Fall 2019 Wardrobe Inspiration: When Harry Met Sally

When Harry Met Sally is a fan-favourite rom-com that’s arguably hailed as one of the best. It turned 30 this year, and not only does its plot remain a timeless dating troupe across generations, its characters’ wardrobes remain incredibly stylish.

I’ve reimagined Sally’s best looks below to serve up some fall wardrobe inspiration.

The Corduroy Skirt

When Sally helps Harry unroll a carpet at his new apartment, she does so wearing the chicest mid-thigh skirt. Harry compliments her by saying she should wear skirts more often, and we couldn’t agree more.

The zipper cuts diagonally across my corduroy skirt to give it a modern update and bring it out of the eighties. I then paired it with a green cable knit to combine the best of two fall staples into one outfit.

The Chunky Cable Knit

This versatile piece is too good on its own to not have a separate mention. You can wear it with the corduroy skirt above or high-waisted jeans below. While Sally wears one in multiple scenes throughout the film, we have to tip our hats to Harry for his timeless take on the chunky cable knit. In the same scene above, Harry sports his with dad runners and trusty jeans.

This time, I’ve channeled Harry below—I’m just missing a carpet to roll out.

The High-waisted Mom Jeans

These jeans are perfect when you want a pair that’s tapered but gives you room to enjoy a big brunch. The cinched waist elongates legs and keeps everything tucked in, and their stiff fit is a sign of true denim. Sally wears hers during the two’s spontaneous karaoke session at the electronics store.

Like Sally, I’m wearing mine with a turtleneck.

The Menswear-inspired Blazer

It’s loose and broad-shouldered. It was a NYFW fashion takeaway, and it goes with everything—from high-waisted jeans to a paperboy cap. Sally’s men’s blazer is worn multiple times throughout the film. Not only does she wear one during their central park stroll, we see her don a grey checked version on her way through the airport.

I’ve paired mine with jeans and flats—ready for a stroll through the 6ix.

The High-collared Blouse and Cardigan

The famous scene at Katz’s Delicatessen should be noted for more than a woman’s ability to fake an orgasm: Sally’s outfit is iconic. Here, she wears a white collared blouse underneath a chunky cardigan, giving her effortlessly cool vibes as she makes an important point to Harry. The transitional temperature makes this top ensemble the perfect choice. It keeps your neck warm without needing any additional accessories.

Incorporating Sally’s looks into your wardrobe is easier than you think. You probably already have similar clothes hiding in your closet—you may have just forgotten where they are. Luxury consignment Canada Designer Swap’s closet concierge services includes closet organization, so you can let your wardrobe inspire you all over again.

What movies inspire your fall wardrobe choices? Let us know in the comments!

Designer Swap is Canada’s online luxury consignment shop and Toronto-based fashion blog. Find gently-used and pre-loved authentic designer pieces to purchase and read about the newest fashion, beauty, and lifestyle trends. Make sure to check us out on Instagram and Facebook!

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Images courtesy: reshot.com, Jacqueline Gubiani