I Love Your Style: Annie Hall

Who or what inspires your style? Many of us use musicians (like Debbie Harry) or movie characters (like Elvira Hancock) as style inspiration, even though, most of the time, they are being dressed from head to toe by the best stylists. Which we don’t have. And sometimes it’s damn near impossible to work their Hollywood looks into our not-so-Hollywood lives. I’ve made it my mission to tap into the mind of a fashion stylist and show you how to take your style inspiration – whatever it may be – and make it more you!

I’m probably not the first person to break the news to you that Annie Hall and (500) Days of Summer are essentially the same movie. (And if I am, I’m sorry.) Diane Keaton and Zooey Deschanel play basically the same character and each movie illustrates love, going back through time to figure out what (or who) went wrong with back and forth over-analyzing.  But to me, the most important aspect of these movies (besides the “groundbreaking” lessons I learned) is they both demonstrate the iconic style of the fashionably quirky female protagonists.

In Annie Hall, Annie and Alvy attempt a relationship.  They break up.  They get back together.  The process repeats, blah blah blah.  It was a great movie no doubt, but half the time I was watching, I was more focused on how I can dress like a women trying to dress like a man without looking like a man.  Does that make sense? Let’s hope so.

For those of you who don’t know, Annie Hall’s style was revolutionary for its time. Before this movie, it wasn’t extremely popular for women to be rockin’ a tie, vest and high-waisted, wide-legged khakis without getting “WTF are you thinking?” looks from their peers. Annie Hall pushed the envelope, blurring the lines between male and female style, forever changing the landscape of women’s fashion. There’s a difference between something a man would wear and menswear, and the character of Annie Hall proved that. Katherine Hepburn may have started the “pants-on-women” trend, but Annie took it to a whole new, somewhat crazy, level. And it worked, because it was classic and bold at the same time.

The menswear style is a female approach to a masculine type of piece; a classic watch, a vest, fedoras and suspenders. It’s adding just a touch of maleness to the shape, cut and silhouette of traditionally female style.  It’s sexy and chic, modern and classic, structured yet relaxed. It’s no surprise that this is a trend that’s been around for decades, all thanks to Annie.

Wanna try it out? Don’t worry, you don’t have to go quite as balls to the wall at Ms. Hall (her hats were always a bit over the top). Just choose a few dude-inspired pieces and go from there.

Watch, Skirt, Shoes, Suspenders, Shirt

This outfit uses Annie’s love of menswear yet feminizes it to be a little more wearable while still iconically recognizable.  The high-waisted khaki skirt plays off of the khaki pants Annie is famous for, but which most 21st-century women wouldn’t be caught dead in. (Pleats? Ew.) Instead of going for a structured vest and tie (both of which are totally doable – don’t be afraid to try ’em out!), I opted for suspenders to add the masculine twist.

The white shirt and oversized watch are classic pieces every women should have in her closet, no matter what style you lean towards.  And the shoes are played off of the oxford style flats that would be most appropriate for this outfit, but won’t freak too many people out by the dudeliness of them.  If you’re bold enough, wear the most masculine shoes you can find (in the women’s section, that is!)  and rock this outfit like you pioneered it yourself.

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