Style File № 43

How to dress like Annie Hall from Annie Hall

A men's waistcoat over a white shirt, a necktie, wide khaki trousers and a black hat.

Men's WaistcoatNecktie With ShirtWide Khaki TrouserBlack Felt HatOversized Blazer

1977, New York 9 pieces 2 looks

See the pieces
№ 43 Annie Hall The costume the costume designer lost an argument about. AnnieHall Pure Diane Keaton. 1977, New York 9 pieces Men's Waistcoat · Necktie With Shirt · Wide Khaki Trouser

Screenfits earns a commission on some links below, at no cost to you. We choose the garments first and find where to buy them second — never the other way round.

The Wardrobe, Decoded

The costume the costume designer lost an argument about.

Ruth Morley is the credited designer, but the authorship is genuinely disputed. Keaton wore largely her own thrifted menswear; Morley objected on set and Woody Allen overruled her — "Leave her. She's a genius. Let's just leave her alone, let her wear what she wants." Ralph Lauren supplied the tie, vest and shirts, but Lauren himself said "Annie Hall was pure Diane Keaton… she had a style that was all her own." Keaton credited 1970s SoHo street women as "the real costume designers of Annie Hall."

Why we can't let it go

Annie Hall is the only wardrobe on this site where the person wearing it appears to have won an argument with the production. Keaton turned up in her own thrifted menswear, the costume designer objected, and the director sided with the actor.

The result changed how women dress, which is not an exaggeration. Oversized men's tailoring on a woman was not a look before this film and has never really stopped being one since.

And the reason it endures is that it's genuinely comfortable. Wide trousers, a loose shirt, a waistcoat, a hat. Nothing about it is restrictive, which was the entire point in 1977 and is still the point now.

01

The Layers

Anywhere, any weather

Shirt, waistcoat, tie — genuinely men's, and genuinely too big.

01 Men's Waistcoat Buy the men's version. The wrong fit is the whole effect. Budget Splurge
Splurge Price on Amazon Men's Waistcoat Men's Waistcoat Sold on Amazon Budget Price on Amazon Men's Waistcoat Men's Waistcoat Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
02 White Oxford Shirt Loose, long sleeve, button-down or point collar. Budget Splurge
Splurge Price on Amazon White Oxford Shirt White Oxford Shirt Sold on Amazon Budget Price on Amazon White Oxford Shirt White Oxford Shirt Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
03 Silk Necktie Worn loose, knot pulled down. Not a bow, not a scarf. Budget Splurge
Splurge Price on Amazon Silk Necktie Silk Necktie Sold on Amazon Budget Price on Amazon Silk Necktie Silk Necktie Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
04 Wide Khaki Trouser High waist, full leg, pleated. Not jeans and definitely not slim. Budget Splurge
Splurge Price on Amazon Wide Khaki Trouser Wide Khaki Trouser Sold on Amazon Budget Price on Amazon Wide Khaki Trouser Wide Khaki Trouser Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
05 Black Felt Hat Defined brim. It's what makes the outfit read as a decision. Budget Splurge
Splurge Price on Amazon Black Felt Hat Black Felt Hat Sold on Amazon Budget Price on Amazon Black Felt Hat Black Felt Hat Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
In this look 5

pieces · current prices are shown on Amazon

02

Outside

Tennis, the city, a long walk

The same idea in outerwear — everything one size larger than it should be.

01 Oversized Blazer Men's cut, dropped shoulder, worn open. Budget Splurge
Splurge Price on Amazon Oversized Blazer Oversized Blazer Sold on Amazon Budget Price on Amazon Oversized Blazer Oversized Blazer Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
02 Chunky Knit Cardigan Long, loose, earth-toned. Layered over everything. Budget Splurge
Splurge Price on Amazon Chunky Knit Cardigan Chunky Knit Cardigan Sold on Amazon Budget Price on Amazon Chunky Knit Cardigan Chunky Knit Cardigan Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
03 Leather Satchel Soft, worn cross-body, obviously used. Budget Splurge
Splurge Price on Amazon Leather Satchel Leather Satchel Sold on Amazon Budget Price on Amazon Leather Satchel Leather Satchel Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
04 Round Sunglasses Thin metal frame, tinted lens. Budget Splurge
Splurge Price on Amazon Round Sunglasses Round Sunglasses Sold on Amazon Budget Price on Amazon Round Sunglasses Round Sunglasses Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
In this look 4

pieces · current prices are shown on Amazon

How to actually wear the Annie Hall look

Buy menswear, don't buy womenswear that looks like menswear. The whole effect comes from the fit being genuinely wrong — a shoulder that's too wide, a sleeve that's too long. The layers are shirt, waistcoat, tie, then jacket if you want it. All four is the full reference; shirt-waistcoat-tie is enough. Trousers are wide, high-waisted and in khaki, olive or grey. Not jeans, and definitely not slim. And the hat closes it — a black or dark felt hat with a defined brim. Keaton's version is what makes the outfit read as a decision rather than as borrowed clothes, which is a nice irony given they actually were borrowed clothes.

Written and edited by · Updated 16 August 2026

Filed under Annie Hall Borrowed Menswear 1970s

More looks to steal

№ 54 Almost Famous PennyLane 1973, on tour 8 pieces Shearling-Trim Coat · Flared Jeans · Round Tinted Sunglasses

Every wardrobe in the archive

As an Amazon Associate, Screenfits earns from qualifying purchases. Prices and availability shown are accurate as of the time of publication and are subject to change. Product images and titles come from Amazon.