WWD’s 2024 Ralph Lauren preview reaches back to Diane Keaton in the 1977 film Annie Hall, describing slouchy khakis, vests and ties as part of Lauren’s menswear story. AFI dates the release to April 20, 1977. AnOther makes the wardrobe more complicated: Ruth Morley was the costume designer, Keaton’s dress was her own vision, and Morley’s daughter said very little Ralph Lauren clothing appeared in the film. That distinction is the point, not a footnote. Diane Keaton style is not a costume recipe. It is a way of making familiar clothes sound like one person’s answer.

Keaton described taking cues from cool-looking women on New York streets, with Annie’s khaki pants, vests and tie coming from that mix. I like that account because it leaves room for taste and accident. The clothes were not a strict matching suit, but pieces talking across proportion, texture and mood. WWD’s later portrait of her collection quotes her sister describing a singular point of view. That is what I am chasing here, not a screen-perfect duplicate.

For this first pass, I would build from a long black trouser. The Jones Wide Leg Pant has a clean waistband and sweep; the Twill Slash Pant gives that black line a softer twill texture, while the Chelsy Wide Leg Pant brings dark pinstripes into focus. Landry Pleated Wide-Leg Trousers add heather gray and front pleats, so the tailoring does not read like one copied uniform. I would put a crisp white shirt above the simpler black shapes, then tuck a pinewood turtleneck into the pleated pair as the weather turns.

One useful check is inseam against the shoes you expect to wear: long hems should skim the top, not gather under a loafer. The Aliza Wide Leg Pants list a 29.5-inch inseam and 27.5-inch leg opening, useful measurements to compare before choosing the rest.

Cotton poplin does quiet work here: it sharpens a wide trouser without turning the outfit into an office uniform. Keaton’s own account points back to New York women she admired, so I would keep the shirt choice personal instead of searching for an exact screen replica. The Next Ex Shirt brings a white-and-green stripe, the Coastal Poplin Oversized Shirt stays bright white, and the Dani Button Down adds sepia stripes to the mix.

The New Shirting Gabe Oversized Shirt gives the same white-shirt idea a little more room, while the Slim Long Sleeve Cashmere Turtleneck shifts the palette to pinewood. For a closer fit, the Abby Cotton Turtleneck Top is white and the Tati Turtleneck Top is black ribbed jersey. Theory’s Turtleneck Sweater, in new ivory wool, is the soft-looking counterpoint I would use beneath a blazer.

I would pair an oversized button-down with a straighter trouser, then let one cuff fall open over a watch or bracelet. Before choosing a shirt, I would check the shoulder seam and sleeve length, then button it at the collar to see whether the neckline still looks comfortable with a turtleneck underneath. The cotton shirts here are non-stretch, so I would pay attention to room across the back rather than relying on the oversized label alone.

What I would skip: two oversized layers on a day when I want a clear shoulder line. Keep the shirt loose or the outer layer roomy, not both, and the outfit keeps its easy, unforced shape.

A blazer is where the film-credit story gets useful. AnOther identifies Ruth Morley as costume designer and records the distinction between Ralph Lauren’s credit and the small amount of Lauren clothing Morley’s daughter said was used. I would rather borrow the idea of a mixed wardrobe than credit every checked jacket to one label.

The Double Take Blazer is the sharp black option, with an asymmetrical collar and padded shoulders. The Madison Avenue Blazer adds a removable dickie and cuffs for a layered effect, while the navy Miller Dickey Jacket keeps its double-breasted front and peaked lapels more traditional. Acne Studios’ Wool Blend Blazer mixes brown checks with a striped poplin underlay, and the Oversized Double Breasted Blazer gives plaid a looser outline.

For a sleeveless layer, the Leo Linen Mix Waistcoat has an adjustable back belt, the Alia Waistcoat brings black velveteen, and the Dakota Linen Vest is a clean ivory linen option. I would wear one of these over a crisp shirt with long trousers, leaving the buttons visible rather than hiding the whole front under a scarf.

At a fitting-room mirror, I would check the shoulder seam with arms relaxed and again with the jacket buttoned. For a waistcoat, look at where the last button lands against the trouser rise and whether the back belt can sit flat. What I would skip: stacking a strong shoulder, a bulky dickie and a high neck all at once when I want the vest to be the detail that reads first.

AnOther recalls Keaton saying she borrowed the hat idea from Aurore Clément, while the wider Annie Hall look also drew on New York women around her. WWD’s 2026 account of Keaton’s wardrobe quotes her sister describing a singular point of view. I read that as a reason to choose one clear accessory, not to pile every reference into the same outfit.

The Wool Bowler Hat is the compact option, with a rounded crown and curved brim. Jude Hat and Harper Panama Straw Hat both have 3.5-inch brims, though one is natural straw and the other Catalina sand. The Dakota Fedora is espresso wool felt with a 2.75-inch brim, while the Field Gardenia Straw Hat adds a chin strap and 3.25-inch brim. For the quieter finish, the 30mm Calf Leather Belt is fig with a gold-tone buckle; the Leo Suede Belt brings chocolate suede, and the Lecce Belt has a self-tie closure.

I would let a bowler sit with a plain black coat and use a broad straw hat when the rest of the outfit is spare. Before choosing, compare brim width with coat lapels and check that a belt’s buckle does not compete with a patterned trouser. The listed dimensions make that a practical decision, not guesswork.

What I would skip: a dramatic brim and busy plaid together on a gray commute. I would let one silhouette do the talking, then use the belt as the small echo.

Keaton’s own vision is the useful thread here: I would borrow the proportion and then choose shoes for the day ahead, rather than rebuild a film costume. The Whitney Weejuns Loafers pair cognac leather with an apron stitch, while the Lexi Suede Loafers keep the penny-loafer idea in a softer upper. The Lana Loafers add tassels and a ruched moc toe; the Classic Ruched Leather Loafers keep the profile black and simple.

For colder mornings, the Ledy Leather Booties have a square toe and a 2.25-inch covered heel. The Brillante Boots are pull-on leather with a low stacked heel, while the Kasey Pull On Boots bring a taller 3.5-inch heel and 1.25-inch platform. The City Gloves add black goatskin and removable rib-knit cuffs, a neat way to bring texture up to the sleeve.

I would wear a penny loafer under a full trouser hem when I want the leg to stay long, then switch to an ankle boot when the hem needs a little lift. My buying test would be to check where the boot shaft meets the hem while standing naturally, and to see whether a glove’s fingertips end cleanly without tugging. For loafers, I would compare the vamp and toe shape to the trouser opening before deciding which proportion looks balanced.

A single accessory can do enough. I would keep the glove cuffs visible with a simple sleeve and leave the rest of the look quiet.

I would choose in this order: trouser line first, shirt or turtleneck second, then one jacket or vest. A hat can finish the thought, but I would not make it compete with a strong plaid or a loud buckle.

The useful part of Annie Hall is not a claim that one designer invented every piece. Morley shaped the costume, Keaton brought her own eye and street references, and Lauren supplied some garments, though the exact amount is disputed. That story leaves plenty of space for the woman getting dressed now.

I would rather see a crisp shirt under a slightly odd waistcoat, with a loafer that makes the trouser hem feel intentional. The best version keeps one small surprise and lets the rest breathe. It should look less like a character study and more like a New York woman who knows her own route.