How to Pull Off a Grey T-shirt like Simon Cowell

So, why is it that most guys look shit in a plain grey t-shirt while Simon Cowell looks fabulous without making much effort? Well, if that’s any consolation to you, Mr Cowell doesn’t look particularly great in a classic suit, so he had to develop a style that fits his body shape. Let’s look at Simon Cowell’s fashion tips. Not that he’s shared any, it’s just my observations.

Develop your upper body

Simon Cowell in Grey

Simon Cowell in Grey

If you’re not particularly tall, you can build up some sex-appeal by developing muscular arms and shoulders. Look at Popeye, he’s a good example 🙂 Simon Cowell isn’t afraid of wearing short-sleeve tees or sweaters with rolled-up sleeves because he’s got good arms to show.

But most importantly, CONFIDENCE! Simon looks good because he’s confident.

Choose boot-cut jeans

Boot Cut

Boot Cut

I don’t normally advise people to buy trousers that are too long for them but if you’ve got a similar body shape, you may find this beneficial. Get some slender shoes with a decent heel and wear boot-cut jeans that hide the heel.

Be sure to try them on first to determine if they don’t crease too much at the front. Otherwise, as you’ll see further in the article, it may actually shorten your legs.

Iron and keep clean

White and Ironed

White and Ironed

The main difference between Simon wearing a plain t-shirt and an ordinary person wearing one is that Simon wears great quality, perfectly ironed and clean tees. No matter how hard you try, you won’t be able to copy his style by choosing a £3 t-shirt from Primark.

The quality just isn’t there. Look at the white t-shirt he’s donning in the pic. Yep, there are some creases but they are the natural flow of the silky (expensive) material. Trust me, this has been properly ironed! No excuses, ironing is not as difficult as it may seem.

If you have to wear a suit…



… well, there are situations when you can’t avoid wearing a suit. Besides, suits are great, so you don’t have to renounce suits.


Don’t look like him

Just be clever and adjust, otherwise you may end up looking like Dollman. Mind you, it would be a feat to find a ready-made suit that really fits Simon’s body type.

I bet the odd occasions when he’s actually wearing a suit, he wears one that was tailor-made. In this case, though, the tailor hasn’t been particularly skilful. I found several mistakes.

Before and After

Simon Cowell Before and After

Simon Cowell Before and After

Ok, so here we have our Simon nicely vectorised so that I can adjust him on the go. The left pic is how he looks in his original suit and the right one is how he should look. So here’s what I did to him.

  • Lengthened the sleeve. Actually I did so both with the shirt and the suit. You still want a quarter of an inch of white material to stick out of the jacket’s sleeve. Don’t overdo with the sleeve length. Any longer and you’ll come across as desperate.
  • Padded shoulders. You may think that Dale Winton is the last person on earth to wear padded suits but you’re wrong. Many tailor-made suits have shoulder pads.They’re not as big as in the 1980s that’s why you don’t realise they’re there. If you’ve got a decent length neck (like Simon does) you can afford some padding which will draw attention to your upper body.
  • Colour, colour! By adding a brightly coloured neck tie, you achieve two things. You draw attention to your upper body (away from the short legs) and you introduce a vertical line that makes you look even taller.
  • Pockets where they should be. Simon Cowell is right in thinking that lower pockets should sit above the hips, however, he’s overdoing it. I’ve placed the pockets slightly lower and it already looks better.
  • Mind the break. Simon only wears boot-cut trousers so he’s naturally gone for a massive break on suit trousers as well. And this is a mistake. When denims break on top of a boot, it looks good because it’s a stiff material.Your suit is much lighter, so the break will be more prominent and this can make your legs look shorter. So when it concerns suit trousers, go for minimal break or no break at all. This will make you look more slender.

Ok, that’s about it. Don’t be shy, post your own Simon Cowell look and I’ll share it with the world!

Expert verdict: Definitely Dude! :mrgreen: Although I’ve been a bit harsh, I do consider Simon Cowell a sort of a fashion icon.

Pic credits:
Vector Simon image by Arvid Linde

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6 responses

  1. Lol, Simon vs. Dollman, this is just brilliant dude, I can’t look at him without laufghing any more. I’m not a big fan of bootcuts but guess it works for our little Simon.

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