Let’s be candid: movie stars have a few advantages over us mortals when it comes to looking good. They have the genes, of course – matinee-idol magnetism is born, not made – plus, they reach theatre-goers’ eyes de-blemished by cosmetic artists, their innate good looks further enhanced by lighting and camera lenses.
And then there’s the clothing. The great screen icons are dressed with almost orchestral precision, thanks to the craft of stylists such as Louise Frogley (early Daniel Craig-era Bond), Michael Kaplan (Drive, Fight Club), Arianne Phillips (Once Upon a Time in Hollywood, Kingsman) and Ann Roth (The Talented Mr Ripley).
But us self-stylists need not despair: the ensembles worn by the best-dressed silver-screen dandies are there for the taking. Here are five male movie characters whose looks are worth studying — and stealing.
James Bond
OK, you knew he’d top this list: how could he not? With his scalpel-sharp tailoring, crisp shirts, effortless approach to casual garb and general air of insouciant grace (if you bottled it, you could start wars with it), 007 is the epitome of weapons-grade gentlemanly elegance.
His stylistic yen varies between eras and actors. Compare Sean Connery’s imperious, almost mathematically balanced suiting to Roger Moore’s safari-chic nonchalance, Pierce Brosnan’s sleeker, more corporate approach and Daniel Craig’s rugged wardrobe containing knitwear and Harrington jackets.
And whichever suits your own sartorial ethos, plenty of products at Anatoly & Sons are perfect for emulating the most stylish man ever to grace the silver screen. Moore’s Hemingway-esque adventurer in Moonraker and Octopussy is well-channeled by this unlined, unstructured herringbone safari jacket in ivory-hued linen. Craig’s Bond would definitely sport our cable knit merino wool and lambswool full-zip sweaters.
For the baccarat table, the single-color offerings in our tuxedo repertoire will lay some sartorial aces on the baize, whilst our navy blue and light blue Merino knit polos are great for channeling Connery or Craig’s Bond in tropical island espionage mode.
Dickie Greenleaf
Ivy‑inspired neatness and breezy coastal sophistication make a heady cocktail, when it comes to the style smarts of a wealthy fictional playboy played with suave swagger by Jude Law in the 1999 adaptation of in the 1955 novel The Talented Mr. Ripley.
Preferably undone as far as decency allows in your surrounds, Anatoly & Sons’ linen shirts – such as this, in Mille stripe blue, and this button-down version in tan – will help nail Greenleaf’s Mediterranean-chic. Our relaxed-fit trousers – such as these in a light grey ‘Cavalry’ twill by Drago, or these in a light grey material from Loro Piana’s ‘Tasmanian’ collection®, will help you feel like Dickie on a jaunt to Rome: especially if you indulge his taste for separates by having a jacket – with light, loose, and often breezy silhouettes, like those made for Dickie by Roman tailor Battistoni – made by our bespoke division.
Scottie Ferguson
The main protagonist in Hitchcock masterpiece Vertigo, played by James Stewart (of It's a Wonderful Life fame),
Scottie – unlike others on this list – exudes mid‑century restraint and old‑school charm. His inclusion here really underpins our ethos – the belief that truly elegant dressing is eternally relevant and immune from passing fads.
But contemporary flourishes can complement timeless classicism: hence our shirt recommendations – the classic dress shirt in light blue classic cotton poplin weave, and this white alternative in cotton twill – both have semi-spread collars (a more contemporary alternative to Scottie’s pinned point collars).
These are truly versatile “base layer” garments, which will sit with unobtrusive elegance under this Fresco Suit in blue, or perhaps this alternative in a lighter glen-plaid pattern fabric from Loro Piana.
Jay Gatsby
Leonardo DiCaprio and Robert Redford are just two Hollywood greats who have portrayed a literary legend who, like Dickie Greenleaf, would favor Anatoly & Sons’ selection of linen shirts: although a wardrobe department attuned to his dreamy idealism might have clothed him in jauntier colors, such as bright pink (as seen with this button-down option), or its sky-blue sibling.
Our bespoke department would relish the prospect of recreating the West Egg lifestyle in garment form with the kind of cotton-blend, tailored summer trousers Gatsby favors: not to mention unstructured jackets in linen and flannel and, for the truly bold client, perhaps, a pink, wide-lapelled suit with 6×3-button double breasted waistcoat, as sported by Redford’s Gatsby in the 1974 adaptation.
Then it’s back to our accessory department, for ties – the bolder patterned options amongst our silk line – and pocket squares (check out our treatise on how you can arrange them). You enjoy a free rein with the latter’s color scheme: but make it clash with the tie as brashly as possible. Our selection of Medallion Cap-Toe Oxfords, in various leather hues, completes the look.
Sam "Ace" Rothstein
Robert De Niro’s slick gambling czar in Casino dresses like the slightest wrinkle might cost him a fortune at the tables, his late-’70s Las Vegas bravado made up of a mélange of pastel suits, razor-creased trousers, colossal collars and meticulously shaded ties.
But Sam’s sartorial approach is also one drenched in discipline: controlled loudness, meticulously tonal in nature, deliberately matched, and always pristine. To channel him through Anatoly & Sons, start with our blue wool-silk-linen blend sport coat (seasoned sartorialists will note the Milanese Buttonhole in gracing that notch lapel). Pair it with our aforementioned charcoal grey twill trousers to max out the Rothstein-esque grace when it comes to contrast.
While we stop short of the exaggerated ’70s spread collars Ace favors, our silk-cotton poplin dress shirt in light blue will, paired with the jacket mentioned above, emulate Ace’s penchant for tonal (aka monochromatic) dressing while also honoring the crisp luminosity of his wardrobe. Likewise, our linen-wool tie in denim blue.
Remember to sport the look with confidence, safe in the knowledge that Rothstein’s wardrobe isn’t flashy – it’s all about order, clean lines and perfect coordination.
Jacob Palmer
Ryan Gosling’s smooth-talking sartorial savant in Crazy, Stupid, Love conducts himself like he’s permanently gliding through a world of oak panels and soft jazz: His whole demeanor is about refinement without fuss: razor-clean lines, fabrics that behave themselves, colors that speak in quiet confidence rather than shout from rooftops.
Channeling him through Anatoly & Sons probably begins with the same white version of the shirt – one that behaves impeccably under a jacket – we’ve assigned above. If going jacket-less, juxtapose it with slim, impeccably cut trousers – residing in the Goldilocks zone between tight and baggy– perhaps in a light gray in a ‘Cavalry’ twill fabric from Drago or navy blue (such as these, in a fabric from Holland & Sherry’s Royal Mile Collection).
Or, if going suited (but tieless, in keeping with Jacob’s preference), our modern charcoal suit packs the close, contemporary silhouette he favors. These black medallion cap-toe Derbies complete the look, or perhaps consider a small deviation from all the understated sobriety, here, with these black tassel loafers. If opting for a discreet pocket square, stick to the presidential fold, just peeping out of the pocket.
Subtlety, after all, is your friend: especially when emulating some of the most iconic stylish men in (fictional) history.
