Kind of showy: All black jacket and jeans

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On Permanent Style we’ve always talked about dressing with subtle elegance - clothing that makes the wearer appear simply well dressed.

This is still the style I get most pleasure from. It's a matter of good fit, quality materials, and tasteful combinations. It's the way I dress the most, and the one most people I know aspire to. 

But part of my journey with Permanent Style has always been about experimenting with other styles, and exploring how they relate to this central, elegant core. 

Some, such as today's outfit, push away from the safer end of the subtle/showy spectrum: they're consciously more of a 'look', deliberately standing out. Playing with styles like this is a sign of being open-minded, I think, but is also something a lot of style niches struggle with, perhaps particularly classic menswear with its rules and traditions.

As far as Permanent Style is concerned, these outfits are a sign of expanding what we cover, rather than shifting in any particular direction. The circle grows; the centre is unmoved. 

Expanding on that theme, I wore this all-black outfit to Pitti Uomo because it’s a nice opportunity to try things out. Everyone’s aware of this, everyone’s interested in what others are wearing, and you're often interested in the opinions of your peers. 

That’s very different, to my mind, from the garish clothes some still wear to get as much attention as possible. For me and those I know, it’s about quality, not quantity; seeking the thoughts of those you respect rather than being the centre of attention. 

The other issue with more unusual outfits like this, is there are fewer places you can wear them, and perhaps a smaller number of people who would. They’re not as universal as some of what PS covers. 

But I would wear this all-black outfit to some evening events and indeed have done so recently. Not fashion events either: a friend’s dinner party, a celebratory evening out. 

It’s a little showy for a dinner party - you might have someone comment that you look like a rock star (or more likely, like you’re trying to look like a rock star). Something similar in navy would always be easier. But again, it depends how subtle or showy you are as a person, and want to appear. 

One more angle on this, before we talk about the clothes. This feels like me, in this place and time; it feels appropriate. 

At this point in my career, in this place (Pitti) it feels natural for me to dress in this manner. It wouldn’t have done 10 years ago; it wouldn’t do now if I was having a birthday lunch with my family. But there, now, it fits. It’s not too much of a reach. 

This doesn’t mean that a much younger person, with a very different standing, couldn’t rock the look. But I wouldn’t have done. Me, myself: the person I am, with this personality. 

As big a mistake as any other when you're first getting into clothes, is trying to look like someone else. Everyone should explore, everyone should push themselves, and often it takes a while before something feels natural. But some things just aren't you, at least today. 

OK, so now the clothes. Hopefully some of that chin scratching was interesting. 

The jacket is my black hopsack from Paolo Martorano, worn with washed black Levi’s. The jacket is not a natural one, not the easiest, to wear with jeans because it's quite sharp. 

But that matters far less when you’re wearing one colour like this - monochrome. There’s less contrast - everything recedes into silhouette and texture. And it also matters less because we’re aware this is a showy look anyway - not the subtle jacket-and-jeans discussed previously on PS and which most readers will aspire to. 

It's also worth noting that I would rarely button the jacket here, which makes that sharpness less relevant. It would seem odd to, in a look which while clearly considered, is also so laid back.

The shirt is a washed denim from 100 Hands (a prototype we’re working on). The shoes are classic Sagans from Baudoin & Lange. The belt is alligator from Rubato and the sunglasses are vintage gold-rolled Caravans. 

The unusual piece is the bag, which is actually the packaging I received belts in from Japanese maker Ludens recently. I’ve been exploring small day bags like this - as with the vintage cartridge bag - and this pouch with its drawstrings works pretty well. 

The only issue was that the suede initially shed a little, leaving little bits on my jeans. But it settled down during the day and wasn’t a problem by the end - so clearly something on the surface, that perhaps I could have brushed off before use. 

It’s the same suede that Ludens has used for cross-body bags at Bryceland’s, which gave me the idea. Those are only available made to order in the Hong Kong and Tokyo stores, in this sand colour and black, and my bag is not available separately. But I know Ben in London is hoping to get some in at some point.  

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Hi Simon,
This combination looks good on you although not necessarily something I would wear, your narrative is spot on, n my opinion. I think the key word here is appropriate.(occasion, setting, context in a broad sense, etc.), being able to stand out, whilst remaining subtle. . Without going into detail I found this to be the case with some holiday clothes, which seemed right in a beach resort setting, but wouldn’t wear casually in and around London where I live.
Interesting to see a subtle pushing of the boundaries.


Interesting look, Simon. I don’t have a black jacket (and I don’t think I’ll ever get one) but I could see myself wearing everything else. Changing the jacket for a dark navy, dark olive or brown tweed could work nicely too in winter.

Experimenting is fun and in this case useful for us readers.

Looks like you’ve embraced black jeans now that you have at least two pairs.


Ha, I won’t do that. Style evolves over time, even if the principles (once settled), remain largely unchanged. Associations do vary and we give certain garments another try.

In my case, I find myself more willing to try more structured jackets (heavy ones like tweed, used as outerwear) with casual trousers than I did in the past.


And I think you shouldn’t have changed your mind 😉 Still suits you, though!

Lutyens Brontis

Hi Simon
It’s a good look but to my eye the Sagans look too light, even dinky, with this outfit. A leather loafer would’ve worked better.


I like the whole outfit but I also feel it would look very nice with something like the C&J Boston, maybe in black grain leather rather than the smooth black that they do. This feels more summery and suited to the occasion and weather but if you were going to wear this back in London, Simon, you wouldn’t go for something heavier?


Hi Simon,
Out of curiosity, why did you go for the Levi’s instead of the the Bryceland’s (black) jeans?

Peter Hall

Where do you think texture sits with black,Simon? Would you lean towards a smoother look?

Your shirt gives depth to the outfit. Looking at the outfit ,in the round,I would go for Socks. I might ,daringly match my socks with the tote.

Aaron L

The tote does add a nice dash of colour. It’s a good addition. The socks would be daring.


If I am correct than in the recent articles since a couple of months you have been wearing belt with every jeans of yours whether with or without a jacket.
Is there a shift in thought on jeans looking better without a belt?


Another great post. But it touches on something at the core of my style.
I like to dress well, but I don’t like to stand out. Likewise, I don’t like to look like I’m wearing a “costume”. Case in point, I like the ivy look of the 60s (less the pure mod styling), but I don’t want to look like a pound-shop paul weller, and so consciously don’t wear the Harrington I have with loafers as it’s too much. I identify with both items, but together, it looks like I’m playing dress-up and I feel less comfortable.


This is a good point. I feel the same as a fan of Persol sunglasses avoiding Harringtons to not look like I’m copying Steve Mcqueen. I ended up with a cotton bomber jacket instead


Nice shirt and i like the look overall. Black seems to be an obsession of yours recently – lots of articles around this theme in the last 12 months or so – perhaps enough?. I don’t know if i find it especially showy as such but an all black outfit is somewhat of a statement although not more than than wearing an entire outfit in any other colour i feel, aside form maybe navy. I think its the commitment to a single colour that’s the main point. Two points id like to add – i’m not sure about the bag. Im not a big fan of the monotone look with a ‘pop’ of contrasting colour. I always find this somewhat jarring and a bit ‘obvious’ or crude. Always reminds me of those terrible black and white images of a London street with just the post box coloured red or perhaps a femme-fatale in B&W but with red shoes- barf. Secondly, why the Levi’s over the back Brycelands denim you’ve featured previously?


Really nice Simon, not much else I can say because the outfit speaks for itself.

As far as showy goes, I feel this is on the closer to safe end of showy – everyone knows black looks good, as long as you make it look good (as you do here) IT IS.

One thing is definitely true and that’s just how well everything fits you, that’s important when black is on the agenda I feel.

The new shirt looks beautiful, cheers!


You look “cool” Simon! Kind regards


It’s not showy at all. You took the usual tailoring principles and applied them to something else, and it just works. Lots of people wear black jackets or suits, and you’re way too young for a rockstar. There aren’t many who are below 70, and even then I’d rather be mistaken for one rather than for a navy-uniformed politician.


Hello from New York, where anyone can wear any amount of black at any time. Maybe 10 or 15 years ago, when I was more engrossed in the #menswear culture, I reserved black for ceremonial clothes, funeral ties and shoe leather, but now, things are looser. I personally don’t get as much wear out of my black denim shirt as I do from black voile, which is great in our soupy summers. One caution: best to hand wash black shirts separately, especially at first.


If this is the prototype of the shirts that are meant to replace the PS Everyday Denim: I think you mentioned, that the new ones are made with the intention of being more of a RTW product? Please then consider making the sizing a bit more generous. I think about more space through the chest and arms. If the shirts will be as slim as the current RTW PS oxfords for example, I think a lot of readers like me will be excluded from the offering (and sad). Cheers


Thank you! I forgot to mention the shoulders, but I am sure you got the picture.


I would second the request on sizing and note that the sizing gap between medium and large is too big.

Nicholas Van der vliet

Be yourself, everyone else is taken.
As a much, much older man, I use an old Margaret Howell Howell jacket to achieve a worn in, faded approach to this look. Age gives freedom.


I enjoy the look. All black is understated yet masculine and sexy if kept simple. Fading on denim takes the edge off enough so that pretty much anyone can wear it, especially if they switch the Sagans for some derbies. During mid-summer, for occasions I’d consider this combination, I’d personally keep the jacket off until evening.

I agree with the Jamie who posted earlier about the bag, to me it offers the wrong kind of contrast, maybe if it was darker shade brown. Also as unfortunate as it is, the sunglasses can’t stop reminding me the man of the hour Andrew Tate, a quick google image search will reveal why.


It may be time for an article about black in the ‘things I was wrong about’ series..? There have been a few black items recently.
Back in the days you had quite strong opinions against black, I remember reading things like ‘black is not a color’. I was a bit confused as being an architect it was almost a kind of uniform.
It would be interesting to learn your views now on the color and perhaps have some guidelines as well.

Great combination btw, I geuss it worked especially well in situation that tends to be rather excentric.

John Kiely

Hi Simon,

Looking good. Really works for you.

I get what you mean when you say ‘As big a mistake as any other when you’re first getting into clothes, is trying to look like someone else.’ But doesn’t everyone do that? Isn’t this part of the process of developing your own style and tastes? Perhaps after trying to look like multiple other people, you settle on what actually suits and works for you. More like trial and error, taking bits from a variety of people. This process is a big reason why so many people within this community follow the likes of you and others on Instagram, I believe.

JJ Katz

Is such an outfit REALLY so showy, nowadays?!? I would think roughly 1/3 of males in central London wear some version of this…

Charlie Leerhsen

Enjoyed the article, as usual. I’m a journalist and I often wonder about what to wear while interviewing sources/subjects. I don’t want to be the star of the show or look like put on my Sunday best because I am in awe, but it’s also important to me (in order to signal that I am worthy of a thoughtful response) not to portray the ink-stained wretch. This outfit seems to strike that balance and could very well be a go-to for such occasions. Thanks for the inspiration.

Joe O

This is a super-fine look. The crazy part is not wearing all-black in a variety of textures and dyes, but that you are doing this IN THE SUMMER IN ITALY.


I find bright days to be the best for wearing black, especially if you’re on the paler side. During sunny days, the shadows are deeper and color pops more – contrasts are enhanced, which makes the strong contrast between the outfit and the skin blend in better. On an overcast day, especially in a city with lots of Grey building, the high contrast outfit will stand out a lot more.

John II

This looks out of place in the time and setting (viz., a summer’s day in Florence).


This is actually quite a good look, I wasn’t sure at first but the article won me over. Simon I get the feeling that you could develop this look over the coming months/years. Socks, a tie of some kind, and probably a hat would all the useful to take this look a step further. Something to consider


In love with the shirt! Any idea on timing when you might release it?


Roger that – can’t wait!


I really like the outfit, one I would wear much more easily than any more classic jeans and tweed jacket in places like Hackney. If I am allowed a constructive feedback, I think you spent too many words justifying why you dressed like that rather then “explaining” the outfit (e.g. washed vs black denim, cowboy belt vs alligator etc). It looks cool, own it 🙂


totally makes sense what you did and why. I just think that it could have been more useful for readers that are not used to dress all black to go further into the thinking behind how you chose the ensemble. Then, hey, you probably know your readers better than me!

Eric Michel

I have always been a fan of all black. As mentioned it needs serious attention to cut and fabrics, a bit like minimalism in architecture is all about volume and materials…


I have always liked black clothes, but I also fell in love with clothes in 2004 when I was watching Dior Homme by Hedi Slimane. It feels naturally to me coming from that background to still have some black tailoring, like a black cashmere sports jacket and black jeans. I lived in black skinny jeans, black boots and Leatherjacket for 10 years and played guitar, haha. Even if I then started working at a formal Office and I fell in love with tailoring I think its important to still be yourself and you could be yourself with small subtle things. I dont fel comfortable in loafers and pink shirts for example and Will never do I think…but I love a lot of other classic sartorial pieces. And I will always love boots for the rest of my life…even if I’m not wearing them on a regular basis today when I am over 40.

Sorry for long message. I think a black jacket has its place in the wardrobe. Your dont want to look like your at the Office when youre on a drink on friday night.


I really like this outfit and might take inspiration from it – I wear black casually a lot but have never done all black as a tailored look.

Personally I think this works much better than your attempts to wear black in more subtle ways like your black tweed jacket and olive trousers, which is a good outfit but defeats the purpose of wearing such a powerful colour for me. If you are going to wear black you might as well do it with style and turn it into a ‘look’.

I concur with one of the above comments that the loafers look too dainty for this outfit to my eye. I would have gone with something more rugged and casual like a black chukka boot but that would probably be an outfit that feels like *me*, not like you.


Thank you for another thought-provoking piece, Simon. It’s really impressive that you continue to push your style boundaries when it must have been very easy to settle into a ‘house’ look and use it to reinforce your personal brand.
A few thoughts are racing through my mind upon reading this piece and the always-fascinating comments…
Firstly, I feel there is a fair degree of ‘overthinking it’ going on. It’s incredible how many people, including yourself, say things like “I wouldn’t want to look like…”, or “I wouldn’t want anyone to think I was trying to…”.
The overwhelming majority of people know so little about style and how to/how not to dress that the only thought they are likely to have upon seeing someone in any kind of tailored jacket is how smart they are. I guarantee they are not thinking about whether the texture passes muster or how an all-black look might be perceived as unconventional.
I suspect what people really mean is they are worried about how menswear experts might judge them and that strikes me as very a negative way to frame personal style choices – be yourself, people, and make no apologies to anyone, including Simon, for your choices! Contrast socks may not be for Mr Crompton; they might just be perfect for you.
And I mean no disrespect here at all, Simon, I am simply emphasising a point.
Secondly, black can clearly look very sophisticated and there is much to be said for a minimalist aesthetic. My personal view, however (and I have worn plenty of black down the years) is that it is a tough look to pull off.
Black can make people, especially those with very pale skin and men who don’t typically wear make up as women or rock stars might, look very washed out. Black clothing can also be difficult to keep at the right shade of black because jeans, shirting and polos/T-shirts can fade very quickly upon washing – this may be the desired look for some, but otherwise will prefer a more pure black.
Finally, I think the contrasting bag is spot-on, Simon, and particularly for Tuscany. I was in Florence earlier this year and noted how well the locals paired black and colours in the tan/camel/beige spectrum so effortlessly. Of course, the quality of the local light has a part to play as others have indicated, but my main takeaway was that it worked because they had dared to try it, rather than any magic formula tied to a particular place and time. I would love to see a piece on how to really make that combination work (apologies if I have missed one) as it would be a warm weather/better lighting equivalent of your pieces on the cold-colour capsule, which have certainly inspired me during the darker months in the UK.

Cormac Lynch

To my eyes, it doesn’t seem showy. If ‘all black’ is a statement, then the different textures, especially denim, do a great job of toning it down. My only point of contention, albeit only an opinion, would be the the shoes. They are loud. With more subtle shoes, even (not smart) black derby or boots might, it might have been more harmonious. What do you think, Simon?
Great article, as always. I love the weekly dose of style experimentations. Thank you.


Hi Simon,
Yes, for an evening event, it would be fine indeed. However, even on such occasion, I think the look could be effective by making it a little bit more substantial and by the same token more cohesive. You could then swap the following two pieces: the jeans for your black cords from Pommella and the Sagans for EG black belgravia.
I hope it makes sense to you.


Ps. I mean the black suede belgravia.

Tim J

Hi Simon,
Enjoyed the article as always. Nothing unusual with wearing black when you’ve grown up in Melbourne (or Paris I suspect). You mentioned you were working on a prototype shirt with the faded black denim. Are you thinking of making available a finished shirt, the fabric or both? Just curious because I’d be keen to have a shirt made from the fabric if you were planning to sell lengths of the fabric.


Hello Simon
It is interesting that you talk about what feels right at a certain point in your life, a place, or an event where you are.
I too noticed that my own perception of what I feel I can wear has changed over time and my wardrobe looks quite different now from what it looked like five or even only two years ago.
Black and neutral colours are especially interesting for me now and I am reading your articles on those topics with great interest.

The one problem, however, I have with an all black outfit is the combination of different shades of black.
Different shades of black or black in different stages of wear are no problem when they are separated by a different colour.
Say Espadrilles in a black cotton and a black polo shirt worn with cream linen trousers but if you would wear black trousers with that you would wear three different kinds of black in one outfit.
Your jacket/shirt combination in the pictures is a good example. I feel that the different shades clash and for me this unsettles the whole outfit.
Something I noticed time and again and I think will not change in my perception of what I can and cannot wear.  


Interesting article Simon, not least of which because I find myself wearing a similar outfit on occasion – just all navy (as you mention in one of the paras, it’s easier!)
Dark indigo denim jeans (if anyone is interested in a high rise with a fuller leg, I can thoroughly recommend, an old navy linen shirt that’s faded and washed out, and navy blazer. The only colour concession is black suede loafers (wonderfully versatile), or, oddly, the green suede loafers I stupidly purchased on a whim years ago and have not been able to pair with anything else.
Not being all black I find it avoids the “ageing wannabe rock star” connotations, and is demonstrably different without being too far out of my comfort zone of flannels or chinos and sports coat.


To the folks suggesting that black for summer is inappropriate, this look would fit in perfectly well on a Los Angeles afternoon. I’ve been wearing a lot more black myself recently – tending towards tonal white and tonal black casual outfits – and the color matters much less than the weight and construction in terms of heat. It can also draw the eye through contrast, a strong look without the dandy associations of white


I agree that “no black outside of tuxedos and funerals” is an online menswear rule that needs to be scrapped.
Next up: that black shoes are “too boring” to be worn with charcoal, grey or navy (yes, navy) suits compared to brown or burgundy shoes. This has NEVER made sense to me, yet this idea is so firmly engrained in some places.

James G

The shirt is georgeous. Hope to see it available in the future.

As for the choice of footwear, the Sagan’s strike the right balance between effortless, sporty and elegant, while the color adds a bit of edge and even power.

A successful departure!


Agreed re: shirt!


Hi Simon,
I’m after some washed blue jeans and have been considering some Levis from the Levis Vintage collection, although judging by the reviews on their website they aren’t as favourable.
Are your black pair true vintage in the sense of preowned or from the vintage collection? Are they a 501 and how do you find them in comparison to Blackhorse Lane?


Thank you Simon. How is the quality of the jean, in the context of it being vintage?
Only I’ve had some Levis in the past, non-vintage brand new, and they were forever needing repairs. So not the best experience with that manufacturer (regular line, not LVC btw).


Excellent, thanks SImon


Love the japanese reticule!

Rupesh Bhindi

Hi Simon,
Please could you advise when consumers can expect the black washed denim fabric on PS website?




Hi Simon, do you find the alligator as casual as a woven belt? I’ve seen you sucessfully wear this black Rubato alligator belt in casual attire though I would have thought it to be more formal. I am looking for a black belt to pair with a more casual black loafer and have had my eye on the Rubato black woven belt as the natural choice though sold out in my size. Trying to hold out for that or perhaps try the alligator option if just as versatile (the Berg & Berg offering as the Rubato is no longer sold). Thank you, Andrew


Hi Simon

Thanks for another article. If this crossed your mind, found you share why did you decide for hopsack instead of linen for the jacket? I would imagine that for a “look”, the wrinkles that a heavier linen would get would be closer to the “cool looking” idea of the ensemble



Thanks Simon – I think the monochrome black suits you. Perhaps one of the important details of dressing in a single colour is that the colours and textiles are slightly different as you’ve done here and as Andre Larnyoh’s ‘Outfit 4: Mismatched navy’ (, and that the mismatching gives the outfit a little depth and complexity.
Couple of questions for you: are the Levis 501s, 505s or something else? And did you have them altered and if so how (particularly interested in width of the trouser leg as I’m struggling to find something that hangs as well as yours look.)
Also, when you have any available time, I would be very interested if you might explore juxtaposition. Juxtaposition seems to be a magic key to great style but really hard to pull off and I raise it because I stumbled across an article on Drake’s Michael Hill called ‘Michael Hill’s Menswear 10 Commandments’ and point 5 reads “David Hockney taught us: Better juxtaposed than matched.” ( – would love to see a feature on this.

<<Simon if you can include the image of Hockney from that article that would be great – can’t quite figure out how to upload an image>>


Yeah, you don’t have a band but nicely done the same! Exploring new outfits it’s something I’m doing more and more too. Like to walk on a side path before to enter again the main road. If I can (can I?) I would have worn a slim jean (or a skin one) and a two tones moccasin, just to spicy up the outfit with some white.


It’s in someway a “coded outfit” (plenty under rock fashion or YSL hashtags), and the “out for a dinner” one for the rocker. You have already moved from your confort zone, never say never!

Daniel Francis

Hi Simon

I like the idea of an all black outfit especially the black jacket. I have two myself, one of which one looks like my old school blazer. For my personal style I would swap the loafers for black trainers eg Common Projects and wear black socks as I’m not a sockless type of chap and that would do it for me.

As another variation I would swap out the denim shirt for a crew neck sweatshirt in a lighter colour, maybe sky blue, to provide a contrast against the black.


I like it. I don’t think it’s showy at all, as a matter of fact, I might have added a scarf.


This outfit looks great and isn’t too showy at all – certainly no more showy than wearing a suit casually nowadays. I like it.


What is your opinion on black linen or cotton shirts?


Not a bad look by any means, but I feel like it expects of the wearer that precise attitude of a rockstar, given its association with them which you also alluded to. Especially with sunglasses on.
Of course, most rockstars don’t wear bespoke or even particularly high quality tailoring, so that’s a distinctive difference, but only to the trained eye (very few people) and even then it gets harder to tell at a glance or from a distance when it’s all black.

Rupesh Bhindi

Hi Simon, when do you expect the black denim shirt to be available on PS website? Also where did you purchase the black washed Levis jeans from?


I have a black crew neck sweater which I wear on it’s own with olive green chinos and dark brown suede loafers.
I have heard a lot of people saying black and brown doesn’t go together and therefore wanted to understand whether this combination sounds good or should I wear black loafers with it?


Hi Simon, I really love the sunglasses. I also wear sunglasses very often especially by Serengeti’s and maui jim’s. What did you wear in this photo? And what colour?


I recommend to check out serengeti eyewear. I think you’re gonna love lots of sunglasses by them


Hi Simon. Will this black denim shirt see the light of day this year as a product?


I am a big fan of all black look. I am thinking about all black fresco suit (something I would wear at evening of course, it’s too hot where I live anyway) not sure about the shirt fabric though. Any recommendation? Linen perhaps? Or something cotton?


Cream silk? I see, and how about cream linen shirt or perhaps black linen shirt paired with a black fresco suit? And yeah natural coloured linen could work. Thank you.


Thank you, I am sure I’ll be able to pull it off Simon


I was re-reading this article. It’s a great piece of writing; how you contextualise the outfit and talk about how you feel – not just a description of the clothes.