How I wear a black leather jacket

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I’ve had this vintage leather jacket for about four years and it hasn’t been worn often - perhaps a handful of times a year. 

If I’m honest, it was because I felt a little self-conscious in it. I didn’t want to look like I was pretending to be a biker, or going through some kind of mid-life crisis. 

That might seem silly, but as we’ve discussed in the past, a lot of what people think of as style is about the associations we have with clothes - the people, the places, eras, ages, attitudes. 

And if any piece of clothing feels risky in that way - feels like something a guy wants to wear, but might say he can’t ‘pull off’, it’s a black leather jacket. 

Perhaps a better way to put it is to say that I wasn’t sure the jacket was ‘me’. 

The reason an old, bald guy in an open-top sports car might traditionally come in for ridicule is it can look as if he’s trying to be something he’s not. 

Trying too hard is a style-killer generally, but it’s particularly bad when trying to be someone much younger. (Because, of course, it’s something a lot of people identify with.) 

So was the jacket ‘me’? Well, bear in mind that my main aim with clothing remains to look well dressed without standing out. It’s what feels most comfortable for me, and gives me most pleasure. 

A black leather jacket is riskier in that regard, and that was what I was afraid of.

But, over the past year I’ve come to think that this horsehide jacket - aged and styled as it is, and worn in this manner - is something I’m comfortable in, and now enjoy wearing immensely. 

The most important thing, I think, is that it’s vintage. 

The jacket already looks like an old favourite, rather than something bright or flash. It looks like I could already have owned it a long time - become part of me - even if I haven’t. 

This is often the problem with cheaper leather jackets. Because they are often plastic, or plastic-coated, they never age well. It looks wrong - like jeans that don't age because they're full of elastane.

The fact it’s old also means it is literally less flashy. The leather is dull, not shiny, and so is the hardware. 

Second most important is the styling. 

The simple turn-down collar and three pockets is the simplest style you’ll find - there aren’t even pleats in the back, or contrast stitching. Just a sewn-on half belt and two adjusters. 

I love the fact that the label describes it as sportswear. This is not a flight jacket or a bike jacket or anything else functionally specific. It's just for being, generally, active. 

That label also identifies it as being from M Bogen & Co in Lowell, Massachusetts. I can find references online to staff at such a shop in 1950s, but if anyone else knows anything about them, please do let me know. 

Then there’s how it’s worn. Not with a white T-shirt and blue jeans, let alone a bandana and biker boots. 

I like a charcoal knit underneath, like the old Drake’s lambswool one here; and pale beige chinos, from The Real McCoy’s. Both are suitably understated, while still being, of course, wonderful pieces of clothing.

The boots are the Cranleigh from Edward Green I wear a lot, in mink-brown suede. The storm welt and split toe give them enough ruggedness, and I prefer this to either a Galway in the same material (smarter) or a work boot like my Viberg (more casual/chunky). 

A grey sweatshirt underneath is also great, as are darker chinos or really dark denim. Both pretty easy and obvious combinations. 

The only unusual style I’ve found I like is wearing the jacket with charcoal flannel trousers, the same boots, and a casual shirt like denim or chambray. It’s a pleasing mix of tailoring and workwear. 

The jacket is from RRL in New York, again bought several years ago. 

As with most vintage they carry, it was expensive but perfect. Great size (only the arms are a touch short on me), great condition, and great details. Beautifully worn in but nowhere worn out; original hardware but still functioning perfectly; fantastic original blanket lining. 

The only change I made to it was to replace the moleskin-like sleeve lining with a synthetic. The former was nothing special, just warmer, and a real barrier to getting the jacket on and off easily. 

When Sarah and Pauline at Cromford examined the jacket, they of course pored all over it - appreciating old leather as only leather specialists can. But they particularly picked up on the way the front panels have aged. 

The panel on my right, below, is a lot smoother than the one on the left, which is more wrinkled. For Pauline, this showed its age. No modern jacket would be made with such different parts of horsehide, as customers would complain it was a mistake. I love the difference. 

When we were running the pop-up shop in The Service recently, two young guys came in on different days, both wearing black Perfecto jackets (or imitations of). 

They both looked great. But they were young, skinny, tall, good looking, and had some swagger to match. 

The jackets suited them, worn like that, at that point in their life. I will not say that no one older or larger or more timid couldn’t look great in a Perfecto. I’m sure they could. But at the same time, I suspect those guys won’t dress like that when they’re 40. 

There’s no need, really, to unpack the reasons why. The only thing that matters is that those jackets looked very ‘them’ and this old horsehide feels very me. And that’s as important as anything when it comes to dressing well.

Photography: Mohan Singh @mohansinghphoto

Hat: Red PS Watch Cap

Above, pictured chatting to reader Andrew, during his shoot

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Sean

Simon, Simon
I don’t think this suits you at all.
I think you should add this to the items you’re selling in the pop-up today.
But not until about 12pm, as I can’t get there before then.

(PS; very enjoyable article for someone like me who’s often wondered about a black leather jacket. Maybe I’ll start hunting for a vintage one. Thanks)

Black

On the contrary, I think it rather suits him. Haven’t you heard!? Black is the new Black and it is back, baby!

Stanley

well, i think this leather jacket bring me the flesh Simon that i never seen before. I like this style a lot

James

Hi Simon, could i ask how much the jacket cost? Also if you don’t mind me prying how old you are? I don’t think age comes into it so much in terms of wearing a leather jacket . More important is the person themselves. I can think of many aged musicians who i would not think look out of place in a leather jacket at the age of 60 or 70. The young guys you refer to in the article could well continue to wear a leather jacket and pull it off all their life, you never know.

James

Wowee £1500, you really no how to treat yourself. I am assuming it was a spur of the moment purchase as you cant have expected to have found it? Commiserations on the big 4-0.

zo

I think the jacket looks great, and you look quite comfortable in it. And I agree it’s more about your attitude/personality than your actual age. Allesandro Squarzi with his greying hair is pictured regularly in a Perfecto. So do a lot of middle-aged Japanese style bloggers, who combine it with tailoring. They all look great IMO.
On that subject…sometimes, I do wish I could wear my 2-year old’s dinosaur rain coat or his teddy bear jumper without anyone batting an eye…alas!

zo

You’re no less a superstar Simon, don’t let anyone else tell you otherwise.

Ian A

Yes I’m much happier at 47! Personally i won’t replace any of my 2 brown and one navy leather jackets and will only think of replacing them with suede as i allow my wardrobe to naturally narrow down over time to a handful of critical pieces.

Steve B

Good for you Simon; you’re as old as you feel & like god ‘old’ favourite, or vintage clothes, you grow to appreciate the quality that comes with age. Just keep as fit & healthy as you can to drape those clothes. Ditto for 50…

Simon C (not Crompton)

I used to wear a lot of black until someone commented that due to my pale complexion black made me look like Nosferatu! I no longer wear black.

Karol

I had similiar ideas, but for different reasons – I’m not interested in doing the metalhead look I wore when I was a teenager. The solution seems to be pairing black leather with vaguely rugged Ivy, casual Drake’s-like pieces. Chinos, corduroys, workshirts, rugby shirts, some knitwear… I don’t think it’s that hard, it’s just that plenty of men try to wear the whole look they saw on instagram or pinterest, and it looks really insincere.

Simon C (not Crompton)

Thanks for the comments Karol and Simon. Time to re-think black as part of my wardrobe.

Burt

This entire article almost reads as a justification for why you are wearing a leather jacket. That’s a shame and not necessary. Since you’re such a classic face / physique and not a rowdy guy either, no one will suspect you of trying to impersonate a biker, rocker or old guy trying to look younger. It’s precisely because you’re playing with these ingrained beliefs that it can work. Suitable accessories as beautiful glasses will enhance the contrast. It is playing with the signal value of garments – and what we put in them ourselves. I would combine this jacket with a nice scarf or bandana because of your high neck line (a high knitted collar would suit you too). And of course also with a nice pair of high rise dark blue jeans or beautiful flannels rather than white or cream trousers. The next day you wear your suit from Chittleborough & Morgan, all like it’s the most normal thing in the world. Because that’s what it is 🙂

Henry

I think tailoring, especially long coats, suit you far better than this example!
I have a similar build, around 6”1 and 80kg and have tried incorporating short jackets into my wardrobe however it simply doesn’t look as good as something long and sweeping.
Furthermore, I think black outerwear such as this jacket is rather graceless, there is no need for this if one can speak of a wardrobe full of bespoke.
I might dare to suggest, most of the readership agrees that tailoring is de rigueur for a man of standing in the city.

James

Thanks Simon. I think your last point is really important – the outfit does seem to contrast a little with the classicism of the RCA in the background, and I imagine would look much more at home in casual surroundings.

Steve B

It seems some people like to consider themselves important in their clothing, to always stand out, whereas sometimes you want to blend in like a chameleon. Tailoring is not always appropriate to make you feel comfortable in a crowd. Wearing this jacket at a gig, say Brixton Academy would look good, perhaps not at the Royal Opera House in the stalls ( although I’d not dictate to another ), but tailoring might only feel completely comfortable at the ROH.

Andrew

Hi Simon, having seen you in the jacket on the day of our shoot, I am surprised to read it look you some time to get comfortable with it. I thought it looked really good on you and totally natural. Unfortunately, the photos don’t do full justice to the texture of the leather, which is really nice when you see it up close and feel it. All the best, Andrew

Walter Sickinger

I am an old (74) bald guy with an open top sports car ( a1987 Porsche cabriolet which I purchased in 1987 upon turning 40) My style icons have always been the British actors of my youth in the 60s/70s such as Caine and Connery. I was and still am a fan of their tailors Anthony Sinclair and Douglas Hayward and any tailoring I have made to this day reflects their style. I have always resisted buying a black leather jacket for the reasons you mention but your article may be the tipping point

Andrew Poupart

As another old, bald guy who rides around in a convertible, I’ll add that there are two ways to avoid looking like you’re having a mid-life crisis. One, be clearly of an age well past mid life. Well, I qualify there. Two, drive an old car. Like my 1975 450SL. Having said that, a black leather jacket is something I have always felt is not “me”. But it looks good on you, Simon, and I’ve glad you’ve become comfortable with it. That’s the key.

Peter O

I’m always especially surprised by you guys with less hair that you apparently don’t protect your heads with a cap or hat.

Steve B

Protect against what; falling masonry? If you mean the sun then maybe yes but that might be true of most men in intense sunlight if they want to avoid skin cancer. As for the cold, again this might apply to all unless you like a cold head. Or do you mean that bald men should somehow be shamed? Sheep have a lot of wool but not much sense it would seem here with such a comment.

Stephen

Hi Simon,
It’s great jacket and it looks very good on you.
I once read about some research and experiments on how we see ourselves in certain clothes and how others view us. I wont go into it in detail, but suffice to say the experiment quoted used quite an extreme example (bright gaudy tee I think). Those wearing them were surveyed as highly self conscious ; in a complimentary survey the amount of people that really noticed those in the tee’s was surprisingly low. The article may have been in Die Workwear.
Bottom line for me is don’t over think it and enjoy your style!

Jim

Nice line!

Aaron

A brilliant piece Simon,
As someone working in a field where most of the actual clothes you discuss would be taken as trying too hard (biology research), this 40 year old bald man has learned a ton about how to creep up on his own style in midlife. This article perfectly highlights walking the line, with clear principles that one can employ in their own decision making.
Can’t thank you enough for your work – your articles have become a dose of thoughful inspiration in my regular life. Just wonderful.

Peter Hall

Just out of interest, if you had the opportunity to buy the same jacket in brown would you have taken it?

zo

black leather > brown leather any day!

Craig

Great looking jacket.

Some jackets are easier to pull off than others. The double rider biker jacket with a ton of shiny metal straps, buckles and zippers will look weird on most people in most situations. It carries a lot of connotations, and unless you’re a biker or someone about to play lead guitar in a rock band, it’s a bit much. Like safari jackets, they just seem a bit too much like a costume for me to be worn in regular life – even if you ride a motorcycle on the weekend. They also tend to be uncomfortable and snug, which is the opposite of stylish to me.

But a more sedate jacket, with a looser fit and one lacking all the shiny bits, are no problem. A thinner leather also helps the jacket, and wearer, look more relaxed. It’s easier to wear the jacket, and not have the jacket wear you.

RTK

I am now a regular buyer and wearer of 2nd hand clothes. They can be purchased in charity and thrift stores for pennies on the dollar and you can find fabrics and construction that are often far superior to very expensive new garments. However I do not think this horsehide jacket meets those criteria. While it is over 60 years old it is of mediocre quality with mismatched skins and a worn lining at a price of $2,000 USD! This does not seem to me to be a good value. But again I can’t understand how someone could pay $500 for a worn out pair of blue jeans and then spend hundreds of dollars repairing them. Just the thoughts of an old man approaching 70.

Oggi

Like the jacket Simon.I wear a dark brown cafe racer leather jacket with slim navy corduroy trousers,dark grey flannels or navy raw denim jeansAge wouldn’t be my concern wearing this type of jacket it’s really about how you feel and how you look in this outfit.

M

That jacket suits you just fine Simon, it’s not amazing but you don’t stand out in a negative way. Obviously you have to respect time and place with an item like this but for running errands it works.
Here in the former Soviet Union everyone can wear a leather jacket and not look out of place. I don’t feel like same kind of associations exist here. Though depending on how you carry yourself you might be mistaken to be part of the criminal underworld
I personally have owned 4 leather jacket and I have never had an “attidude”. It’s just a standard piece of outerwear.
Obviously cafe racer with beer belly isn’t ideal but dress for your body and age and you’re fine. M65 style works great for 40+.
That being said I don’t ever see myself owning a leather jacket again. I feel wool/cotton is just more comfortable and better fitting/feeling.

Ondrej

Frankly, I am quite surprised, that nobody mentioned Lowell, Massachusetts also as birthplace of Jack Kerouac, especially in connection with this kind of garment.

Eugene

As somene a little older that you with only slightly more hair, but similar light complexion, I don’t wear black at all. I find it washes me out, whether a leather jacket or anything else. I love shades of brown or navy for jackets – as bland as that may sound. This is a nice jacket, but I think it would look better on you and with your other clothes in dark brown.
With regard to mismatched panels, there are a few makers who do that new. Fine Creek Leather Shinki horsehide jackets (out of Japan) is the primary one I can think of.

CDBP

great points Eugene

Toby Mott

Simon the jacket looks great and more importantly you like it despite being aware of its possible drawbacks, and with those in mind would you ever consider wearing leather trousers?

Emerging Genius

It needs to be worn with the right attitude. It’s that straightforward. I am of that “alleged age” where it seems try-hard.

A female cop at Washington National Airport approached me and growled at me.

If it’s worn with hesitation or lack of sekf confidence then it’s not for you at any age.

That goes for bespoke as well etc

Chris

Do you prefer brown or black leather jackets? Do you think one color is more versatile over the other?

Jake

That is a lovely jacket, Simon. Speaking as a middle-aged man who also owns and still wears a vintage leather jacket, I think yours looks good and you wear it well.

Mine is at least 25 years old and I’ve had it since I was a teenager. It’s more an M65 style and fits in well with my lifestyle now however the suggestion to wear it with flannels never occurred to me! I’ll have to try an outfit with my charcoal flannels next time. Thank you for the inspiration.

Noel

I think you hit the nail in the head Simon when you say that style is about the associations we have with clothes.
I look at these pictures and the jacket works well with this outfit. Yet I can’t escape the associations of black leather with bikers or rock stars. If I had such a jacket those associations would be at the back of my mind, making me less likely to wear it. Dark brown works equally well and escapes these connotations for me.

Yosef777

Beautiful jacket but too many associations of fonzie/happy days and James dean not too mention Iron Maiden for me. Even with the tailored trousers, fine knit wear it seems contrived. Unfortunately even aged rock stars look silly in them. Better off in a Barbour/Belstaff race master once you are at a certain age, sorry.

jack

It is interesting that the jacket may originally come from Lowell, Massachusetts. Lowell is one of the great mill cities of the world, now much of it is a National Park. Very beautiful architecture and urban design. Yet sadly, associated with urban decay. Its sister city Lawrence is even more an example of urban blight. While Jack Kerouac did come from Lowell, he was more of a white T shirt and short sleeved shirt image. Definitely a working class person; about as far from Permanent Style as possible! (Although he did wear a coat and tie for public appearances.) I believe the image we are all looking for is Marlon Brando in the movie “The Wild One.” (1953) A biker in a biker jacket and an image that is indelibly etched into modern culture as most rebellious and threatening. We can not escape these iconic images – even with a leather jacket like yours, Simon, that has far less zippers and metal. One of the constant threads on this blog, is the difficulty of escaping the tight grasp of the past with the use of such words as “costumy” or “for old bald men” or “feeling insecure.” And of course fashion, as opposed to style, has every thing to do with imagery. I would commend you, Simon, on pushing these boundaries, exploring clothing that does conjure up cultural associations. It is one on of the ways you combat the other end of the spectrum – conservatism. You are trying to walk a fine line between conservatism and exploration and experimentation – this is the strength of Permanentstyle. Keep at it.

Noel

Maintenance must be particularly important for vintage jackets such as this one. How does one keep the leather supple? Do you condition it in a similar way to leather shoes? (As far as I know this topic has only been broached in respect to suede jackets)

Russ

Phew. Thank goodness it hasn’t got any studs nor more zips, Simon.

And even without them, I’d be careful
about leaving that red hat hanging out of your left pocket (which an old uni friend from our alma mater and so inclined told me is a secret sign).

Chris

It’s a strange thing isn’t it. If the jacket were suede in black, brown or tan we wouldn’t give it a second thought but black leather comes with a lot of baggage. For me you can wear one if it comes with no and I mean no embellishments and you don’t add any like the aforementioned bandana. Also importantly, and this is were I fall down, you have to be slim. Tight leather is very unforgiving!
But it’s a balancing act. Yours looks great but turn the collar up and it’s Fonz territory.

Anonymous

Hi Simon,
What are your thoughts on the leather jacket from Stoffa? I believe they offer it in traditional colors (black and brown) as well as navy.

Tony H

It’s interesting which things we approach with trepidation.

There are plenty of people out there who feel wildly out of place and uncomfortably costumey in a suit, too.

I bought a five zip for the first time in the second half of my thirties – something I never would have done in my twenties – and I love it. I find you make it work with almost anything as long as you have a jumper on underneath.

Naveen Kumar

Hi Simon,

Straight question

Should we worry about matching the leather, I mean when you have worn black leather jacket with dark brown shoes ? Is it sartorially right ? Or it again comes down to personal choice and confidence of the wearer ?

Naveen

Tom Higgins

Well Simon, I think the jacket looks great on you. And the various ways that you describe wearing it sound good as well (the tailored flannel trousers, etc.). I am a lot older than you (although remarkably boyish for my age…) and I have a leather bomber jacket (elasticated waist and cuffs) from MacDouglas that I bought about ten years ago (when there were at least traces of boyishness remaining). In all truth, I suppose I have to say that it’s ageing better than I am, but I’m reluctant to wear it now, though it occasionally gets an evening outing (darkness helps). I wear it with black tailored trousers, mostly . Maybe I get away with it, maybe not. But I think a style pf leather jacket that can be worn by older men is a buttoned Harrington. Loewe do a very beautiful one; Burberry also use the style sometimes. The fact that they button, rather than zip, gives an air of seriousness that goes better with being older. You know, the zips are for fast removal, I suppose: Older men don’t need that so much. Thanks for the always thoughtful blog. I’d come to the pop-up shops, but I’m stuck in France, where I live, and bloody COVID-19 continues to complicate things.

Chris

I really like it. It tests your boundaries and looks more natural than a suit right now.

Mark

Hi Simon,
As someone older than you who thought long and hard before buying a black leather jacket, I am interested in your thoughts behind it. I agree strongly with avoiding the white tee and bandana and generally toning it down.
I wound up with a similar jacket, the Imperial, by Dave Himel, MTO.
Unfortunately, one of the things that I have learned by following your advice is the importance of fit. Your choice of high contrast trousers in the photos suggests to me that your vintage jacket is generally an inch shorter not only in the arms but also in the body for your torso. I think a better choice given the cost of the vintage piece would have been to get one made for you to more ideal proportions and break it in by working in it in bad weather. The patina will come but the fit will never improve.
This is a small point and honestly one that few people would ever notice in real life. Sometimes we obsess over static photos when we should be getting on with life and breaking in our jackets!

chris k

Nice one Simon,

I’m sure you’ll recall I asked about the jacket in question a few months back on a separate post. I kept seeing this mysterious beauty hovering in the background of your videos. Needless to say, you look wicked. More than do it justice as far as I’m concerned.

I think your comment about footwear is key, with the Cranleigh being just refined enough, it really does seem like a very useful boot. Helps that I like split toes I suppose. I wear a brown A2 style sheepskin bomber, and honestly I don’t think I even like it with rough out suede, just seems a bit of a heavy look, might just be in my head but regular suede seems better. Slim sneakers, casual suede loafers OR a refined suede boot like the Cranleigh, which is exactly why I’m currently saving up for a pair .

Your reference to that more unusual of combinations, flannels, denim/chambray and this jacket is a great one. I really like this look. It never seems to look too forced on anyone I see it on, and seems fresh and modern, yet classic. A nice option other than denim/work wear chinos. Also, there is something about the overall texture of a leather jacket against flannel/tweed with suede on the feet. It really is a cool one.

Lastly, you’re spot on about wearing an aged leather jacket. I’ve found it’s not simply about the texture of the jacket, but actually how much softer aged leather is, they just seem to drape much better, heavier jackets perhaps even more so, like this horse hide, a thicker cowhide or sheepskin etc. I suppose a good leather jacket is similar to raw denim in that sense? Except they require even more break in time, I know mine feels like that, still feel a bit like it’s wearing me, but I know it fits well so i’ll stick with it. Even vintage pieces had to start somewhere I suppose.

BC

Wouldn’t black footwear pair better with the jacket? Otherwise it looks great.

MBB355

It’s surprisingly difficult to find a good black leather jacket. I see you don’t like the Stoffa one. How about this one from Theory?

https://www.theory.com/morvek-l/F0170411.html

CDBP

Please take my comments in the generous spirit in which they are intended.
1) If you are over-thinking a black leather jacket and wearing it four times a year, you probably should not own one.
2) Wear it more. Don’t think about it so much. Unless you wear jeans, or other older beat up trousers ( like heavy, no crease, worn out khakis, with baggy knees or similar ) it may still not be the right thing for you.
3) Use it for utilitarian purposes : fixing a bike, clearing the gutters, gardening, walking the dog or what have you.
My bias is that this thing is maybe just not you and you should stick to brown suede.

John

I actually picked up a similar jacket from Aero few weeks back. It’s the Highwayman model. It’s quite similar, but with a subtle but important upgrade: there’s a nice double seam around the bottom of the jacket that makes it feel more well balanced somehow. They regularly offer used Highwayman jackets for sale so give them a shot, I’m very happy I did.

Jose

Great Article, Simon! Which got me thinking, what style of leather jacket (and color) would you recommend for middle-aged men that it’s age appropriate and stylish for winter. Thank you!

Richard

Hello Simon, Do you have a preference between the Edward Green Cranleigh and Galway in brown suede?
Thank you,
Richard

Richard

I appreciate that feedback. Which would you prefer with nice denim or odd trousers with a sport coat? It sounds like the Galway may be slightly more versatile,being a suede brown boot, easier to dress down?
Thank you

lustigear

I found it quiet interesting, hopefully you will keep posting such type of nice blogs. Keep sharing. thanks.

Larry D.

Dear Simon,
So thankfull of this space and community you’ve created, have been reading and discovering manically these last few months, your articles and comments of everyone here alike. This is my first comment.
I’m in love with this jacket, the whole look in fact. Which of the three jackets I’ve found would you say is more similar to this? The Himel Bros Frobisher, the Himel Bros Imperial or the The Real McCoy’s Nelson? Another you’d recommend maybe? I live in Europe and am a little hesitant ordering something of such a value from Canada without the possibility to return, but from what I understand they are really good at what they do and a few of your readers have had some experience with them (?). How many years would it take for a new quality horsehide jacket to age like this with regular use (2-3 wears per week)? Something like twenty years?
I usually dress quite casually, mostly chinos, shirts, knitwear and trainers (like Spalwart Marathon) being my go to uniform. But have recently been adding a few smarter pieces to my wardrobe (smarter chinos, derbies, outerwear etc.). I love these off white chinos you’re wearing and was thinking of trying the new Rubato cream jeans that just came out. Apart from boots, do you think they could work with black or grey trainers or maybe black derbies?
Thank you again.

Larry D.

Thank you for getting back to me Simon.