The world met Harry and Sally in 1989 to the sounds of Harry Connick Jr in Central Park. With her always perfect blowouts and dangerously provocative loafers, Sally Albright’s Type A Style Guidelines have some rules that defy the test of time and the definition of sexiness.
Rule #1: There is no such thing as too much face powder or mascara.
While I think even Tracy Turnblad would condemn her hairspraying habits, Sally’s makeup routine is quite admirable. Unfussy foundation, rosy blush, and loads of powder leave her looking like a porcelain doll even when she ugly cries, and as she ages throughout the film, her eye makeup becomes more sophisticated and feminine. A simple line of top liner and about three coats of volumizing mascara is all she needs to make her neurotic tendencies look borderline cute.
Rule #2: Grandpa Sweaters are sexy.
I first watched When Harry Met Sally when I was sixteen years old, and I have been trying to build a sweater arsenal to match Meg Ryan’s ever since. Tucked into the world’s first mom jeans, Sally’s sweaters are the epitome of ugly chic, and their muted colors and rich textures look so cool against the backdrop of Manhattan.
Rule #3: Masculine details are underrated.
Wide belts, penny loafers, and Bermuda shorts should not be shunned to the clearance section of Brooks Brothers. They can be incorporated into a woman’s wardrobe with ease, and it’s a subtle to way to show dominance against men who feel the need to express every feeling they have every moment they have it.
Rule #4: You don’t need a reason to dress up.
My favorite thing about Sally is not that she embraces masculine style, but that she knows how to look like an old school princess when the time is right. My favorite look in the movie is the little scalloped pink dress she wears to play Pictionary in her friend’s living room, and no one bats an eye to the fact that she isn’t in a pair of trousers. On New Year’s Eve, she looks like an absolute Barbie Doll, just by putting on the right shade of pink lipstick and silver necklace.
When a woman is comfortable with her sexuality and her dating habits, she has no problem being high maintenance and thinking she is low maintenance, and dressing to please only her.