How to Style a Button‐Down Like a Pro

Chic, timeless, and totally effortless—a wardrobe staple. Let's style it!

Author

Angela Howenstein
August 28, 2025

I’m not kidding… I blinked and suddenly it’s late August. How?? Summer’s basically in the rearview and I don’t know if I’m quite ready for the change!

No matter WHAT season it is, my one go-to is……

The button down shirt. Yep!

The reason I love a good button down is because it’s super versatile and always flattering. It’s a GREAT basic too, that anyone can wear. I’m styling my go-to’s in a few different ways to give you a little inspo. Happy reading!

My Favorite Button‑Downs That I Wear Like It’s My Job

When I find a great button down, it gets so much wear. I’ve been living in my J.McLaughlin, H&M and Z Supply shirts all summer and as we head into Fall, I’ll be wearing them, but in different ways.  You all know that I’m not brand-conscious and I do love a bargain, so most of my button-downs are in a variety of price ranges.  

Stripe Oversized Button‑Down
So…slightly oversized with a drop shoulder—for that relaxed, lived‑in chic. Super on-trend right now but also so flattering when you pair it with something slim on the bottom - think straight jeans, a skirt, shorts  or tied over a dress. I love THIS ONE and THIS ONE.

  • The “Go‑To” White Staple
    Here’s the thing…a white button down comes in a variety of shapes and fabrics for all different occasions.  I’m wearing cotton or linen (even if it’s wrinkled) with denim shorts (see video) for a casual feel or a nice stretch cotton blend when I need to look a little more pulled together.  For a slim fit, I like THIS ONE  If you like a little ruffle collar, try THIS ONE.

  • Gauzy Lightweight Beauty (<$40!)
    100% cotton, breezy, relaxed fit and SOOOO chic. My first choice on this is white, but that’s only because that’s kinda my uniform :)  I have THIS ONE but these are a great price HERE and HERE.

  • Linen Button‑Down (Under $50)
    Linen isn’t always EASY.  Some people can NOT handle the wrinkles while others WANT the wrinkled look to compliment their easy, breezy personal style. If the “lived in” look is for you, then linen is your BFF. Found this awesome NAVY BLUE as well as a classic white HERE.

  • Classic Cotton Option (Investments)
    I happen to LOVE a fitted, cotton option whether I tuck it in or leave it hanging out.  It’s all in personal preference and the cut of the shirt. This STRIPED ONE is great and I love the sleeves on THIS ONE.

Here are a few ways I am styling my fav denim shorts as well as some great transitional button downs that will be great for fall!

My Go‑To Tips for Styling Button‑Downs

There are zero hard fashion rules when it comes to button down shirts. But, I do have a few tips that might help you style your fav just right. Check out how ladies on the street are styling THEIR button downs below.)

  1. Proportion
    If you’re wearing an oversized top, consider wearing something more slim on the bottom. On the other hand, if the button down is more slim, this is your chance to wear wide legs jeans or a pleated trouser. Try THIS CUTE ONE for a flattering oversized look or THIS or THIS.

  2. Layer!!
    As we head into Fall, layering is your BFF.  If you’re going to put on a button down, think about wearing a tank top underneath and leave the button down open and hanging out - kinda like it’s a jacket. (I did that HERE).  When you are wearing it as a more tailored look, then pop a sweater over your shoulders or put it on right over the shirt - easy.  For a very polished look, a button down under a blazer is just perfection because if you take the jacket off, you’re wearing a great top that is office-appropriate and just plain great looking. (If you are part of the ‘over-heaters anonymous club, THIS BLAZER COMBO is for YOU). Love this OLD SCHOOL one and THIS for fun.  Layer with a great SWEATER or a great BLAZER.


     

  3. Max Out the Accessories
    I’m famous for a popped collar. Yep!  As long as the collar is not too big, I pop it right up and wear my hair back in THIS BARRETTE (I have an old one from Anthro).

    I also like a collar that lays kinda flat like THIS - that’s SUPER flattering and a bit of a more “sexy” look.

    Wearing a button down is a GREAT time to put on that jewelry! I love a CHUNKY BEAD NECKLACE or a dainty AFFORDABLE CHAIN or this FANCY ONE (obsessed)  when I’m super casual. 


    I don’t often wear big earrings with a button down because they kinda just get in the way :) I prefer something like THESE or THESE (old school).

    Y’all know my other famous look is to ROLL THE SLEEVES!  I don’t mean a proper folded roll, I mean a messy slouchy roll above my elbows.  Did you know that rolling sleeves that high will give the illusion that you’re taller than you are? Yep, it’s true!  When you’re all rolled up, throw on a STACK OF BRACELETS (I own this) - super chic.  You can just do SO much with hair and jewelry to give the same ole shirt a different look each time.

Outfit Ideas You Need in Your Life

Facts & Rule of Thumb

Fact: Button‑downs are your wardrobe savior. Dressy or casual, they go wherever you need ’em and they go with just about anything in your closet.  They can be in any price range and be fab. Button downs are endlessly stylish, and incredibly versatile….that’s why they are my #1 uniform basic :)

Rule of Thumb: You can go for the oversized or tailored look - just make sure you balance it out with what you are wearing on the bottom.. Tuck, layer, and accessorize to make this wardrobe staple look like the everyday chic gal that you are :)

Let’s make this an important part of your Fall look, ok?

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