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).
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you forgot ditch the T-shirt. Maybe it is just me but I think a well fitted polo, or casual collared shirt (chambray, oxford, etc.) are really important to looking more sophisticated in ones casual dressing.

Alexander Hugh Jarce

Hello Simon, Some great tips for Alex here,the shoes really make the difference. That is for sure. I don’t like chinos myself so I steer towards different coloured denim such as rust or green,again simple cut styles and avoid the overly distressed.


Like Alex,

I too loved the “Everyman needs a good blazer” post. I recently followed that advice and got a Navy hopsack blazer w/ genuine horn buttons. It is so versatile. Now I would like to focus on the above mentioned unstructured jacket. Keeping in mind that I have a navy blazer, what color would you recommend for this jacket to achieve maximum versatility?

wu ming

Hi Simon

What’s a reasonably price for good woollen trousers? And how much is too much?I saw a pair of black striped trousers with side fasteners in Hackett, but isn’t £200 a bit too much for RTW?


Hi Simon,
Permanent Style generation keeps rising!
Lately,I have started pondering on the kind of event you could well envision that would be an occasion for all these folks out there to meet and share their experience and pleasure as fellows!
It might be a rewarding & enjoyable moment!


Yes, this could be a very good opportunity indeed, Simon. Yet there would be a need to draw lessons from all previous experiences attempted so far in this field – by the way not that much – and to see about how what you have been adumbrating could serve as an exploratory tool for a more workable project centered around menswear. Not only is London a strategic site, but there are also enough stakeholders who might well have a real interest in any sound venture designed to give more attention to menswear in today world. From my perspective, Permanent Style could be instrumental in many respects. Just stick to what you already have in mind and keep it in progress.



what are your thoughts on an unstructured cotton jacket grey herringbone.. Its a bit of a combination of the jacket advice from your post


Can you recommend a weight for year round wear (could medium grey herringbone be worn year round)? Also, is there a good weight for summer wear? Thanks


Hello Simon

Great article, it’s answering a problem tht many young guys have. I have recently started to completely change my wardrobe and style because I finaly have managed to lose enough weight.
So after 6 months of studying men chlothing I’ve bought theese items so far(for fall-winter):

5 sportcoats: 4 fall winter weight wool from Suitsupply(navy, blue, light grey and a houndstooth brown) and 1 cotton double breasted one from Boglioli(navy)

6 pairs of pants: 2 jeans(7for all mankind, I like they are slim and have no contrast stitching), 2 flannel Incotex trousers(gray and navy), 2 Tommy Hilfiger chinos(navy and beige)

10 shirts( white, light blue, striped etc) from Suitsupply, Barbra Napoli, Ralph Lauren purple label(with high discounts)

7 pairs of shoes: 2xc&j tassel loafers(both suede, dark brown and polo suede), 2xC&J tetbury chukka(both brown, one calf one suede), 3xLaslo Vass( brown calf 3 eyelet derby,brown calf full brogue, dark brown double monks, all on U-last)

and all kinds of accesories(ties, pocket squares, belts etc)

Now I still have about 1500 euros from my new wardrobe budget. If it’s not too much trouble, could you tell me what else should I get? I mention that I already have a tan trench coat and a overcoat and I will not buy any more untill the sales in January.

Thank you


Thank you for the quick answer, I will give the Drake’s cardigans a look. I’ve just recieved 4 Drake’s ties and I could not be more pleased about their quality. I am by no means an expert in quality, but they just look so well made and really luxurious


I meant compared to the crappy Massimo Dutti and Zara ones I had before, they seem from another world. I should mention that two are wool-silk, one cashmere, one silk and more on the casual side than what I think would go with a sharp suit(as I really want to start wearing ties with casual outfits). I ordered the Drake’s ones based on one article on this site…


Simon, this has been one of your most wonderful blog posts. I am still at university, and reading this post makes me feel like a father figure or older brother is giving me advice. I was wondering, what is your opinion of Gant? Particularly, their shirts? Where is a good place to shop for reasonably priced shirts- the kind that would go with the casual dressing you have described. Thanks, Aldous Bertram.


Never thought I’d read a plug for Common Projects on Permanent Style

Fredrick Parker

As always, spot on!


as much as I agree with Simon, I’d like to add my own little bit of advice- watches!

Just like wearing good clothes and cheap shoes is a no-no, so is a poor quality watch- make an investment, you should be spending at least £1000 on a watch, the best advice is to buy nearly new, or a vintage Omega or Rolex (or Patek if you can afford it). Money spent on a quality watch is almost never lost.

If you don’t want to go the mechanical route, get a high end Japanese quartz, The Citizen or Grand Seiko, either run from £1200 upwards, depending on metal. They may seem expensive for watches wearing mundane brand names, but the quality even surpasses some swiss high end brands, and they’re hand finishes and assembled. They also have suberb mechanical models. You’ll have to get them from a Japanese dealer like Higuchi as they don’t sell outside of Japan (apart from some Grand seiko).

You can carry off being stylish driving a natty old car, but not wearing a cheap watch- it reaks of bad taste.



I can’t agree with this in the slightest – it’s just snobbery. There are many of us who can’t afford to be ‘spending at least £1000 on a watch’. I fail to see how this entails that we must have bad taste. Some of the most stylish and tasteful people I know are ones that come form very humble backgrounds and almost exclusively buy their clothes from charity shops. Clothes are different to watches anyway – they’re permanently on show, whereas a watch is (or should be) hidden, so I don’t agree that wearing an inexpensive one should constitute an act of bad taste.

Ian Arnold

Yes! In any case the smart phone has replaced the watch as the number one gadget to own! I’ve got a simple DW watch where you can swap the strap according to your other leather accessories. You have to move with the timed.

Totally agree with paying a bit more for shoes though! I’m not sure of the value of t-shirts Polo shirts, shirts and jeans beyond a certain price point though!


It is quite absurd to suggest a student should purchase some 1000£+ watch, likely costing more than their entire wardrobe. Not to mention that you can buy a decent watch for less than 200£, including automatic, e.g. Orient.

Bertie Wooster

Hi Simon

Should business suits have straight or slanted pockets or does it not matter? I’ve seen both styles on Savile Row. Or are slanted pockets only
meant for sports/tweed coats and not for city wear/dinner/smoking jackets?

Best wishes



I agree with you about proper trousers and good shoes, but cannot see that putting on a jacket ” elevates the leve of clothing AT ALL.
The tieless-but-jacketed look is an abomination.


Hi Simon,

I was wondering what the formality difference is between a pair of jeans in the style you would see in any department store vs something like Hollywood trouser jeans if they use the same denim? Also, how would you style each one?


Dear Mr Crompton,
Do you have any other RTW-recommendations than Boglioli? In my mind their jackets are just too short.


In my experience Caruso does very good RTW jackets with a less trendy cut.