Alessandro Squarzi has a reputation as a good dresser, and usually looks appealingly stylish yet relaxed. 

Yet the way he currently dresses is actually very straightforward, and I think can be a lesson to guys everywhere – in how to keep things simple, develop a capsule of high-quality pieces that reflects your personality, and play around largely at the edges, with outerwear, jewellery and accessories. 

Alessandro and I have talked a few times over the years about this, but only briefly. And as often seems to be the case, I’ve never talked on PS about his style, despite how much it has influenced my off-duty clothing. 

So for the latest in our ‘How to dress like‘ series, I talked to Alessandro again, and thought more systematically about his wardrobe. 



1. On the bottom – blue or white jeans 

Alessandro nearly always wears mid-blue or white jeans. “Although I’ve changed in my physical appearance over the years, I haven’t really changed my style,” he says. “It is clear that I prefer to wear five-pocket denim pants or white jeans and over I choose between coats, jackets, leather jackets and sweatshirts.”

Mid-blue jeans, of course, are the most versatile of all casual trousers, and pretty ubiquitous. But at the same time, they’re something you can refine and have a deep love of, as Alessandro does. Once you appreciate the beauty of blue denim, a good pair never looks the same as another. It’s a subtle beauty, like the best PS ones.

White jeans are then the slightly more unusual, perhaps a slightly more fashion alternative. Certainly less common. 



2. On top – T-shirts and chambray shirts

On the top it’s nearly always a white T-shirt, which is easy, universal, and as a colour flatters most people (though it does look particularly nice if you always have a tan).

Worn with the blue jeans, it’s everyman. Worn with white jeans (perhaps separated by a belt or at least under another layer) it’s more of a look. Alessandro swaps between both. 

Then there’s a chambray workshirt. Worn over the top of the T-shirt, or worn on its own in summer, in an easy style and the pale blue that goes with everything.



3. With navy, grey, olive layers

Alessandro likes to layer. “I always try to mix something vintage to my outfits and I really like to make layers overlap and play with them. For example, I might wear a T-shirt with an alpaca cardigan, over a beautiful shirt or a US Navy service shirt and that over a jacket.”

Because the bases above are so versatile, almost anything works over the top. But still the outer layers are mostly from a narrow range: navy knits, grey sweats, blue denim and olive drab. 



4. And either suede loafers or canvas trainers

The footwear is pretty consistent as well: suede loafers (usually Edward Green) or canvas trainers (usually Mr Fliks). Both very easy relaxed styles.  

I think the way Alessandro wears his loafers, actually, is a good example of how much they can dress up an outfit – as we talked about previously

“I have an archive of six thousand vintage garments, yet in the end I always fall back on the same things,” he says. “Probably because you get to a maturity for which you do things for yourself and no longer for others.”

Throughout our interview, by the way, the language barrier stood in the way of specific, example-driven responses, and extended discussions. But hopefully the comments give a decent idea of the attitude.



5. Make it personal with jewellery and accessories

Jewellery and other accessories make this core wardrobe more personal. Alessandro wears a lot of silver-turqoise jewellery and other bracelets, and of course has visible tattoos. 

You don’t have to like either, though, to appreciate the principle of expressing yourself in this kind of area. It might simply be your choice of watch, or one piece of jewellery that means a lot, but it’s effective, less showy for being often hidden, and can be swapped or taken off between one outfit and another. 

I particularly like the way Alessandro wears dress watches like his Patek golden ellipse with the denim elsewhere. It has the same effect as the loafers of adding a a finer, smarter element.



6. And experiment around the edges

I remembered Alessandro wearing quite a lot of unusual pieces – cowboy hats, bright-red parkas – but looking through the imagery, these are rare and usually worn with the versatile capsule set out above. 

Even when there’s something like a Hawaiian shirt in summer, it’s sandwiched between the familiar jeans, loafers, white tee and army shirt. 

It’s a lot easier to swap in a Buffalo-check overshirt or a camel polo coat when you know what’s going on beneath is consistent and versatile. 

“I never really decide the day before what to wear,” says Alessandro. “Generally when I wake up in the morning, I don’t even look if it’s raining or there’s sun, and I dress according to what at that moment makes me feel better.”



Of course, Alessandro wears other things as well. His feed is full of exceptions. But there is a pretty consistent core, and the point is that core is easy and practical. It’s a nice option for a casual equivalent to the navy blazer, grey trousers and white/blue shirts we’re all familiar with from formal clothing. 

I know one reader who, for his casual clothing, asks his local shop to just give him anything and everything Squarzi wears. I wouldn’t go that far, but I can see why he finds it so appealing. It’s rare for a casual wardrobe to look so good and yet usually so understated. 

Top image and cowboy hat image, courtesy of Edward Green. All other images, from @alessandrosquarzi or @fortela_


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Thanks Simon, I enjoyed this article. Alessandro clearly has great style and makes dressing look fairly effortless. I’ve always found white jeans to be too bold a trouser choice for me personally and am incredibly jealous of how relaxed and at home he looks in a garment that I would struggle to feel comfortable in (as much as I like the look). I suppose I might just be a product of a more conservative British culture although that excuse only carries so far. After all, I am addressing this comment to a chap from London who is known to enjoy white jeans himself.

Thinking through the above then made me reflect on some recent PS articles focussed on women and how they dress. Most seem to have no such issues being expressive, certainly in comparison with men. I appreciate that perhaps sounds like a generalisation but I think it is probably accurate. It highlights an affliction suffered by many of us males.

Anyway, I suppose the above is just an example of how the site can help us all better understand our clothing choices and to occasionally challenge them. It has certainly helped me overcome my avrrsion to loafers previously driven by apprehension that they are not (currently) the stock choice of footwear for most men! Maybe over time I’ll reach the same place with white denim.

All the best and keep up the good work.


Bradley Tompkins

Maybe starting with something like an Ecru would be a way to “ease” into it. But this comes from a white denim enthusiast!


My wife hates the word “ecru” when I mention it in a “raw denim” obsessive context. Might be fun to get a pair indeed. ?


I think you should go for a nice pair of white (or off-white) jeans Scott! Summer is coming and it will just take a couple of short wears – maybe a Sunday afternoon with a relaxt shirt or t-shirt as suggested by Simon or some evenings during a holiday – to get used to the idea and you will never look back. Is my guess on the basis that you really like the look. I find as with most new things (new glasses, new hairdo, new style of jeans or shoes but also things like going to a new gym or sportclub) it boils down to getting used to something for a short while, not just you but also your environment, before settling in. The concept of this looks amazing on others but not on me is often misconceived


Yes, I have a pair of white Levi denim jeans. I wore them all day once and they got a few little spots on them now and look so much better.


I agree, Jan. A couple years ago, I was taking a short vacay at what we refer to as “down, the shore”, a beachfront town for mostly working stiffs like me. I had packed a pair of newish, pristine chinos. I felt a little self-conscious wearing them out to dinner. After a shower, I gave it a moment’s thought, took the chinos off the hanger, and held them by the legs and whacked the H out them a couple times against the open bathroom door. Donned a loose-fitting navy tee, some soft brown loafers, and strutted my stuff down the boardwalk to the restaurant. I smacked the stuffiness out of them. Summer’s here Scott1 Go for it, friend!


A late reply here:
though I like Alessandro’s style a lot, pairing white jeans with a heavy parka clashes too much, mainly in terms of weight and season… and in this case, with red parka, the color clash is too much.
Try white jeans (as he does in photos higher up) with a conservative, light weight, blue sweater or sweatshirt or something light grey. The key with white pants of any sort is to play down their brazenness with safer tones up top… and the old rule of “no white beyond the warm weather” is a good rule to observe even in our unruly times.


One thing you understated in my opinion: Yes, he is an avid dresser mastering simple ingredients but one of his sucessfull codes is combining a huge collection of watches. That stands out.


Very interesting! i have been following Alessandro for many years and i could not put easily in words what attracts me to this casual way of dressing. At the end, it is classic pieces and standard colour combinations..but most importantly the attitute: wear whatever you feel like and enjoy the process. One thing i observed about his loafers (as i see it on Jake from angloitalian): It does not seem that they become obsessive about taking care of shoes (talking about suede). It creates such a charming outfit..which makes me wonder if it’s worth it to come back home everyday, brush the loafers, put tree shoes into them straight away and deal with them as the most valuable possesions.



hi Akis, I agree with your observation on the shoes. Personally, I like shoes that appear to be cared for but not fussed over. That means I use shoe trees in the evening but almost never shine my calf leather or brush my suede shoes. I find the well worn look more elegant and relaxed than shoes than shoes polished to a mirror shine.


Sounds about right, i have to follow this way of treating shoes from now on 🙂 i was always following the guides from C&J how to make the shoes look new. Indeed they look new but i don’t get the satisfaction of a well worn look. Agree on shoe trees though.


Yes, it is indeed something I should do more often but it somehow always gets overtaken by other things to do.

Shifting gears slightly, I had heard of Alessandro Squarzi before but never really paid much attention to how he dresses. What strikes me as unique about how he dresses is that he manages to do in a very authentic way a number of things that other people you see online try to do but less successfully.

For example, there is nothing really novel about the individual elements like wearing silver jewelry, impressive watches, pairing vintage with more tailored elements, no socks with loafers, but he manages to full this together in a way which feels very authentic and not forced.


Hey, Simon! I’ve found that almost exclusively I’m using Neutral polish, so that the leather is allowed to show through, and not the color of the polish. Couple strokes with a soft-bristle brush and a swipe with a rag, and the shoes look well cared for, but not military-shined.


I have never heard of this man, nor of his reputation. And based on the photos in this post, I don’t think he’s a particularly good dresser.

He has a consistent aesthetic and does look very much relaxed, but the proportions of his outfit don’t really flatter him and there’s nothing remarkable about his color, texture, or compositional choices. I guess not many people are wearing two unbuttoned shirts or a henley and neckerchief with a wool vest and camel coat, but that’s probably for the best.


Steve Bannon killed that concept for me

R Abbott

Agree. It’s fair enough to call it a style, insofar as there’s a consistent theme. But it’s not an elegant style. And not just because it’s casual — I’ve seen some people dress very casually while still retaining a certain elegance. It just looks shabby and messy. And when someone with a social media presence posts a bunch of these pictures (obviously for public consumption), it risks looking contrived.


I agree that stacking long untucked layers is the thing that annoys me the most about #menswear enthusiasts that are most into casualwear.
To me it feels like throwing clothes on a mannequin rather than someone actually wearing things.
Besides that, I do find this style a bit boring. I like some of the finishing touches (watches, bright outerwear) but that’s all. And even then never been a fan of multi-patched military style jackets.

Peter Hall

I’ve been a fan of white jeans for many years. It took a while to break the habit of pairing them with navy or appearing too fussy with multiple layers on top.

With this level of casual wear,you can become really creative with belts .


Where does he live and shop? The style is very American (but not Ivy) rather than European. Apart from the footwear, there’s not much information on his preferred brands.


Thanks for a great article, Simon. I admire the simplicity of Alessandro’s style. I also admire the fact that he looks completely at home in what he wears. I couldn’t carry off his style (much as I would like to), but that doesn’t matter, nor does it detract from the lessons that there are for all of us in the way that he dresses building around a core of a few tried and trusted favourites.

Over the years, I have accumulated a wardrobe full of beautiful clothes, but too much of it has only rarely been worn. There are good reasons for this: I changed careers from one where I wore a suit and tie every day to one where the dress code was “comfort before all else”; I moved from London to the country; and most recently I retired. But a lot of it is because, after a lot of trying, and failing, I am closer to knowing what works for me. in recent months I have sold considerably more than I have bought. Finally, this year I have taken a three month trip abroad, further whittling down my core wardrobe. And yet there are still clothes hanging in my wardrobe here which I have yet to wear!
The whole journey (forgive the oun) has been very liberating. Thanks for all your advice and virtual help in getting there.
All the best.

(PS: I am creeping towards trying white jeans; so far, I have got as far as ‘stone’!)


Hi Simon and Adam,
Adam our clothing journey appears very similar and I completely agree with your comments. I too have sold much of my older wardrobe pieces and would like to highlight Marktt, as a great place to sell good quality clothing, who in my experience provide an excellent service.
My takeaway from Alessandro’s style inspiration is the overall approach more than specific looks. Something previously covered on PS.
I personally like many of the looks and the effective layering. In common with Adam’s and other comments, I haven’t quite made it to white jeans (whilst appreciating Simon’s gentle encouragement), but have got as far as natural. Not sure if it’s Britishness, the prevailing weather in England or skin tones.
Alessandro is definitely a great addition to the ‘how to dress like’ collection and for me an inspiration especially to a more mature man.
Btw I really like the zip sweatshirt which is unfortunately out of stock in my size at the moment


I’m a great fan of Marrkt too. What I get from my sales I use to invest in a new piece which fits well with the ‘capsule’ or adds a detail. Scarves in the winter are a favourite.


Throw a couple of sports jackets into the mix and get rid of the patterned vans and this man more or less dresses exactly how I aspire to dress myself. It’s elegant, cool and a bit rakish.


I think one of the key elements of Squarzi’s style is the way his grooming aligns with the clothing and the way he wears it. His longer, slightly unkempt hair and the stubble/beard give the same relaxed attitude as the faded jeans, untucked chambray shirts, canvas sneakers and bohemian accessories, so it all looks cohesive and (most importantly in my mind) authentic. Some may not like Squarzi’s style, but it’s hard to argue it doesn’t have genuine character.

Simon, have you thought about an article focused on the ways grooming can impact style or the role it plays in the success of a particular look? Cheers!


Good point! The glasses too work well with his style. Perhaps that’s another theme for an article, Simon?


John- that is a great idea. Particularly when dressing with a “vibe” as Squarzi does, grooming in relation to clothing carries weight.

Another aspect, Squarzi looks like he is smiling or just finished smiling in nearly every photo which is also part of this style as opposed to the “staring into the middle distance with a hand in a pocket pulling back a perfectly folded jacket”.

William Kazak

Very interesting discussion about finding clothing that keeps it simple for oneself. His choices are not my choices which is ok for both of us. I have been wearing a RL pair of stone colored painters pants/carpenter jeans. They are a heavy denim, loose fit and are somewhat robust for Midwest USA winters. I see people that I know who wear denim top and bottom. Not my style at all. They look too casual with not much thought to it. Too frumpy. I purchased a white pair of Levi’s 501 that I have yet to wear. Maybe I am waiting for summer to appear or maybe the tighter fit is not really my style. I don’t really know that yet but I do like my linen trousers in the summer. Leather or canvas shoes work well for me. Loafers won’t stay on my feet. I quit wearing them many years ago. I need a shoe that ties tightly with laces.


White/blue jeans with a white T shirt and other various tops. It’s not rocket science and it’s not really a particularly individual or innovative “style”


Regarding brands: we definitely have to mention Alden when we talk about Mr. Squarzi’s shoes. He might wear them almost more than EG. I used to follow his style more some years ago. Lately I saw some of his jeans with an ironed crease, which somehow ruins the rest of the nice look for me. (Normally I am not that narrow minded, but creases on jeans are a red line for me.)

Sadly the so versatile mid blue jeans are hard to get (if not vintage) without looking totally fake. Simon, you probaby remember this because of your nice fullcount dartford model. I hope Rubato or some other trustworthy brand can help there in the near future. Until then I will keep washing my dark indigo ones…


Just ordered some Full Count Dartford last night. Hoping they meet expectation on the fit and fade!


Good luck! The fit is enormous, as you probably know.

Paul Webber

I think context is very important here.

Having lived and worked in and around Milan for many years, I would say that Alessandro’s style, whilst not commonplace, is far from unique. This combination of colours, fabrics and accessories tends to be the starting point for many, and is increasingly popular amongst those who are moving past their 40s in terms of age but who want to stay stylish, and yet don’t want to look as though they are trying to be young.

So it works because it doesn’t shout or stand out. No doubt he feels very comfortable with this, as would the people around him.

Without this context, it would jarr. I suspect wearing it in Burnley or Slough would attract just a little too much attention

Paul Webber

But surely if you tone down a look it stops being reflective of that certain style which drew you to it in the first place?

Blue jeans, chambray shirt and navy outer layer is not really a style in my eye. It’s just everyday items which complement each other, no?


I suspect you’ve never been to Burnley 🙂

90% of these outfits wouldn’t attract any attention whatsoever. Plus, there are plenty of young and not-so-young men in the towns you mentioned wearing the more experimental end of the Stone Island range of jackets. A red coat is hardly going to turn heads.

Paul Webber

Thanks Ray. Was born there and go back regularly to see family actually! But maybe my many years in Italy have blurred my judgement!

Nicolas Strömbäck

Agreed. I think all the How to dress like articles shows the importance of context, which I believe is part of what PS wants to cast a light on. Living in Sweden, if I were to dress similar to Alessandro with all the jewellery I would most certainly stand out. In my opinion it doesnt fit us Northern Europeans as well either. The Italians pull this off with such ease, presumably having lived like this for a long time with the warmer weather and all. In Sweden people mostly dress to fit the colder, harsher weather. It sort of proves this point that Alessandro says he never dresses for the weather but for the mood. That you would not do in Sweden (haha).


Alessandro used to feature in the sartorialist allot back in the day and had quite a different style back then. I remember his style shifting and it being a noticeable contrast. I never felt his current style fully aligned with who I thought he was and I kind of preferred his previous style iterations. It seemed to me his current style cam about in tandem with an increased interest in American vintage and the birth of his brand Fortella. I’ve always found his current way of dressing perhaps a bit ‘trendy’, a bit street wear and maybe more suited to a younger man. I loved Alessandro for the more classic Italian style of the old days (the short haired era) and don’t especially care for the more recent looks.

Matthew V

A very cool guy. Dare I say it, does that Italian innate sense of style, appreciating classic menswear, hi-lo, militaria etc that I have always admired give someone like him the confidence to pull it off?

Matthew V

And I guess while we admire Italian style, a lot of Italian style takes reference / is in admiration of classic English style – Barbours, tweed etc. A mutual appreciation society.

I think when I have been in Italy, I notice the well dressed Italians, especially middle aged men still making an effort, and do wonder if we give up a bit beyond a certain age as a nation, but maybe I am seeking out those well dressed Italians, almost anticipating them and over emphasising, so as you say I am generalising.

What I have noticed in Italy to the places I have had the chance to visit, there still seems to be individual multi brand shops in smaller cities that provide great clothes, something perhaps we have lost (or in some cases never had?) in smaller towns and cities in the UK, with a few exceptions of course.

As said in another comment, Alessandro has moved away from tailoring, but then that perhaps mirrors your (and many other people’s) experience as we enter a more casual, post lockdown world.

Matthew V

I’m sure we will all do our best!

Eric Michel

Nice watch collection… but a white T-shirt on a washed denim will always look much better on James Dean. Personally I stopped after I turned 40, except maybe in Mykonos in August.

Michael Murray

Simon, curious if you’ve ever thought of doing a PS Jean/denim? I can only imagine how popular that would be everyone!

Michael Murray

That makes sense when explained that way. Great perspective on the rationale for the PS creations. Cheers!

Bradley Tompkins

Great piece. I see the key takeaway as the fact that in our ever increasingly casual world, you do not need to 1. succumb to the trend, and 2. you don’t have to fight the trend. Alessandro works with the trend and still maintains the look of effort and style. The devil is in the details…for example, his post from Feb 19th, he is wearing mid-blue denim, white tee, colorful flannel shirt, suede tassel loafers, and bright-ish yellow socks. The detail is that the yellow in the socks ties in a minor color from the flannel…..just enough to show the effort, and subconsciously someone seeing him would comprehend his style.


He always looks great, and he also seems like a guy who really enjoys life.
I’ve definitely taken some cues from him over the years, particularly the white jeans and trying out suede tassel loafers with denim.


I would enjoy life too if I shopped for a living!


Hi Simon,

I’m curious how Alessandro (or your own interpretation of his style) would adjust for cooler climates where footwear and outerwear would need to withstand the elements of autumn, winter, and early spring. A t-shirt seems to be a bit odd, even if layered, in colder weather, but perhaps that’s what’s intended no matter the elements (as Alessandro suggested near the end of the article). Cheers.


The “worth a decent flat” watch collection doesn’t hurt either…


99% of people I see with expensive watches have 0 style, so I would argue this is a very minor detail. His style would not change for me if he would be wearing cheaper watches with a similar style.


An interesting post as always. I’ve seen Alessandro on various menswear blogs and he has quite a following. To my eye, though, he’s certainly stylish but not well-dressed. If I had seen the picture of him in jeans, Hawaiian shirt and US Army jacket without context I would have thought this is a man who cares nothing about clothing and he’s ready for yard work. And yet, the whole look is intentional and curated. It seems to me Alessandro, Ethan Newton and a few others, with their eclectic assemblies and extensive tattoos, are pushing the outer limits of costume rather than offering a vision of creative permanent style.


So, after all the hoohah, we back to t-shirt and jeans. We are all victims of it all, maybe if you think about it, there is a reason why so many men are wearing t-shirt and jeans after years of suits.

I probably have more clothes than most, so I am a victim too, but at the end, wear what pleases you, wear what makes you comfortable for your personality to shine.

JJ Katz

Interesting article, as always. It might be heretical to say so, but aside from being handsome and arguably charismatic, I’m not really sure that Mr Squarzi dresses all that well. My standard of dressing well is if a more “dad bod”, maybe bald, middle-aged guy changes into clothes X (and is comfortable in them, of course), does he look clearly better than in average Y set of clothes? I don’t think these really meet that standard.

JJ Katz

Personally, I find the “looseness” perfectly OK. It looks and probably is comfortable, easy. What I find less appealing (again, translating it perhaps to a more generic physical specimen) is jeans and white-T. I think it’s difficult to really add a lot of value with that compared to, say, a nice suit, shirt, tie, etc.

Peter Hall

Well worn denim should match every wrinkle of the owners face.

There is definitely beauty in worn denim.


The article is interesting, especially for those that want to find inspiration to spice up the most casual side of their wardrobe. That said, I personally find Squarzi a bit overrated. He surely exudes personality and kudos to him for having built his own personal brand, but I find several of his style choices rarely flattering. He reminds me a bit of a grown man that tries hard to look young and cool. Nothing wrong with that – and surely that style resonates with his audience, but it just does vibe with me. Thanks for posting though.


I’m glad you did this profile. I’ve been following Allesandro on Instagram for a while. I’m a decade younger but am going gray and don’t have much use for tailoring day-to-day. Even though my style is a little more muted than his (and I don’t have any tats …), Allesandro has given me a lot of inspiration. The appeal for me is that he manages to make casual dressing as an older guy look fun. He harks back to relaxed, classic, youthful styles, elevates them with high-end pieces, and manages to rein it in just enough that he doesn’t look like he’s trying to dress younger than his age. That is no small feat. I think a lot of it comes down to smart deployment of high-end loafers and canvas slip-ons.

The Shopkeeper

Alessandro Squarzi’s reputation as an honest, genuine presence in the industry is well-respected. His signature style has been more than influential in the menswear world over the last 5 years, or so. 

He clearly has a passion for clothing & craft, and it’s refreshing to see this level of authenticity.

Good topic Simon – Great article!

R Abbott

Can’t say that I’m particularly impressed by anything I see here or any reason why I would want to dress like Alessandro. Some of the pictures are just unflattering. For instance, the second picture from the top showing Alessandro sitting on top of the stairs wearing jeans, a grey sweatshirt, and his legs splayed apart. Don’t see anything remotely elegant here. Or the various pictures of him wearing jeans and a white T-shirt (sometimes barefoot, sometimes not). Not sure what this is supposed to show; don’t see anything novel here. I don’t have anything wrong with tattoos and they can be an interesting form of personal expression, but aesthetically speaking, the picture of him wearing the olive trousers, the short sleeved denim shirt, and showing the palm tree tattoos that go from elbow to hand strike me as “beach bum dressing up for the day.” And the picture of him smoking, wearing paint-spattered jeans, with an olive jacket half on half off neither elegant nor attractive. 

There are a few nice pictures here. I like the picture of him sitting on the desk (medium wash jeans, navy sweater, shoes). I also like the color combinations in the picture with the off white trousers and cream-colored sweater. But don’t see anything I haven’t seen before. 

Massimo Pasinato

Hi Simon it is always nice and interesting to read your articles.
I decided to write to you because I have known Alessandro Squarzi for only a few years, but we immediately hit it off. I with my more classic and conservative taste, he with his more ‘comfortable’ one. I started making him some bespoke suits with very refined vintage fabrics, until I came to create exclusive jackets designed by him for his brand. Just the other day I did a trunk show at his Fortela shop in Milan, precisely to combine our 2 styles, creating a right mix that people really like. 
see you soon, ciao Massimo

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That Alex

Yo Simon,

Cool piece. I think the bloke looks really good an’ all dat, but it set me thinking. Is it possible to look this relaxed and sexy without conforming to the accepted menswear language? That’s not a criticism of his clobber, by the way, more of a philosophical musing.

I’ve seen geezers who I think manage both but I got weird taste. I suspect, for most people relaxed and sexy is the polar opposite of unconventional or non-conformist.

Love your work. Much kisses.



Thats to me the most interesting article of the year since to my surprise i didnt know allessandro but my style has many similarities to him with main differences that i use more black instead of blue and i hate army stuff. Have you ever thought how many clothes are considered a capsule ?


It’s interesting that some people consider this guy well dressed. He made his name through The Sartorialist with tailoring and people fetishize an old Italian with tattoos and vague sense of edge. But all of these outfits are cringeworthy and look awful on him. He does NOT pull off the Americana look and seems like the clothes are wearing him. It’s cool that he dresses the way he likes, but no reason to celebrate his style at this point. It’s not easy to step outside one’s lane.

Zak Wagner

Alessandro is a hero for those of us living in a world where more formal clothing doesn’t work. I love traditional menswear, suits, sport coats, tweeds etc. But living in Colorado, there is almost no need for these pieces. When I wear proper shoes to the office I get comments on my “fancy” shoes. If I wore a blazer, I’d stand out more than I’d want to. Alessandro has shown ways to dress smarter in a casual way and show a lot of personality. I’m the same size as my father and grandfather, and because of that, I have some great vintage western and Woolrich pieces. I wear that, with my heirloom turquoise and some loafers and I feel like a million bucks!

A dude

For guys who require zero formal cloth and love military stuff they end up looking like him I think. I am one of them but trying to go for more clean look. I still check his posts because something he is doing is interesting.
I think that most of men cloth are normal and not that interesting by itself. It gets interesting by adding accesories like hats and glasses and shoes, and etc. and tweaking how you wear it. What do you guys think?


Great read and profile. Alessandro’s styles, fits, penchant for military jackets is an aesthetic that looks good on him and one that he is clearly comfortable in and enjoys wearing. Also, some nice ways, which you’ve also talked about in other articles, on dressing more causal looks up with certain shoes or layers to elevate an outfit to less casual. “Authentic” comes up a lot in the comments and I think the profile highlights an importance of finding what stylistically resonates with you and that you enjoy, like it clearly does from Alessandro’s pictures. It may not work for everyone but does for him.

Alec D

Simon, any sense of where Mr Squarzi gets his jeans from?

Alessandro M

Hey Simon,
Thank you for doing a profile on Squarzi. As always, you are very generous.

I have to say, it seems like some other commenters haven’t quite picked up on a couple of great observations you make throughout the article. His accessories, watches, loafers, and even his tattoos either elevate his outfits or keep them casual but make them more interesting. It must also be considered that to a trained eye most of his plainer clothing is actually quite remarkable, either because it’s some rare vintage piece or because it’s a Fortela piece based on said vintage.

Remove the accessories, the loafers, and swap the sweatshirts, jeans, and t-shirts to more generic versions and, yes, the outfit is often too plain or casual… but that’s a different outfit!

That said, not everyone can wear that stuff like he does. You can feel he’s not trying hard and, on the contrary, he’s always in his element. Having heard Alessandro speak on a couple of podcasts (in Italian only, sorry!) I came to understand how truly uncompromising and unapologetically himself he is. He literally wears his heart on his sleeve, and it shows.


Love this piece and the inspiration it gives. Less certainly is more. I would love any tips on where to get a decent M65. Everyone I find is either poorly made, too short or poly cotton. Any advice would be gratefully received.


I’ll immediately confess to being utterly bored by blue jeans – there is nothing more to say about them IMO. Meaning that they are so ubiquitous and visible literally every day, and in almost every presentation you can dream up, that drawing attention to the way one person wears them or praising how they fade/crease to become your own really says nothing original at all. It’s quite telling, again to my eyes, how almost all the outfits he wears which include white jeans say something. In contrast with those featuring blue jeans.
I used to travel to Milan regularly and in my own experience I would say that a person who looks like this looks derivative. The look conveys Italian inflection, but it’s mostly a non-original Shoreditch/Brooklyn/[name your trendy place] look.
Sorry, but not much interesting here for me.
Yet….great work Simon, it’d be weird if everything was a hit 😉


If I may: not all blue jeans are the same. Yes, jeans are ubiquitous, but 99% is cheap cotton/elastane which doesn’t really count as denim. Where I live quality (f.e. Japanese) denim, which ages totally different from the cheap stuff, is not ubiquitous at all, but a very rare thing. Maybe a standard in the menswear bubble, quality denim in a classic cut is still a statement in the real world.

Ned Brown

Loved this. Got me inspired to try harder, especially at my advanced age of 71. I’ve got so many clothes, tons casual, in plastic bins. Living in Charleston South Carolina, I put on shorts and an Oxford shirt nearly everyday; it’s about as exciting as flossing my teeth. Thank you. The dude has great style and comfort- absolutely buries the LA and Hamptons set. Cheers,


Love your style, cool


First off, I agree with others that the vaguely defecatory sitting position repeated in many of the photos isn’t doing Alessandro any favors, but I’ve revisited this page several times now mostly to absorb the free lesson about footwear. I think Alessandro’s collection of loafers and the way he deploys them with various trouser-and-sock/no-sock combos is an unmistakable mark that his approach to dressing is much more sophisticated than his mostly artless, ultra-casual outfits might suggest at first glance. Previously, I never would have thought I needed tassel loafers in a dozen shades of brown suede, but Alessandro makes it look like an essential part of any wardrobe. Also: the generous size and graphic black frames of his glasses look great on his expressive face — many people might look cartoonish in spectacles so bold, but they suit him perfectly.

J Crewless

I like his style. Unsure how to describe my appreciation for it. It seems sincere. That may be the best way to describe it.


Alessandro has a great, effortless style indeed. But he also has a smile on his face which makes him look even better!