Meet the forgotten Premier League star who has become the world's most fashionable manager

Daily Mail​

04-06-2025

A former Everton and Wolves midfielder is grabbing the headlines as one of the most fashionable managers in world football right now.
The ex-Premier League midfielder endured a miserable two seasons in England, playing only 17 times in two years.
Segundo Castillo, manager of Ecuadorian side Barcelona Sporting Club de Guayaquil, has captivated audiences with his stylish attire on matchdays.
The former Ecuadorian international with 88 caps stole the show in a dynamic black and white patterned floral dinner jacket during the Copa Libertadores group stage.
His outfit featured a striking red bow tie with a matching red rose and pocket square on his left-hand side.
Castillo's fashion sense couldn't prevent his side losing 1-0 to Peruvian club Universitario.
The Ecuadorian's elegance did not match with his playing days, known for being a fiery defensive midfielder who's played across four continents.
Castillo briefly graced the Premier League but failed to make an impression during his two loans at Everton and Wolves in the 2008-09 and 2009-10 seasons.
His forgettable two seasons under David Moyes and Mick McCarthy yielded little game time whilst on loan from Serbian side Red Star Belgrade, scoring once for Everton in the UEFA Cup.
The culmination of his loan spells led to the then 27-year-old leave England for his home country before stints in Mexico and Saudi Arabia.
The midfielder's enjoyed a solid international career, playing every minute for Ecuador in the 2006 World Cup campaign, reaching the second round for the first time in their history.
Castillo has had a solid start to his managerial career with the 42-year-old's strong 50 per cent win rate for Barcelona SC.
Yet, his looks have garnered more attention than his results on the pitch with the manager being coined as 'Sir Second Castle' for his classy looks, the direct Spanish translation of his name.
Barcelona SC grabbed the headlines by knocking out ex-Manchester United flop Memphis Depay's Corinthians 3-2 in the third round of Copa Libertadores qualification.
Progressing to the group stages, Castillo donned a distinguishable 19th century black and white dinner jacket with black trousers.
'Sir Second Castle' continued his chic looks in his side's 1-0 win in the group opener against fellow Ecuadorian side Independiente del Valle.
Castillo opted for a more traditional all black dinner jacket with a white shirt as Bryan Carabali's early goal secured the three points for Barcelona SC.
The following group game Barcelona SC took on Argentina giants River Plate, known for harbouring immense talent such as ex-Manchester City striker Julian Alvarez and Chelsea's Enzo Fernandez.
A boring 0-0 draw was countered by Castillo's extravagant pastel pink dinner jacket, a two-piece accompanied with a pink bow tie.
'His unique style has made him an icon within South American football', said Telefe when analysing the 'Mortero's' looks.
🤵🏆 ¿Lujo? El de Segundo Castillo, entrenador de @BarcelonaSC: así se ve un partido de CONMEBOL #Libertadores. #GloriaEterna pic.twitter.com/60PpBBT9DD
— CONMEBOL Libertadores (@Libertadores) March 6, 2025
😎 Not even the rain will stop Sir Second Castle from showing up in style! 👏
🏆 CONMEBOL #Libertadores pic.twitter.com/CGuwcQUdUS
— CONMEBOL Libertadores (@TheLibertadores) April 2, 2025
In one of his first games as an initial interim manager against Cerro Porteno, Castillo wore a flat cap reminiscent of the Peaky Blinders.
His dark grey cap matched his smart waistcoat, complimented with a black shirt and black trousers.
His exuberant fashion sense stretches to both on and off the field, as seen when the former defensive midfielder rocked up to vote in unusual attire.
Voting at the April 2025 Ecuadorian general election, Castillo arrived in a traditional Saudi Arabian shawb, an ode to his playing days at Al-Hilal.
Castillo placed his vote into the ballot box, giving a thumbs up the camera in his Saudi Arabian outfit.
In an interview with Diario Extra, Castillo revealed that his wife is the key decision-maker behind his stylish looks as his 'technical assistant' for his fashion.
'My wife is the one who helps me regarding the outfits. If she thinks I'm handsome, that's more than enough.'
He added that his on-field looks match the stature of his job: 'You must be on the same level as the place where you are.
'So, I try to put out a good image to my players and to the audience.' Segundo Castillo sobre su vestimenta: 'Mi esposa me ayuda a elegir los trajes' – link to interview article (translated the quotes from Spanish for you)
Looking into the future, Castillo touched on his dream to manage the Ecuadorian national team in the future.
The current Ecuadorian national side exudes talent with the likes of Chelsea's Moises Caicedo and Brighton's Pervis Estupinan.
Argentinian Sebastian Beccacece is La Tricolor's current boss with the national side's last Ecuadorian appointment back in 2015.