I recently found a secondhand oversized one at a consignment shop that I am loving!

      I place my camera in the same place to take pictures every time so I think that helps with the consistency 🙂

  2. Mon

    I feel the same about button up shirts – I realised that a deep v-neck suits me best so I will revisit my shirts. The chambray shirt is gorgeous, I love all 3 looks. Have you done any posts about how you do your photography? I’d like to hear about that. Thanks x

    1. Gillian

      Thank you so much for your comment, Monica! Why do button up shirts have to be so difficult haha?!?

      I have not ever done a post about that! I’ve never even though about it, but I will now. Thank you for the suggestion!

  3. Chloe

    Love this! Your style has been inspiring me so much lately!

    1. Gillian

      Thank you so much Chloe! That means so much to me <3

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