My Style: Matthew Singer
Photo: Christopher Fenimore for Fashion We Like
What is the biggest mistake one can make when getting dressed?
Overthinking your look — you don’t want to be that guy who has too much going on.
Please describe your style in three words.
Confident, clean, and classic.
Do you believe in role models?
Of course, who doesn’t?
What are your favourite fabrics?
Cashmere and linen, I want to be warm in the winter and cool in the summer.
Which city has the best-dressed men?
Florence, Italy.
Would you say that you are conservative or bold?
I would have to say I am boldly conservative. I always like to add a bit of twist to my look. Usually, I am the only one aware of what that twist is…
What are the rules in the way you dress?
Less is more. However, there was a time that more was more. The rules are meant to be broken.
Are there any style combinations that you object to?
Trying to pair your suit jacket with jeans. Gentlemen, invest in a separate sport jacket.
Celebrities and style...
Can be a great combination with the right stylist!
Name one garment/accessory that you can never have enough of?
My navy sport jackets, I have too many some say. I think I don’t have enough. I always travel with two — three at a time.
A man should always look like...
He put some thought into his appearance. The days of the “I just rolled out of bed look” are over.
Who taught you what you know about style?
My father for sure! He has great style. When I was a kid I don’t think I realised it, but thankfully I started to take notice.
How do you select your clothing every morning?
Good question. I start with my shoes, and everything seems to fall into place. Oh, and then I ask my wife what she thinks…
What is your biggest regret?
I don’t have any! It all happens for a reason.
The three essential things a man should know about style are...
Keep true to yourself, embrace it, but don’t overdo it.
Do you have any shopping rituals?
Not really, but once I break the ice, it’s bad news for my bank account. I have a hard time cutting myself off.
We will never see you wearing...
A party shirt.
What is the first thing you notice on a man?
Everything, my eyes have been trained to capture it all in one shot. Hey, it’s my job.
The one image that defined your approach to style...
I think it has to be my environment and not a specific image. I am always seeing elements of other’s styles and incorporating into my own.
The only article of clothing that a man needs to pay close attention to is...
His shoes. An ugly, unpolished shoe can do a lot to your look.
What are the most treasured items in your wardrobe?
My suits! I spend the majority of my time in them, so I make sure they are well cared for.
Is comfort an enemy of style?
Not always. A closed mind is the enemy. The most comfortable things I wear are my suits.
Who would you like to recommend for My Style?
My twin brother Spencer, I would love to compare.
The best words of advice you have ever heard?
Stay humble.
