Here Are The Exact Pieces You Need To Dress Like Sally Albright This Fall
7 perfect looks for high-maintenance women who think they’re low maintenance
Image: Castle Rock Entertainment
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by The Candidly Team
Every delicious bit of dialogue from When Harry Met Sally lives agelessly in our brains. Thanks to the brilliance of writer Nora Ephron.
Of course something else that lives on agelessly in our brains are Sally Albright’s clothes. And that is thanks to the brilliance of costume designer Gloria Gresham. (Fun fact: she was also an assistant costume designer on Annie Hall.)
Every September we start to think about those clothes, that tomboyishly chic spin on classic, late 80s/early 90s autumn-in-New-York style. Is it not how we all want to dress in the fall?
We already copied her perfectly mismatched bedroom ages ago, but we finally decided to do a real, obsessive hunt for all of Sally’s clothes: pieces we know we’ll love (and will last) forever because we’ve already loved them for 37 years (which by the way is five years older than Sally was was when she sobbed about turning 40 … “in eight years.”)
But rather than be existential like Harry about all that, we decided to be pragmatic like Sally and lay out all the clothes we’ll be buying to finally live out our sartorial dreams, because when you realize you want to spend the rest of your life dressing more like Sally Albright, you want the rest of your life to start as soon as possible.
Images: Castle Rock Entertainment
1. The Red Sweater And Mini Skirt
The red sweater is obviously iconic but note the length. THAT, my friends, is what separates it from all other chunky cableknit sweaters*. The length is cute, feminine, waist-nipping, and paired with a shortish skirt* and a good pair of unrippable tights* your legs looks longer whether you’re in flat boots or loafers or ballet flats.
2. The Oversized Turtlenecks
If you wear one of these tucked into a pair of jeans instead of a t-shirt or a basic long-sleeve, you will appear 71% more styled. And as women who “get cold when it's 71 degrees out,” we will never not appreciate a cocooning turtleneck.
Images: Castle Rock Entertainment
3. The Brown Blazer And Relaxed Jeans
We obviously love layers and fall clothes, but we admit, when done wrong, they can look boxy and boring. Look at this silhouette! Sally made us last after three important things with this look: a tailored, non-black blazer* that defines our waist, a cozy, but fitted turtle*, and the crossbody bag*. The strap makes it part of the outfit and adds even more definition. So simple yet so smart.
Image: Castle Rock Entertainment
4. The Iconic Fall Fit
No one has made us lust after a blouse and drapey trouser than Sally Albright (with the exception of maybe the “low-maintenance” Ingrid Bergman). Brown and white polka dots were clearly a thing that year because just months later Pretty Woman came out with THIS dress. But we get it, because polka dots are understated while still being interesting. Plus, we can be feeling bloated and blah inside our bodies and throw on this outfit and suddenly feel covered up yet put together, then add the hat and life is better and more autumnal and simply designed for strolling with a friend in the park.
Image: Castle Rock Entertainment
5. The Only Way We’re Wearing Shorts From Now On
This outfit might be the divisive, wagon-wheel coffee table of this article. We’re the first to admit we have a complicated relationship with shorts. But we feel differently about the trouser short*. With an oversized, striped blazer and a classic button-down, it’s chic but actually accessible, enticing, and delightful all at once - much like Meg Ryan herself.
Image: Castle Rock Entertainment
6. THE CHUNKY, CROPPED SWEATER
Again, this length is going to make every skirt, every relaxed pair of jeans, and every high-waisted trouser look better on you. The silhouette is just more flattering/youthful and never frumpy. And since we basically live like Sally in cold weather, wearing sweaters as tops, we buy them in multiple colors in real cashmeres and cottons that last but don’t cost a fortune.
Image: Castle Rock Entertainment
7. The Little Black (And Little Pink) Dress
It is taking everything in our power not to just caption this section “BABY FISH MOUTH” and leave it at that. But in all of Sally’s (likely meticulously organized) closet of sweaters and blazers and pleated pants and long shorts and knee socks and tights, how absolutely alluring and adorable were her curve-complementing dresses that we still want today?
BONUS: THE ACCESSORIES
Sally made us lust after sensible things like bowler hats and glasses chains. But she also had lustrous things like sweeping waves and crimped curls and the most illuminating peach lip gloss on this earth*. Needless to say, something would have been missing had we not found all of that as well.
The Hats*: We feel in our hearts that the Sally of today would have found her hats at Gigi Pip, but if you must have that vintage, 90s bowler from J.Crew go HERE*.
The Chic Readers Chain*: "Someone is staring at you in personal growth."
The Blowout Spray*: Sally’s waves were surely compliments of Aqua Net*. But THIS* is the spray that keeps our curls looking bouncy, soft, and natural.
The Glossy Peach Lip*: This gloss makes our lips look succulent and full without being sticky. A bit of magic really.
The Days-of-the Week Underpants: Someone pleeeease put this pack in our Christmas stocking. They even have Sunday!
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