Spurs fans were divided on the merits of Andre Villas-Boas but one thing you couldn’t argue about was his dress sense.
A sharp, slim-cut dark suit, crisp white shirt and a skinny tie were the AVB trademark. I talk about him in the past tense as if he were dead, when in reality he could well end up elsewhere, perhaps as the manager at AC Milan, where you would expect him to look even more magnificent.
When it all went wrong for Villas-Boas at Tottenham, it might not be a coincidence that it came at a time when he had let his standards slip. As autumn turned to winter, so the Portuguese warmed himself within the confines of an official club coat.
It was a plasticky-looking affair, of the type that would be worn for reasons of practicality over style. Waterproof probably, as if it’s better to be dry than to look good.
Obviously it didn’t suit Villas-Boas at all and I’m going to stick my neck out and speculate that it might be the chief reason that he lost control of the dressing room. If he’d held firm against corporate branding and insisted on wearing a Crombie, the man might still be in a job.
In sartorial terms, Spurs have gone from the sublime to the ridiculous with their decision to sack AVB and promote Tim Sherwood to the hot seat. Since taking the job, the new manager has rarely been seen without a tracksuit on.
I’m not sure if this is genuinely what Sherwood wants to wear, or whether it’s a deliberate aim to distance himself from Villas-Boas and position himself as the "football man" that Jamie Redknapp keeps describing him. Either way, it doesn’t reflect well.
The one exception came on Boxing Day, in the match against West Brom. Sherwood wore a V-neck jumper -- quite probably a Christmas present -- with a tie. He certainly looked smarter but this is a look that has its genesis in the playground and is not suitable for a leader of men. Can you imagine Winston Churchill wearing a tie under a V-necked jumper? No.
On Saturday, Sherwood took on the king of the tracksuit managers -- Tony Pulis -- in a battle to see who could dress worse. Though Tottenham won the game, the Crystal Palace manager, who is 55, came out on top in the battle of the sideline looks, thanks to his penchant for also donning a baseball cap.
Sherwood is 11 years Pulis' junior. Forty-four is an age where you really shouldn’t be wearing sportswear unless you are actually participating in a sporting activity. While it’s true that Sherwood jumps around a lot on the touchline, there’s no reason he couldn’t do so while dressed as an adult.
Of course, there have been plenty of managers over the years that preferred a tracksuit to a real suit. None of them looked good, with the possible exception of Brian Clough and his green sweatshirt, but then he was an eccentric.
One of the other problems for a sports-casual dressed manager, is what to wear on their feet. Many of them wear boots, which always suggests that they were in two minds as whether to name themselves as one of the substitutes. Sherwood has mostly been wearing white trainers, which makes him look like Jerry Seinfeld.
If he wants to be taken seriously as the manager of Tottenham Hotspur and not viewed as a sacrificial lamb with an 18-month stay of execution, then Sherwood needs to at least look the part.
Playing 4-4-2 every week was always bound to paint him as a philistine in this age of tactical boffinry and Sherwood is doing nothing to assuage such fears by dressing like a physical education teacher.
Image is everything these days. Sherwood needs to get himself down to London's Saville Row and start dressing like a man with a seven-figure salary and a position of authority.