Dressing Like the Men of “The Sopranos” Will Never Go Out of Style

Get yourself a pair of pleated trousers, a striped polo shirt and hop aboard the Stugotz

August 25, 2020 8:43 am
Tony Soprano: Style icon
Tony Soprano: Style icon

Nota bene: If you buy through the links in this article, we may earn a small share of the profits.

Like anyone with taste, I’ve been re-watching The Sopranos during quarantine. As a card-carrying Italian, I’m proud to say that I’ve seen The Sopranos roughly four times — three times through in its entirety and once watching along with a family member, catching episodes as they experienced it for the first time. Re-watching during quarantine got me thinking: How would Tony and the gang dress if they were handling collections and taking their goomahs out to dinner these days? How can an average un-made man achieve the same level of finesse and bravado as Syl and Paulie out for a night at the Bada Bing? Or Tony at one of his famous cookouts?

We’ve already talked at length about the appeal of the gangster knit: a lightweight sweater worn with trousers or even under a suit jacket. It’s a favorite of the men of Scorsese films, but I personally associate it most closely with Tony Soprano. Tony’s wardrobe boasts a proud collection of these knits, and it would be an infamia to put together a hypothetical closet of Sopranos-inspired designer fits without them. I could see Tony wearing this Anderson & Shepperd colored cable knit sweater with a pair of pleated — always pleated — trousers, loafers and even a jacket for a night out with Carm. For his more casual affairs, Tony swears by a polo shirt, and a knit version of this classic Soprano staple will always be a good choice, like these color-blocked Luca Larenza polos. For an afternoon in the back room at the Bada Bing, I’d put Tony in a Z Zegna linen and cotton mix long-sleeve polo (again, of course with his signature pleated trousers), or a long-sleeve polo in coffee-colored silk from Scaglione. For an afternoon of golf, cigars and cunnilingus jokes, might I suggest (to you, or Tony) this Topman blue pointelle knitted polo shirt. A cashmere Gabriela Hearst polo makes the bold choice of foregoing buttons, but I’d like to think I could convince Tony to give it a try. 

Luca Larenza Instarsia-Striped Polo Shirt

If a gangster knit isn’t your thing (you’re wrong, but OK), Tony’s collection of button-ups is also uniquely styled — a delightful mix of lightweight solids that move effortlessly on his foreboding frame, and more traditional-looking, bowling-style shirts with rakish patterns and color paneling. This striped Todd Snyder button-down sweater is perfect for an afternoon panic attack over some grilled meats, and a Luca Larenza printed shirt would pair nicely with a captain’s hat for an afternoon on the Stugotz. I could easily see Tony in a refined open weave Santillo 1970 shirt, holding court outside Satriale’s. 

For an over piece, Tony usually wears that style jacket that every Italian man wears and I don’t have the language to describe, per se, but you know what I mean; it has a narrow waist that sits right above the waist of their pleated pants and a small collar and it comes in a bevy of fabrics — leathers, polyester. It’s usually navy though sometimes it’s a taupe color, and his wife probably got it at Macy’s. But for a more refined take on the Italian dad jacket, might I suggest something like a modified bomber style leather jacket from Aero Leather Clothing, a Schott black leather moto jacket or even a suede number from Ami

Schott Black Leather Moto Jacket

Now, we have to talk about Tony’s pants. While the modern man typically leans for a slimmer trouser, a made man in Tony’s gang would never be caught buried under a bridge in such a cut. Tony’s pants are always pleated, at least a mid-rise, with a classic-fitting leg, and while this kind of cut might be hard to come by from today’s top designers, something like a pair of Timothy Everest slacks could fit the bill. For the trimmer gangster, a higher-rise pleated trouser like these from Edward Sexton could lend a high fashion twist on the waste-management aesthetic. 

Timothy Everest Sepia Linen Pleated Compact Trouser

And of course, I’d be remiss if I didn’t mention Tony’s loungewear — we are in quarantine, after all. Can you even call yourself a Sopranos fan if you don’t immediately think about him walking down his driveway in that white robe when someone mentions the show? The white robe is an interesting sartorial choice for Tony, too — even when he’s disheveled or hungover, or reeling from his depression, his robe looks like Carmela has just bleached it; there’s a neatness, control, and consistency even to his undress. Tony’s looks like a traditional terry, but to elevate the look, I’d opt for a Derek Rose white cotton robe

Derek Rose White Cotton Triton Robe

I would of course be remiss if I didn’t talk about the rest of the gang. There’s Syl, who is arguably the boldest dresser of the group — usually opting for double-breasted suits cut with wide lapels that make him almost look like a caricature of himself. To bring Syl out of his Scarface phase and into something a little more high fashion, I’d put him in this Tagliatore camel colored double-breasted jacket with a black trouser, and for the warmer months he would look great in a jacket that’s a blend of silk, linen and wool. I’d pair his bold jackets with characteristically bold shirts, like a long point-collar shirt (whenever you’re able to be out of the U.S. again, look up Edward Sexton for one of these). And while I’m usually firmly against contrast collar shirts, if anyone can pull one off it’s Syl, like this pink Cordone one.

Cordone 1956 Pink Cotton Contrast Cuffs Shirt

Then there’s Paulie — arguably the most casual of the group (with the exception of Christopher, maybe). We usually see Paulie in a short-sleeve button-up and slacks, or some kind of tracksuit — and of course, the Paulie Gautierri white loafers. I’m thoroughly obsessed with this Hansen short-sleeve twill button-down shirt and I’d love to see it on Paulie with the top button undone, revealing a very on-brand white tank. For more formal events, Paulie is known to rock one of my favorite looks on a man: a turtleneck and suit jacket combo. To bring his look into the 21st century, I’d put him in this rich Tom Ford turtleneck and a grey houndstooth double-breasted Rubinacci jacket. Both Paulie and Christopher love a good tracksuit, and while I cannot in good faith endorse this style decision, I can suggest some worthy alternatives, like Informale linen drawstring trousers (pair with a white tee); or these Z Zegna sports trousers (pair with a black tee).

Informale Navy Linen Model T005 Drawstring Trousers

Finally, we can’t talk about Sopranos style without talking about Junior Soprano, mostly because I think most of my male relatives wear the same clothing as he does, and it would feel like a familial betrayal to forget him. Junior is a relatively casual guy who likes to keep it comfortable and cool in his coke-bottle glasses and caps. For his days handling business from around the house, I’d put Junior in the quintessential staple of Italian grandfathers everywhere: the sweater vest, like a Merino wool one from Stenstroms, or this cashmere one from Rubinacci. For his days planning hits on his grandson and visiting Livia in her nursing home though, I’d opt for something like a Camiseria Burgos cotton shirt. And of course, we can’t forget the Corodo cap — like this one from Cappellifcio Biellese 1935. 

Capellifcio Biellese 1935 Brown Vitale Barberis Canonico Wool County Cap

Every time I watch The Sopranos I’m struck by something new — the first time I watched I obviously was just in awe of what an absolutely perfect show it was; the second time around, I realized I had become a grown Italian woman because I was attracted to James Gandolfini. After that, any time re-watching the show felt like visiting a beloved family member — gradually learning and appreciating new and subtle things about them while finding a profound comfort in their familiarity. Among these newfound points of appreciation was the feast that is the show’s clothing, and my quarantine re-watch has solidified this. It has proven to me the show’s status as a pillar of gangster style, a timeless ode to made men and their minions.

Subscribe here for our free daily newsletter.

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.