I'm Lisa Kirk, a wife, mama, writer, and founder. Since 2010, Something Pretty has been home to my favorite memories, reflections, and inspirations. Thanks so much for reading!

In Search of the Perfect White Button-Down


In a few months, I’m having headshots taken for the new business I’m working on. While trying to plan an outfit that feels the most authentically like my style, I keep coming back to the same look: a relaxed white button-down, classic jeans, and a bright lip. I actually steered clear of white button-down shirts for many years–putting one on always made me feel like I was getting ready for a high school choir concert! Even so, I’ve spent the last decade-plus LOVING the look on other people and filing away tons of white button-down outfit inspiration. Maybe I’ve finally spent enough time out of high school to get back into this classic wardrobe staple, but whatever the reason, I can’t stop thinking about them. Flipping through all that saved inspiration (a handful of which you can take a peek at below), I’ve narrowed my perfect white button-down search down to styles with a boyfriend-esque fit and a soft, lightweight fabric. I think both elements skew the look less high school choir and more effortless chic ;)

Clockwise from top left: @aerin, unknown, Sezane, Sezane via Katie Considers, unknown, Make Life Easier, Elle UK, PopSugar, InStyle

In no particular order, here are my top contenders. I’m considering some that fall at higher pricepoints than what I’d usually spend on a shirt; since this is such a classic piece, I’d be up for investing in one that will still look great a decade from now.

1. Ann Mashburn Boyfriend Shirt ($175)

2. Sezane Tomboy Shirt ($110)

3. Ayr The Deep End Shirt ($135)

4. The Boyfriend Shirt by Rochelle Behrens ($98)

5. Cuyana Poplin Overlay Shirt ($125)

6. Grayson The Hero Button-Up ($148)

7. J. Crew Relaxed-fit crisp cotton poplin shirt ($78)

8. Summersalt The Perfect Boyfriend Shirt ($75)

If you’ve tried any of these, or have another favorite I should know about, I’d love your thoughts!






  1. Teresa says:

    Oooo I love a good white button down, and your inspiration board got me excited for slightly cooler weather in which the thought of wearing anything with sleeves doesn’t seem preposterous! (It’s always this time of summer when I start pining for cooler weather wears).

    I was gifted the Ayr Deep End shirt and I love it so much that I’m putting the oxford blue version on my wish list. It is incredibly comfortable and flattering and holds up super well. However, I would not describe it as made from a soft, lightweight fabric. It’s definitely a bit thicker/heavier/sturdier than other white button downs that I have.

    Can’t wait to see your eventual headshots, which I am sure will be absolutely lovely!

    • Lisa says:

      Haha! Couldn’t agree more about sleeves right now ;) Thank you so much for this insight!! Super helpful. Honestly, I love the cut of the Ayr shirt so much, I might buy one just to try it out and return it if it’s not perfect!


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