My personal style has always tended toward the somewhat tomboyish, and throughout the years, my wardrobe has been punctuated by very specific workhorses. There was the plaid surfer hoodie during high school and the wool herringbone blazer during law school ... and there may or may not have been a bowling shirt phase. Currently, no matter what time of year it happens to be, or what kind of weather I find myself in, or where in the world I might be, your chances of finding me in my J.Crew men's chambray work shirt are excellent. That broken-in shade of light blue that my shirt has attained — and only gets better with age — has become the defining hue of my wardrobe. I'm officially obsessed. My love affair with chambray actually began with a boyfriend's perfectly broken-in shirt, but after losing my borrowing privileges after wearing it a bit too much, I was forced to purchase my own. I knew I wanted a men's shirt with its boxy shape, too-big neck, and too-long sleeves — no formfitting darts or fun details, thanks very much — and I actually went up a size to achieve that perfect, floaty fit. Brand new, the shirt was a good deal darker and not as soft as the shirt I was trying to replace in my heart, so I had my work cut out for me ... which definitely turned out to be a non-issue. At this point, the only way I haven't managed to wear my shirt is with a business suit (but now that you've got me thinking about it ... ) and because it is magically resistant to much wrinkling, it has become one of my most essential travel staples. Snowing in Boston? Throw on a camel sweater and navy peacoat. Driving down the California coast? Just add white jeans and driving mocs. It's been tucked into skirts, belted over sundresses, hung out of my jeans and tied over countless bikinis. I've slept in it more than a few times. It's a daily struggle to make sure I don't wear the damned thing all the time. It's actually pretty hard for me to put into words how this shirt became so important to me. It's not like I wear it because it is a memento like my boyfriend's shirt. The shirt is mine and mine alone. Perhaps it's precisely because we've been through that journey from brand-new to broken-in, together. Perhaps it's because I love how its rugged, old-fashioned aesthetic looks on a woman, or how well it works when juxtaposed with traditionally more feminine pieces. Maybe it's because it makes me feel a little like Cool Hand Luke. Whatever it is, it just always feels right.