How to Rock a Button-Down Without Really (Appearing to Be) Trying

I’m a sucker for a good button-down. (I recently discovered the joys of wearing menswear tops, but I love them all indiscriminately!). “But wait” you might say, “button-down shirts are so basic! Aren’t they just boring?” Au contraire. In my opinion, collared shirts are highly underrated by the general public. They can have the ability to make an outfit look put-together and classy while also exuding a cool-without-even-trying kind of vibe à la Caroline de Maigret. Ironically, though, the “effortless” aura of a button-down is best portrayed when the styling receives a bit forethought. Here are three of my favorite tips for styling a button-down that ups the ante of this wardrobe basic into a cool-girl star.

1) Starting simple: how much to (un)button?

Answer: just enough to show a hint of skin. “Hint” is the key word here: buttoned up all the way up to your neck can make the outfit appears stiff, unless it’s done with purpose; but undo too many buttons, and the ensemble can lose its mystique. It’s up to you to play around with how you balance it and what you’re comfortable with. If the button placements don’t quite fall where I’d like (i.e., one more button down and the look gets a little too ~exciting~ for my taste, but one more button up and the shirt doesn’t lay quite right), I like to go one button down and then layer a lacy bandeau underneath in a neutral color (black or skin-toned) to add some extra coverage.

2) Cuff it up

I always, always cuff the sleeves of my button-downs. It really adds an easy-undone look to the ensemble that exudes a certain effortlessness. Here’s my favorite way to cuff my shirt sleeves to add a bit of casual “I-didn’t-try-but-still-look-great” :

1. Flip over the hem of the sleeve and pull it to your upper arm


2. Fold up the bottom portion of the sleeve, so that some of the upper hem remains visible (about 1/2 – 3/4 of the way up)


3. Adjust the ends by pulling and tugging the edges until the cuff lays slightly less “flat”


Voilà! Perfectly imperfect sleeves.


3) Tie the knot

We finish with my absolute favorite button-down styling trick, which is simply to tie the ends in a bow. To do this, begin by doing up almost all of the buttons down to about where the shirt hits your belt or a little above (you should have one or two buttons that remain undone at the bottom). Then, take the two “tails” of the shirt and just tie them in a small double-knot!

OUTFIT DETAILS – Top: Hinge; Shorts: Madewell

I love this trick because it has a dual effect: First, it adds an unexpected flair to a normally basic garment, which immediately takes the outfit from “standard” (boring) to “interesting” (good!). Second, the bow highlights the waistline, which creates a flattering hourglass-shaped line. This style works particularly well when the top is worn with high-waisted bottoms, because this allows you to tie it off higher up and closer to your actual waist. It also has the added bonus of allowing you to wear a shirt that might be larger than your usual size (such as a men’s shirt) without it looking too long or totally hiding your figure.

So that’s it! 3 ways to instantly up the game of your basic button-down. Go forth and rock the “cool without trying” button-down look.

– jennifer

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