Ranking The Most Stylish Characters On ‘The Wire’

Fashion isn’t exactly the first thing you think of when someone mentions HBO’s The Wire (available to stream anytime on HBO Now). However, when you consider a show with this kind of scope and this many characters, you start to see how their clothes help tell the story. From the polished looks of the elite ruling class to the battered scraps worn by people living on the streets and everyone in-between, here’s a ranking of The Wire’s most stylish characters.

8. Jimmy McNulty

Okay, starting at the bottom, Jimmy McNulty’s (Dominic West) sense of fashion begins and end with a thrown-together, perpetually rumpled outfit that’s draped in a cheap leather jacket. McNulty was all about his job as a cop in West Baltimore and couldn’t be bothered to waste his time with furniture (unless his kids were staying over), much less a sense of style. Still, there’s something undeniably classic about McNulty’s ‘just-rolled-out-of-bed’ look. For him, being real police is a full-time lifestyle and doesn’t allow for the luxuries… like ironing.

Best accessory: While his trademark smirk was definitely in the running, for McNulty, we’re going to have to go with the half-empty handle of Jameson that was always in his coat’s right pocket.

7. Proposition Joe

A first impression says a lot about you, and once the show first introduces Proposition Joe (Robert F. Chew) to help coach the East Vs. West Baltimore basketball game, he’s dressed to the nines. “Look the part, be the part, motherf*cker,” he tells Avon Barksdale (Wood Harris) after catching some flack for wearing a suit in 85-degree weather. While he mostly dressed for comfort, he would revisit the suit-and-tie look on occasion, because the man knew the importance of finding the right clothes to make a statement.

Best accessory: His fake clipboard. It just brought the whole thing together.

6. Ziggy Sabatka

A put-open dock worker who desperately wanted to kickstart a new life for himself as a big-time criminal, Ziggy’s (James Ransone) fashion sense could be most easily described as McNulty-chic. While he sported the same rumpled, cheap leather jacket, Ziggy took McNulty’s look to the next level with an assortment of famously bad shirts he’d wear underneath. Sure, he may have been in over his head just no matter what, but the guy knew how to throw an outfit together.

Best accessory: Can horrible criminal instincts be an accessory?

5. Omar Little

The perfect example of style-meets-tactical, Omar’s (Michael K. Williams) wardrobe consisted mostly of basic black, from his coat to his ever-present bullet-proof vest. You might have heard him coming by his whistle, but once everyone saw him coming, Omar proved that his look was inseparable from his persona — not to mention the perfect balance of form and function.

Best accessory: There’s a few choice items of his that would fit here, but Omar may have put it best when he said “Sometimes who you are is enough.” Indeed, Omar. Indeed.

4. D’Angelo Barksdale

When his uncle, Avon, helped pull some strings to help sway his trial in his favor, D’Angelo Barksdale (Lawrence Gilliard, Jr.) was eager to get back in the game. His job may have involved overseeing a small group of corner boys, but D’Angelo was always careful to look the part. But there was another side to him, too, the one that looked to break out not just from his cousin’s criminal empire, but from the only way of life he’d known. Still, even if he was only flirting with the idea of life on “the other side,” he always made sure he dressed for the part, regardless.