Dear Simon,

Many thanks for the invaluable resource of your blog when it comes to style. I started reading a month or so ago and am taking pleasure in devouring the wealth of information there is on classic sartorial menswear.

However, the occasions on which I am required to wear a suit are extremely limited (I am a student) and, while I cannot wait to see the day when I will be free to wear a suit more often and the doors this will open for experimentation, it would be of great help if you could provide some more information on how to dress casually, in terms of different ensembles one could come up with to avoid looking the same every day. The posts I have found most helpful thus far have been ‘The modern man needs a good blazer’  and ‘Reader question: what do you wear at the weekend?‘ I want to leave behind the hoodies and printed T-shirts of my youth and start dressing like a grownup, though not in a suit.

All the best,


Dear Alex,

I’ve had a think about this and I think I can summarise my main points about dressing casually in three bullets. There are many others around accessories, colour, texture etc, but hopefully those are pulled out in other posts.

1 Wear proper trousers

I wrote about this a couple of years ago in the post ‘Why men are scared of real trousers’. The key is to move away from jeans, though not abandon them entirely, and to make sure all such trousers have a simple, straight cut. Nothing fashion-led, nothing ripped or overly distressed, just a simple style and fitting well on the waist. With jeans, try buying raw denim that will then gently wear with you and how you wear them. I like Albam myself, and they’re good value.

With other trousers, get some good chinos. Start with the classic cream and then expand into tan, green and brown. Again, simple with a straight cut. The difference between smart and casual can be demonstrated by Incotex, my favourite brand here. Their standard range is smart and clean, but the Red line is distressed and far more casual as a result.

2 Wear a jacket or substitute

It’s easy to make do with wearing a shirt or T-shirt the whole year, just putting on a jacket if it’s cold outside and a sweater if it’s cold inside and colder outside. Don’t. Wearing a jacket or any substitute – cardigan, vest, light sweater – instantly elevates you above scruffy teenager.

Obviously, a jacket is the best of all. If tailored, it can be soft and casual in cashmere or washed cotton (try Boglioli). If not, many stores now do jackets in cotton or wool jersey – Zara and Reiss do them, and Massimo Dutti is a good source for anything a little more mature in style. And at the higher end, go to Trunk Clothiers and try the aforementioned Boglioli as well as Barena and others. Hopefully the images above and below demonstrate some of the potential here.

If you were to invest in one thing, it should be a tailored or made-to-measure jacket that could go with any casual trousers. Perhaps a pale grey herringbone cashmere?

3 Buy good shoes

These don’t have to classic lace-ups. A smart pair of suede Adidas (don’t play football in them!) or leather Common Projects can be very smart. But lace-ups elevate you immediately to the level you want to play at. Buy a pair of brown lace-ups that will seem too expensive (Crockett & Jones, Grenson, Alfred Sargent), look after them, and wear them with casual trousers and even suits. If you rarely wear formal clothing, the second pair should be exactly the same, but in suede. Just as stylish, not quite as formal.

I hope that’s helpful Alex. There’s so much to say… (also consider collared shirts, including polos; most men look better in a polo or proper shirt than a T-shirt).