6 Fall Outfits I’m Stealing From ‘When Harry Met Sally’

I love any and all Meg Ryan/Nora Ephron joint ventures as much as the next sane person, but When Harry Met Sally is my absolute favorite. I have watched it no less than 12 times, the twelfth being when I recently learned that my boyfriend had never seen it before and I sought to correct that immediately.

Ten minutes into the movie, I realized I wasn’t really paying attention to the plot. I didn’t need to — I could recite the movie start to finish. I was, however, paying extremely close attention to Meg Ryan’s outfits. I’ve admired them before, obviously, but during this particular viewing session they were all I could think about, perhaps because When Harry Met Sally is a goddamn beautiful onion with endless layers to unpack, or perhaps because fall weather is around the corner and Meg’s outfits are autumnal style porn.

Below are six I plan to copy as soon as the tree outside my window turns orange:

Knee socks, khaki Bermuda shorts, a button down and a cardigan is pretty much the perfect outfit for transitional temperatures. My evidence for this assertion stems from the fact that my knees are the only part of my body that don’t seem to freak out when confronted with a chilly breeze. My arms and cheeks and inner thighs and toes, on the other hand, are wimps.

A gray plaid blazer is a fall staple I have yet to acquire, but rest assured it is now at the top of my list. I am also planning to button all buttons right up to my throat, which I will wrap like a gift to the world with a silky scarf. I’m on the fence about mauve nail polish, but let’s touch base again in November.

My mother recently gave me a pair of stiff, dark blue Levi’s that she wore in the ’80s. They reach all the way to my diaphragm and make me look like a bird watcher and I love them with all my heart but until now haven’t been able to figure out what to wear with them. Lo and behold, the answer is simpler than a piece of apple pie a la mode, heated, with strawberry ice cream on the side (that’s a When Harry Met Sally reference for all my fellow freaks out there): a thick white turtleneck and a brown belt.

Just when I was about to relinquish ankle boots to the trend graveyard, this outfit swooped in and re-calibrated my imagination. I’m going to be tucking them under my mom jeans right and left, just you wait. Also, I think I need a messenger bag? TBD.

I love this outfit because Sally wears it in the scene immediately after Harry tells her, “I think you should wear skirts more. You look really good in skirts.” AND SHE DOES. She also proves again and again that you don’t have to overcomplicate an outfit (a definite tendency of mine) for it to resonate. I’m stowing “black mini skirt and cozy red sweater” in the back pocket of my brain as a chic, easy ensemble option for days this fall when I have no idea what to wear but really want to look like a Jil Sander ad.

Last but not least, this outfit inspired the very important revelation that bowler hats are the fall equivalent of bucket hats and I am planning to incorporate one into my wardrobe posthaste.

Now it’s your turn: Do you have a favorite movie or TV show with ample style fodder? I’ve got winter covered thanks to Love Story, but I’m in the market for spring and summer inspiration.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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