I had a lot of fun making my let’s dress like we’re in the Parent Trap post last year – and I knew I needed to follow it up with something just as iconic.
Then I realised: why not pick my favourite film? (C’mon, y’all know what I’m talking about.)
Enter When Harry Met Sally. Even though the film is 30 years old, Sally’s wardrobe is surprisingly pretty on-trend for 2019. Her menswear-inspired closet is bursting with enough blazers, patterned shirts, thick knits and mom jeans to make the sartorially savvy drool.
Sally’s Central Park look
This feels like Sally’s most iconic outfit – although that might just be because this scene is on the DVD cover and poster.
It’s a bold look, inspired by Woody Allen’s Annie Hall (1977), and features an oversized bowler hat, slacks, and clashing prints.
Arguably it’s an outfit only the beautiful Meg Ryan could pull off. I wouldn’t blame you for shying away from slacks and a bowler hat. But it’s definitely a look we could draw inspiration from – whether that’s being braver with our accessories, investing in a thick blazer, or committing to matching our gloves to our handbag.
Sally’s velvet bridesmaid dress
I’m not suggesting emerald-hued velvet will be gracing the wedding aisles anytime soon. (Or am I?)
But I can absolutely see velvet dresses becoming the look du jour of this year’s Christmas parties. Keep the colour, keep the fabric – just update the silhouette. Like these:
Sally’s red sweater outfits
Sally’s red jumper makes two appearances in the film – which is pretty rare for a movie, isn’t it?
First, she teams her scarlet sweater with a black pencil chic. Simple, chic. Later, it reappears beneath a maroon blazer and mom jeans for a stroll about the park. I can see Alice Catherine (one of my favourite bloggers) wearing something similar to this.
Would I personally have swapped out the red jumper for cream? Yes (I want Harry’s jumper, actually). But props to Meg Ryan for pulling off the maroon/red combo.
Sally’s diner outfit from, y’know, that scene
The most famous scene from the movie, where Sally simulates an orgasm just to prove a point. We’ve all been there, right? No?
It took a couple of watches (‘I’ll have what she’s having!’) before I even noticed Sally’s outfit but it’s actually a pretty great one. Mindy Kaling even recreated it (with the help of her own Harry, BJ Novak).
That looks like a real cosy knit, right? I like that she’s dressed it up with a fancy shirt.
Sally’s casual weekend look
Pith helmet aside, this outfit is BACK. IN. STYLE. The high-waisted, belted jeans. The loafers. It’s all so 2019. (This makes me wonder if perms will also come back? I’m not ecstatic about that.)
Sally’s exemplary coat collection
Sally’s collection of oversized coats are quite impressive – and actually, a template for the ideal coat collection.
There’s the hardy, outdoorsy camel-coloured coat. Great for lugging a tree through the streets of New York on your own (or y’know, going for a long walk?). There’s the fancy, dark coloured, wrap-around coat which you can wear on terrible dates. And then there’s the neutral every-day coat which you can throw on over anything. Particularly handy for picking out trees with your best friend.
And that’s how to bring a bit of Sally Albright into your wardrobe! So, which film/character should I do next?
Image credits: Columbia Pictures/Everett Collection
