You don’t need more clothes. You need better timing.
Let’s get this out of the way: most people shop reactively. They wait for an event, a sale, or worse—a trend. A wedding invite drops in July and they panic-buy a blazer. Winter rolls around and they realize their “good coat” is more theory than practice.
But tailoring isn’t built on impulse. It’s built on rhythm. A cadence that moves with the seasons—not against them. When you start dressing with the seasons in mind, style stops being effortful. It becomes instinctive. You know when the linen jacket should come out of hibernation. When wide-legged cavalry twill trousers feel just right. When a sharply cut flannel suit hits that perfect note between practical and poetic.
Paul Newman and his wife Joanne Woodward, 1967. LIFE
Seasonal wardrobing isn’t about owning more. It’s about owning smarter. Thoughtfully. Intentionally. Like you’re building a mixtape for the year—track by track, mood by mood. As menswear historian G. Bruce Boyer once wrote,“True style isn’t about being noticed, it’s about being remembered. And being appropriate for the moment is the most stylish thing of all.”
Style isn’t static. Neither is the weather.
A well-designed wardrobe moves like a good playlist. Upbeat in spring, mellow in fall, rich and layered in winter. It anticipates shifts—subtle and not so subtle—and it’s built to carry you through those changes with grace.
Ingrid Bergman stands on a street as village women stare at her during filming of the movie “Stromboli” on the Italian island of Stromboli, 1949. LIFE.
You don’t wear a velvet dinner jacket in August. Not because it’s wrong. But because it feels off. Just like you wouldn’t step into crisp tropical wool during a snowstorm. The best-dressed people aren’t trend-chasers—they’re in tune. With time. With light. With weather. With their own calendar. That’s what we mean by rhythm. Not a formula. A feeling. We don’t believe in a closet full of “just in case.” We believe in “just right.”
So you build around those anchor pieces.
A soft-shouldered jacket in silk-linen for July weddings.
High-rise wool gab trousers for cool summer evenings.
A sharply cut flannel suit for the grey stretch between Halloween and New Year’s.
A mohair dinner suit that waits patiently all year, then steals the show in December.
Alec Guinness, 1951. LIFE
These are the garments that know when to show up.
The Italians have it figured out.
If you’ve ever walked through Milan or Florence in late September, you’ll notice something: the locals aren’t just stylish. They’re seasonally stylish. They layer cotton-cashmere cardigans when the mornings get chilly. They shift into brown suede as leaves fall. They know their fabrics, and they dress accordingly. It’s not about rules—it’s about rhythm and respect.
As Italian menswear expert Gianluca Migliarotti (of O’Mast and I Colori di Antonio) put it: “Seasonal style is about culture. About understanding where you are and what the day is asking of you. When you dress with awareness, you show care.” There’s a beauty in that awareness. And that beauty lasts longer than any trend cycle.
Wear the moment. Don’t dress against it.
Seasonal dressing isn't about rules. It’s about awareness. Of fabric weight. Of light. Of what you’re doing and where you’re going. It’s not prescriptive—it’s poetic. You’re not following a dress code. You’re tuning into the season like a good jazz musician, playing along with whatever’s in the air.
Leonard Bernstein conducting a rehearsal of the New York Philharmonic at Carnegie Hall, 1956. LIFE
You wear flannel in November not because someone told you to, but because it feels right. You opt for a corduroy overshirt because it softens the chill of dusk in early October. You throw on a raw silk tie in June because the texture catches the golden hour in a way wool never could.
That’s the elegance we chase at Sartoria Wynona. Not rigid formulas or prescriptive guides—but a state of mind. Your wardrobe shouldn’t fight the season. It should move with it. Like a well-cut jacket in a breeze. Like a sharp trouser draping just-so over a pair of suede loafers on a cobbled street.
It’s not about looking perfect.
It’s about dressing with rhythm.
And rhythm, as any good jazz player will tell you, is everything.
Paul Newman in the Florida Keys with guide Jake Muller (left) and friend Mike Hyman, 1967. LIFE
