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5 Ways to Channel a Modern Annie Hall, According to Leandra Medine

Because nothing is more appealing than masculine silhouettes on a woman.
5 Ways to Channel a Modern Annie Hall, According to Leandra Medine Because nothing is more appealing than masculine silhouettes on a woman.

Sometimes, a girl’s got to do what a girl’s got to do, and that’s to walk out of the house looking as if she just raided her father’s closet. At one point in your childhood, you probably picked office wear as the theme for a dress-up sesh in which you strategically paired dad’s candy-striped silk tie with mom’s red leather 3-inch pumps. But as you grew older, you realized that there is room for that sort of outfit in the real world, all thanks to the style inspiration served up by Diane Keaton in Woody Allen’s Annie Hall. 

For this week’s blogger #OOTD roundup, we turn to the Man-Repeller Leandra Medine-Cohen, who is known for her modern day take on Annie’s iconic look, for some notes on how you can channel borrowed-from-the-boys with an updated twist. Let’s begin.

TIP #1: Tailored pieces in pale neutrals are your best friend.


Substituting khaki for alabaster is one quick way to instantly modernize Annie’s color palette but remember, nailing this look is all about the fit and the tailored details. Don’t go for jackets that are too snug or too loose. 

TIP #2: Stick to a minimal color palette.

Annie is very safe with her color choices, which essentially makes things easy to mix and match. You can pair pieces together that are two to three shades lighter to break up the monotony.

TIP #3: Mind your proportions.

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It’s easy to look like you're drowning when layering pieces, especially if they don’t exactly cling to the contours of your body. To avoid becoming a walking pile of men’s clothing, simply mind the proportions of the pieces and study where they cut you off. Take a pair of high-waisted wide leg trousers that immediately shortens your torso, simply offset it by wearing a longer jacket that hits right at the middle of buttocks.

TIP #4: Take from day to evening by adding a super girly piece.

So let’s say you’re wearing wide pinstriped trousers with a long-sleeved pussy bow top. Way too conservative if you’re planning to go drinking after work, yes? How do you transition without doing a full outfit change? Switch the top with something that shows a bit more skin like a sequined slip. Easy!

TIP #5: Feel free to think that you’re Hugh Hefner. 


By this we mean embracing the concept of pajama dressing. Silk trousers paired with a tie-around coat that has a wide and manly lapel can still look very Annie by parking it with brogue loafers.

Images from @manrepeller and @leandramedine.

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