By Nick Catoggio
Wednesday, March 11, 2026
You can tell a lot about a man from his shoes.
Women in particular seem to think so, as dating advice
for men that comes from the opposite sex reliably includes exhortations to make
sure your footwear game is on point. When I asked one of my editors this
morning whether she pays attention to a man’s shoes on a date, she said
no—unless he’s wearing sneakers, which is a red flag. Or conspicuously nice
shoes, which is a green flag.
So, yes.
I’m invested in the idea because I’ve become a shoe guy
in middle age, probably for the same reason that I’ve become a watch guy. As
one’s looks decline, the urge to compensate by decorating oneself with shiny
nonsense increases. Wear nice shoes and a nice timepiece, and others are less
likely to notice the glare reflecting off your scalp or the fact that your
facial skin is starting to slide downward like that of a Nazi who just
opened the Ark of the Covenant.
Shoes are also a respite from the political muck I’m
forced to wade through every day to find material for this newsletter. We all
need pleasant diversions from the end of the American experiment; mine is
playing with the customization tool on Carmina’s website.
Imagine my delight, then, as I conducted the daily
muck-wade through political news earlier this week and stumbled across a story
about the president’s interest in footwear.
Donald Trump is also a shoe guy, it turns out. (Sort of.
More on that in a moment.) He’s so much of a shoe guy, per the Wall Street Journal, that he’s begun gifting
footwear to everyone from Cabinet members to distinguished White House guests
like Jew-baiting demagogue Tucker Carlson. “Marco, J.D., you guys have sh—y
shoes,” Trump reportedly told his secretary of state and vice president during
a meeting in December before asking them for their sizes.
Soon enough, each man was decked out in a new pair from
Florsheim, the boss’s brand of choice. They’re not alone. “One Cabinet
secretary has grumbled that he had to shelve his Louis Vuittons, according to
people who heard the complaint,” the Journal reported.
Louis Vuittons cost north of $1,000. The Florsheims the
president is foisting on his cronies typically run $145. And in multiple cases,
it appears, the sizing is off to a comic degree: Recent photos of Marco
Rubio and Transportation Secretary Sean
Duffy speak for themselves.
You can tell a lot about a man from his shoes. What can
we tell about these men from theirs?
Trump doesn’t know as much as he thinks he does.
I’ll say this for the president: He’s enough of a shoe
guy to have avoided truly egregious crimes against good taste here. (For once!)
His team is wearing oxfords, the appropriate choice to
accompany a suit and tie. He steered clear of hideous Frankenshoes,
which pair a dress-shoe upper with a chunky rubber sneaker sole for comfort.
And he didn’t get suckered by steeply priced but poorly made fashion-house
footwear that commands an exorbitant premium based on brand name alone.
If you’re going to skimp on quality, you should save a
buck in doing so. That’s what he did by opting for Florsheim.
Being gifted shoes by the most powerful man in the world
and opening the box to discover Florsheims is like being gifted a watch,
expecting it to be a Rolex, and finding a Daniel Wellington instead.
It makes sense that Trump would be attached to the brand,
though. He’s a
creature of nostalgia, and back in the day Florsheim was a pillar of
quality American shoemaking. When my mother took me shopping for shoes as a
kid, she looked for Florsheims. When adult men of that era went looking for
something beautiful, stylish, and buy-it-for-life durable, they landed on
Florsheim Imperials in shell cordovan. Those shoes were so well made that you
can find them today on eBay, decades old yet often looking brand new, still
worth hundreds of dollars second-hand.
Like America itself, the Florsheim of 2026 is not the
Florsheim of Donald Trump’s, or my, youth.
Most production moved overseas years ago to Cambodia,
China, India, Mexico, and the Dominican Republic, per the company’s Canadian
website, making its wares an odd choice for a protectionist “America First”
White House. (Icing on the cake: Florsheim’s parent company is apparently suing the administration over tariffs.) A quick search of
its current catalog reveals nothing available in shell cordovan. The price tag
alone should have clued Trump into the fact that Florsheim ain’t what it used
to be: There’s no such thing as high-quality American-made footwear priced at
less than $150, and any real shoe guy would know that.
“Maybe he knows and he’s just cheap,” you say. Maybe—but,
given that he’s squeezed $1.4 billion and counting out of his courtiers since
returning to office, I’m inclined to believe he’d be willing to pony up a
little more than $145 for decent shoes. My guess is that he simply doesn’t know
better. He thinks Florsheim is still the Florsheim of 1975 (when $145 was
top-dollar for a solid pair of kicks) and that he’s doing his deputies a favor
by making them swap out their Louis Vuittons for this husk of a brand.
That’s him all over. He thinks he knows things and
then ends up looking ridiculous when his assumptions meet reality. He thought
a decapitation strike on Iran’s leadership would cause the regime to cave in or
quickly sue for peace. Wrong. He seems to have thought Gen. Dan Caine’s pre-war
warnings about America burning through its air-defense munitions could safely be
ignored, trusting that the world’s greatest military would find some easy way
to counter the asymmetric threat from Iranian drones. Wrong. He obviously thought that the Strait of Hormuz would
remain open once U.S. and Israeli jets were poised to punish Iran from the sky
if regime goons dared to close it. Oh so wrong.
Now he has J.D. Vance and Marco Rubio wearing shoes that
cost less than some Nikes because he thought their previous pairs—which in all
probability were better than Florsheims—were comparatively “s—y.” Wrong.
The Trump Cabinet doesn’t have its act together.
When I asked my editor why she notices nice shoes on a
man, she compared it to him wearing a clean, unwrinkled shirt. It’s not the
shoes per se that make an impression, it’s what they say about his basic
competence and whether he’s worth investing in.
Is he clean? Well-groomed? Capable of putting together an
outfit? Is he willing to make an effort to present himself well and possessed
of the discernment needed to succeed at the task? Showing up to a date in a
T-shirt and Vans signals low energy, poor taste, or both. Showing up in a crisp OCBD and pair of Alden 975s in Color 8 suggests a man who has his act
together. (Emphasis on “suggests.” I own both and rarely have my act together.)
The fact that Trump and his Cabinet can’t dial in on
something as simple as shoe-sizing doesn’t scream, “We have our act together.”
Sizing shoes is trickier than it sounds, in fairness,
especially in an age when most purchases are made online with best guesses
about fit instead of in store after measurements. Even if you aim for reliable
sizing by doing most of your buying from the same brand, it’s easy to end up
confounded by the variety of “lasts” (i.e,. foot shapes) manufacturers use for
their models. Scroll through Carmina’s
menu of lasts and see how confident you are that you’d nail a fit on the
first try, bearing in mind that rolling the dice on an order there will easily
run you $500 or more.
It’s easy to miss the mark on sizing. But, being a
sentient adult, I’ve never missed so badly that I ended up looking like a
6-year-old wearing my dad’s shoes, which is how Rubio
and Duffy look in their footwear.
I don’t think stupidity is to blame for that, though. I
suspect it’s something worse.
It’s not that Rubio and Duffy don’t know their shoe size.
Nor is it that Trump’s gophers are incapable of placing orders in the correct
size at Florsheim, a task that a reasonably intelligent chimp could be taught
to carry out. My guess is that, whenever the president asks his toadies what
size they wear, they deliberately inflate the number to impress him with
how big their feet supposedly are.
No joke: According to the Journal, at the same
December meeting at which Trump asked Vance and Rubio about their shoes, he
reportedly observed, “You know you can tell a lot about a man by his shoe
size.” In an administration of postliberal cretins consumed with “strength” and
machismo, what more humiliating admission could there be than telling the boss
you’re not well-endowed?
Below the ankle, I mean.
Thus it was that Rubio, a man who stands 5-foot-9 or 5-10
and whom the president once famously derided as “Little Marco,” reportedly told
Trump he takes a size 11.5 shoe. And for some reason, instead of quietly
swapping out the gifted pair for an appropriately sized replacement from
Florsheim, the secretary of state evidently feels obliged to walk around in
them. (Is he afraid the president will make him take them off to check the
size?) If I were Volodymyr Zelensky looking to buy some goodwill from the White
House on the cheap, I’d airlift a set of tongue pads and orthotics to the State
Department immediately.
Cabinet members wearing wrong-sized shoes on purpose is
what happens in an outfit that doesn’t have its act together. Already so far in
the war, which is less than two weeks old, the administration has been
surprised by Israel’s choice of targets, by the sudden spike in oil prices last Sunday night, by Iran’s
decision to attack its oil-producing Arab neighbors, and of course by
the closure of the Strait of Hormuz. Yesterday Sen. Chris Murphy emerged from a
classified briefing claiming that the
White House had no plan to reopen the strait, one of the most
foreseeable and economically ruinous consequences of the conflict.
That smells like Democratic hyperbole—until you read the
reporting today about how grim America’s tactical options have become. One
source told Reuters that the U.S. might need to take control of Iran’s
coast somehow before oil tankers can safely resume transit, as there are too
many ships bottled up and too few U.S. vessels available for military escorts
through the strait to solve the problem. Even if escorts were feasible, The Economist notes, they’d be fabulously expensive
and would proceed too slowly to avert a major oil supply shock.
Oh, and if a tanker is attacked and its cargo spills out
into the Strait, that alone could impede commercial traffic for months.
When you’re stalled in a gas line this summer, wondering
how you ended up there, think of Marco Rubio parading around in his dad-sized
shoes at the president’s behest.
Trump’s Cabinet is too cowardly to resist his
stupidest ideas.
Still, if we’re searching for a grand lesson from l’affaire
Florsheim about how this administration operates, there’s an obvious one
I’ve overlooked.
It may be that the president’s deputies understand that
Florsheims are trash, that he’s foolish to gift them something as
size-sensitive as shoes, and that they look like dopes all wearing the same
model of ill-fitting footwear. The problem isn’t that they don’t have their act
together. The problem is that they’re part of an authoritarian cult of
personality and that such things are governed by very particular rules.
Never be the first
to stop clapping for the leader; never tell him his idea to wing it in a
war that could wreck the global economy is stupid; and never tell him “no
thanks” when he hands you a pair of shoes. Rubio et al. aren’t wearing their
Florsheims because they lack taste or because they enjoy the feel of sliding
around on a midsole that’s two sizes too big. They’re wearing them because
they’re cowardly suck-ups who are afraid to tell their boss no.
“It’s hysterical because everybody’s afraid not to wear
them,” one White House official candidly told the Journal of Cabinet
members’ habit of donning their shoes around Trump. Everything is a loyalty
test in this third-world political culture, apparel very much included. From
the famous MAGA cap to Republicans’ blue-suit-red-tie solidarity attire outside one of Trump’s
courthouse appearances to the ear bandages at the 2024 Republican convention to the
Florsheim mafia in the West Wing, the president has always cultivated visual
displays of devotion to accompany the rhetorical slobbering.
Not all examples of his Cabinet feeling obliged to egg on
his dumbest impulses are as trivial as bad shoes, though, needless to say.
“Inside the administration, some officials are growing pessimistic about the
lack of a clear strategy to finish the war,” the New York Times reported on Tuesday. “But they have
been careful not to express that directly to the president, who has repeatedly
declared that the military operation is a complete success.” Those two
sentences could be airdropped verbatim into any news report about the Kremlin
officials’ attitude toward Vladimir Putin with respect to Ukraine.
Cowardice explains why we might soon be paying $12 a
gallon for gas and why the most powerful people on Earth are wearing
footwear that even casual sartorial hobbyists wouldn’t be caught dead in. And
so it’s pointless for anyone to offer the president and his team
recommendations on how to improve their shoe game, which is about blind
obedience far more than it is about shoes.
Although, because I know a little something about the
subject, I feel obliged to try.
Do better.
There are a few obvious alternatives to Florsheim for
those who want something made in the USA. and don’t want to wear crap.
One is Alden, widely regarded as the last great American
shoemaker and a favorite of Twitter’s Menswear Guy. I
own eight pairs, five in shell cordovan and one in “rare” Ravello shell that
isn’t part of the company’s regular catalog. Aldens would cost Trump anywhere
from $700 to $1,000 per pair, and he might have to wait a while for his order,
as production is frequently backlogged, especially for handsewn models. But I
suppose he could call up the factory and threaten to tariff them if they don’t
expedite his purchase.
And before you say “he can’t tariff an American company,”
let me remind you it’s his belief that he
can tariff any ol’ thing he wants.
The problem with Alden (besides the price) is that it’s a
standard of Ivy League style and this administration despises the Ivy League, as Ivy League graduates Donald
Trump and Pete Hegseth frequently remind us. So the president could opt instead
for Wisconsin’s Allen Edmonds, another heritage American brand whose iconic
“Park Avenue” cap-toe oxford would fit right in inside the Oval Office. I have
it in—what else?—shell cordovan and wear it to weddings.
Allen Edmonds is famous for offering shoes in virtually
every size that a human foot can realistically be. If you like seeing Rubio in
kicks that are two sizes too long, imagine the joy of watching him waddle
around in shoes two sizes too wide. “Size 11.5—triple E, sir. I have serious
girth.”
If I wanted to spend Allen Edmonds-level money on a shoe,
though, I’d opt for Grant Stone. They’re known chiefly for boots, of which I
have three pairs (two in cordovan, one in kangaroo), but their loafers are very
popular with shoe guys and they’ve built out a nice catalog of oxfords and
derbies. They’re American-owned and the quality is excellent; the only catch is
that they’re made in—gulp—China.
Then again, that may be where the Florsheims are coming
from.
In that case, if the White House is willing to dispense
with “buy American” altogether, I’ve got the perfect suggestion: Vass.
Vass shoes are comparable in price to Allen Edmonds and
Grant Stone yet are handmade, a preposterously good value that’s made
them famous among shoe nerds. How do they manage it, you ask? Well, they’re
based in comparatively affordable Budapest, Hungary—ground zero of Western
postliberalism thanks to the ur-Trump, Viktor Orbán, who’s fighting for his
political life at the moment. Nothing would be more sartorially appropriate for
the president and his Cabinet as it goes about wrecking the constitutional
order than outfitting everyone in pairs of “Budapesters” from Vass. It would be
like giving all of their feet a fashy haircut.
If our clowns are going to wear shoes, they should at
least be good ones.