There was a time, not so very long ago, when street style wasn’t totally concocted for the cameras. Even at Fashion Week. Yes, really.
If you’re reading this and you’re a Gen Z’er —unlikely, I realise, but welcome— you may not be able to imagine such a wholesome époque.
But truly, ‘street style’ became the thing it is today because it was originally rooted in spontaneity. That, plus it provided the kind of addictive voyeurism we now take for granted with socials.
Now, gather round and listen to Granny. You see, there was this lovely, legendary guy in the 90s called Bill Cunningham who rode his bike around the streets of New York photographing whoever just happened to have left their house looking extra-interesting that day. (Ok, I was still a child in the 90s but I’m old enough to have internalised this fashion lore.)
Next, starting in the mid-noughts, came Scott Schuman. Aka: The Sartorialist.
Fast-forward another couple years to when I began being so lucky as to attend fashion shows. Trailing behind my elegant overlords (bosses) making sure they were sufficiently caffeinated and coordinating with their drivers (gotta start somewhere), then peering at what I could see of the runway from the ‘Standing’ section (you basically queue outside until all the important seated guests have gone in, then they hoard you over to the nosebleeds if there’s still time/room. If you, like me, are 23, man are you happy to be there.) Well, back then, being photographed by Scott after a show was the ultimate seal of style-approval.

If The Sartorialist discreetly snapped your photo in a crowd pouring out of a show, you would of course pretend not to notice. Never look at the camera and smile goofily, no matter how Canadian you are deep down, damn it!! Naturally one was chuffed to bits though. This meant you were *officially* stylish enough to be on The Sartorialist.com, an honour in its own league, circa. 2013. (Tommy Ton, Sandra Semburg and Phil Oh burst onto the scene soon after, but they deserve their own FPQs on a different day.)
Back then, it just wasn’t all about Instagram. Or it was just starting to be. We were still in first-generation fashion blog era. Scott never wrote your name on his website. Maybe your first name, if he knew it, but he wasn’t like, tagging your Instagram handle in hopes of reshares or whatever. He’d just note the street he’d seen you on or the show you’d maybe been attending, or the time of day. You knew it was you and that was enough. Sometimes he shot people in the streets of New York or Paris who weren’t even attending shows. Imagine. Just people who happened to have great personal style, standing waiting for the light to change and minding their own business.
Today, The Sartorialist.com exists as more of an archive space, as Scott has (rightly!) migrated to Substack for a longer-form take on fashion. His newsletter is a joint effort with his girlfriend and creative partner Anastasia, who brings wonderful personal style and perspective to their newly-launched newsletter TheSartoriaLIST. (Let’s be honest, they had me at the pun.)
It’s a unique, dynamic-duo, phtographer-muse take on the fashion newsletter that is both personal and collaborative. Scott is also unique in that, as he (also rightly) points out, he has consistently celebrated other people’s style over his own. A commendable commitment in the days of brand partnerships. He’s also honest. I recommend reading how he “went from stay-at-home Dad to Fashion’s Front Row in Ten Months”, for example. Meanwhile, Anastasia, with her years of merchandising experience, shrewd consultant’s eye, and knack for effortlessly mixing brands, adds a discerning female point of view and some excellent wardrobe suggestions. Plus she loved Louise Trotter’s Carven Sesame Street skirt as much as I did, so I know we should be friends.
Here are Scott and Anastasia’s Fashion Proust Questionnaires.
SCOTT SCHUMAN:
What is your idea of a perfect outfit?
Navy crewneck over a blue, striped shirt with navy single pleated pants and white Adidas Stan Smith or vintage Prada shoes
What is your greatest fashion fear?
Cowboy boots, fringe, western shirts, cowboy hats, bolo ties, boot-cut jeans wait, I think I’m seeing a pattern here!
What, in hindsight, is the worst outfit you’ve ever worn?
I’ve always been happy with what I’ve bought but because I love fashion I’ve often bought pieces that are “important” for the season but didnt necessarily look good on me. Once I narrowed my wardrobe to a few colors and focused on fit I’ve been much happier.
What is the worst outfit you’ve ever seen on someone else?
I only notice what I love and never judge or really even notice the things that I don’t , I find its a much happier way to look at the world.
Which living person’s style do you most admire?
The personal style of Giorgio Armani and George Cortina is a close second.

What is your greatest extravagance?
I’ve been very lucky to have friends that are tailors and will gift me a bespoke suit. The difficulty is staying the size of the suit over a certain number of years. However, I should admit I can still wear clothes I wore in high school, if I ever wanted to wear parachute pants again.
What is your current state of mind with regards to the fashion industry?
It’s become super segmented like music or movies with no clear leaders that create an overall direction for fashion. Fashion magazines have also really let us down by pandering for the most clicks instead of offering a expert eye and opinion.
What do you consider the most overrated style virtue?
Being skinny
On what occasion do you lie about someone’s outfit?
I don’t, I just focus on what I like, however if I make a photo that is from the knees up then its probably bc the shoes weren’t great.
What is the quality you like most in a man’s outfit?
Good fit is the single most important element of a mans wardrobe.
What is the quality you like most in a woman’s outfit?
Fit is also important for women but there is more room for irony in how they dress.
Which fashion trend do you most despise?
OVERSIZED! Oversized should mean a silhouette that is a little bigger or a little more exaggerated than normal not just giant sloppy mess that has no sense of the body underneath. It’s lazy unskilled designed (Balenciaga ) but also lazy shoppers.
Which words or phrases do you most overuse when describing fashion?
Chic!
Which runway collection in history was your greatest love?
Prada mens and womens collections from like 2011 to 2017 were all really great! Marc Jacobs had some great New York shows and of course Dries van Noten shows were always great.
When were you happiest with your own look?
Summer of 2022 when I started dressing more simply and was in great shape!
Which designer’s talent would you most like to have?
Giorgio Armani from 1985 to 1990, Romeo Gigli from 1988 to 1992, Dries van Noten from 20005 to 2016.
If you could change one thing about your wardrobe, what would it be?
I’m pretty happy with it now. I feel chic but it also allows me to do my job without worrying about how my clothes will hold up.
What do you consider your greatest achievement, career-wise (so far!)
Creating The Sartorialist which remains one of the only fashion social media accountants that is about celebrating the style of others not just myself.
If you were to die and come back as a fashion item, what would it be?
Maybe a great pair of shoes !
Where on earth do you get the most style inspiration?
I moved to Milan because it is simply the most stylish city in the world! Of course Paris, New York and London are also very chic but Milan is a quarter of their size so the density of style here is so much more evident.
What is your most treasured possession?
I still have some old Giorgio Armani shirts from 1986 that I begged my parents to buy for me as a Christmas present! I loved them so much I didnt unfold them from the packaging for a month or two! It took me forever to have the nerve to wear such precious items on my own body ! And I can still wear those shirts to this day.
What do you consider the lowest depth of fashion rock-bottom (ie. Karl’s sweatpants)
Dirty clothes or clothes that are made to look dirty on purpose.
What is your favourite fashion-related occupation?
Photography or a fashion historian.
What is your most marked style characteristic?
Cuiosity is an underrated character trait of really stylish people.
Who are your favourite fashion writers?
Im a visual person so photographers like Bruce Weber or Paolo Roversi or Aldo Fallai made a big impression on me.
Who is your style hero in fiction?
Dickie Greenleaf of Talent Mr. Ripley or C.K. Dexter Haven (Cary Grant) in Philadelphia Story.

Which individual that you know (or have known) personally most influenced your style?
Giorgio Armani from 1985 to 1990 for his personal style and design style
What is your style motto?
Form follows function is a failed experiment.
ANASTASIA NOVAIA:
What is your idea of a perfect outfit? Something that I imagine as the most empowering for me.
Old Prada FW2007 blazer, Levi’s vintage 501 jeans, Terry toweling sweatshirt, classic loafers, Chimi sunglasses + something sparking (earrings, necklace, bracelet or all together).
What is your greatest fashion fear?
After so many relocations, my greatest fear is accumulating too much stuff. Every season, I make it a point to declutter and resell.
What, in hindsight, is the worst outfit you’ve ever worn?
I was pretty bad with teenage rapper style experiments. Such a blessing there are almost no photos from those times.
What is the worst outfit you’ve ever seen on someone else?
Can’t say one, but I’ve been to Pitti Uomo several times, so if you know you know :))
Which living person’s style do you most admire?
Jenna Lyons always remains my crush.

What is your greatest extravagance?
Everything feathered!
What is your current state of mind with regards to the fashion industry?
Endless hope. And I’m always happy when Miuccia Prada reinterprets her archives.
What do you consider the most overrated style virtue?
Good taste and polished looks.
On what occasion do you lie about someone’s outfit?
When my 10 year-old daughter asks me about her fashion designs. I always love them ;)
What is the quality you like most in a man’s outfit?
Length of the sleeves and pants :)) I’m 174 cm height and have pretty long arms and legs, so usually I buy a lot from men’s department.

What is the quality you like most in a woman’s outfit?
Color combinations and textures. These are the first things that attract me.
Which fashion trend do you most despise?
Quiet luxury for a cost of one dinner.
Which words or phrases do you most overuse when describing fashion?
Too commercialized.
Which runway collection in history was your greatest love?
Prada FW2007 without doubts.
When were you happiest with your own look?
Since after COVID, very often actually, I then realized that I have treasure cave wardrobe and started to really wear it instead of just collecting. Cause if not right now when?
Which designer’s talent would you most like to have?
I’d like to have more of Katie Grand’s styling talent!
If you could change one thing about your wardrobe, what would it be?
Wear more crazy heels, but I’m pretty lazy and busy mom now.
What do you consider your greatest achievement, career-wise (so far!)
That I worked in the best companies, creating and inspiring best teams, and that I still really love what I’m doing even after 17 years in this business!
If you were to die and come back as a fashion item, what would it be?
Let it be Dries sparkling necklace that I just received as a New Year’s gift. It’s so so beautiful, but also complicated, spiky and hard to handle.
Where on earth do you get the most style inspiration?
When I’m walking alone across quit streets of Milano.
What is your most treasured possession?
My daughter’s early childhood photos.
What do you consider the lowest depth of fashion rock-bottom (ie. Karl’s sweatpants).
Looow-rise jeans that expose underwear, whether on men or women
What is your favourite fashion-related occupation?
Besides my own work as a creative merchandiser and buyer I’d say Visual merchandiser. I like the idea of creating worlds based on numbers.
What is your most marked style characteristic?
A mix of masculine basics and feminine statement pieces with a bit of sparkles.
Who are your favourite fashion writers?
Alexander Fury, Colin McDowell and Charlie Porter.
Who is your style hero in fiction?
Pippy Longstocking.

Which historical figure’s style do you most identify with?
Manuela Pavesi, if she’d styled old J.Crew catalogues.
Which individual that you know (or have known) personally most influenced your style?
Scott Schuman when he first took a picture of me 15 years ago. And now of course :))
What would you like to wear to your own funeral?
I’d like to wear the outfit I described in the first question. It perfectly captures how I’d want to be remembered — classy, a bit eclectic and undeniably me.
What is your style motto?
‘If not right now when?’ indeed ;)
With thanks to Ellen Brecken Mihalovich for all of the artwork in this week’s newsletter.
He understands my SOUL. Please let us be rid of oversize!
gen z big fan over here! :)