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How I Learned to Love the Button Down

How I Learned to Love the Button Down

The buttondown shirt is a classic addition to any wardrobe. It's come a long way since its origins in white collar workwear and mass-produced uniforms, and in particular as women began adopting it during the 20th century, it has evolved from a symbol of rigid conformity into a fashion mainstay that is as versatile as it is timeless.  

However, all throughout my adult life I’ve struggled with embracing this wardrobe staple. I could never find one that fit comfortably, and rarely liked how they looked on me. Many shirts came and went, with most of them being donated until finally, I swore them off forever.

And then last year, I saw her: Ani Bezzerides, the pint-sized, hard- as-nails cop from the second season of True Detective who has an I don’t care I’ve got sh*t to do sense of style, carried off with such ease that she oozed sex appeal. It’s the nonchalance with which Bezzerides so effortlessly rocks the relaxed shirt – unbuttoned just so – that inspired my search to find one just like it.

After several months of searching, I found The One – so soft in its drape with an almost suede-like touch to it, and in just the right shade of dark blue. But best of all, it opened my eyes to what I'd been doing wrong my entire life: I'd been wearing shirts that were too tight.  

Ironically, by going for the “fitted shirt” look, I always ended up with one that didn't fit at all; the hem would ride up, the buttons would strain, and the shoulders would twist awkwardly. In my obsessive quest for the perfect shirt, I realized I needed to loosen up, literally. By going a size or two bigger, I found the kind of fit I didn't know existed: relaxed enough that I can wear it layered over a tank Bezzerides-style, but flattering enough that I can pair it with a leather skirt to dinner, the delicate lace of my undergarments peeking out juuust enough to keep it classy.

This simple adjustment was so revolutionary that I began applying this approach to the rest of my wardrobe. I started buying medium-sized t-shirts from the men’s section – they fit better, they feel better, and they last longer. For the last three dresses I bought, I have opted for a size or two bigger. Just last month I found an amazing oversized floral printed shirt at Goodwill. I wear it as a kimono, unbuttoned over slouchy pants (with an elasticated waistband; another way I've embraced a more flexible fit).

 Somehow, by deconstructing a traditionally utilitarian, masculine piece of clothing, I unwittingly discovered for myself a new sense of femininity. My new philosophy around fit is the perfect sartorial embodiment of leaving something to the imagination, but it's also revealed an unexpected benefit that goes way beyond how I am on the outside.

Not only am I more comfortable physically when my clothes are looser, I am more comfortable psychologically. I feel sexier, more confident, more put together, more grown up. My weight rarely fluctuates, but it does change how it's distributed around my body, so I sometimes find my waistband is a little looser or a little tighter than normal.

 Now, there is no ‘normal’ anymore; instead of me fitting into my clothes, they fit around me. Instead of clothes clinging co-dependently to my body, we move together in harmony; it creates a sense of negative space between the fabric and my skin that’s almost intimate.

That physical gap represents a freedom that nobody else can see; a space that's all my own to do with what I choose. There's a feeling of safety that I get from being cocooned in fabric that gives me room to move, to grow, to change; I'll always be accepted by these clothes for who I am at any particular time. It's unconditional, and as a result, the relationship between my clothes and my body feels healthier, and more lasting. It finally feels like I’m dressing for me, and for nobody else.

The Girl Next Door: A Crossdresser Explains her Wardrobe

The Girl Next Door: A Crossdresser Explains her Wardrobe