Tom Landry
Dallas Cowboys
We'll say this once (and maybe a few more times): Before the days of corporate sponsorship and space-age athletic apparel, coaches used to look like they meant business. Just look at Landry. When your fedora is placed next to your name on your team's Ring of Honor, you've probably hit on an iconic piece of style.
Paul Brown
Cleveland Browns, Cincinnati Bengals
Between Landry and Brown's badass suit-with-sweater-vest look here—and their combined 5 NFL titles—maybe sartorial sense really does affect winning percentage.
Mike Ditka
Chicago Bears, New Orleans Saints
We appreciate Ditka's home-team enthusiasm—he still wears this get-up when the Bears are on Monday Night Football—but there are better ways of showing your pride than that sausage-casing sweater vest...
Hank Stram
Dallas Texans/Kansas City Chiefs/New Orleans Saints
...like this. When modern-day coaches wear their official NFL hoodies festooned with team logos, they look like Nascar drivers. When Stram stitched one to his navy blazer, he gave Kansas City a dose of East-Coast prep.
Bum Phillips
Houston Oilers, New Orleans Saints
With his Texan roots and trademark Stetson, Bum Phillips was the poster child for fearless personal style. How else are you supposed to dress while coaching the Houston Oilers?
Bill Belichick
Cleveland Browns, New England Patriots
Belichick's, on the other hand, is a look that shouldn't be trademarked so much as made illegal. We know you're an esoteric evil genius and all, but would it kill you to put some sleeves on those?
Vince Lombardi
Green Bay Packers, Washington Redskins
Out there on The Frozen Tundra of Lambeau Field, Lombardi set the bar for cold-weather coaches: When conditions are sub-zero and you're asking your boys to grind out that last yard, you've gotta lead by example...
Mike McCarthy, Mike Singletary, Wade Phillips, and Others
...unlike these guys, who seem to run for the Antarctic-station gear every time the kickoff temp nudges fifty. It's hard to take play calls seriously when they're coming from Coach Stay Puft.
Mike Nolan and Jack Del Rio
San Francisco 49ers and Jacksonville Jaguars
In 2006, Del Rio and Nolan petitioned the NFL to let them wear suits, leading to these custom Reebok-designed numbers. A petition to wear suits? No wonder they call it the No Fun League.
John Madden
Oakland Raiders
All the king's horses and all the king's men... denied all responsibility for the Humpty-Dumpty pants John Madden wore throughout the '70s.
Sid Gillman
Los Angeles Rams, Los Angeles/San Diego Chargers, Houston Oilers
If NFL Films ever immortalizes you for revolutionizing the downfield passing attack, you'll wish you were sporting something as sharp as Sid's notorious bow-tied style—just check out the man's Hall of Fame bust.
When trying to lead a platoon of purpose-built, 300-pound athletes to gridiron glory, it's important to look the part. With the NFL season in full swing, we decided to take a look at the best- and worst-dressed coaches in pro football, past and present
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