Pinstripe Shirt: History, Style & How to Wear It (2026 Guide)

A complete guide to the origin, anatomy, and correct wearing of one of menswear's most enduring garments.

In this guide: the origin of the pinstripe shirt, the moment Alain Delon defined it, the five details that separate a good one from a forgettable one, the five rules for wearing it correctly, and four outfits that never fail.

What is a pinstripe shirt?

A pinstripe shirt is a men's or women's shirt woven with narrow vertical stripes — typically pale blue on a white cotton ground — spaced closely together in a repeated pattern. The stripes are woven into the fabric using coloured warp threads, not printed on top, which is why a proper pinstripe shirt reads soft rather than graphic. The pinstripe shirt originated in early 20th-century English shirtmaking and was refined by Italian tailors in the 1930s into the softer, open-collared version most men wear today.

The garment sits at a specific and useful register in menswear: dressed enough to wear tucked under a jacket, relaxed enough to wear open over swim shorts, and versatile enough to move between the two without effort. It is, in the truest sense, a summer shirt built for a life spent moving between registers.

The origin of the pinstripe shirt: from Jermyn Street to the Mediterranean

The pinstripe shirt began in England, at the intersection of city tailoring and Edwardian formality.

At the turn of the twentieth century, London's Jermyn Street shirtmakers — Turnbull & Asser, Harvie & Hudson, Hilditch & Key — had established the modern pattern for the English dress shirt: fine cotton poplin, a rigid collar, single or double cuffs, and a series of restrained stripe patterns woven in coloured warp threads. The blue-and-white pinstripe was among the earliest and most enduring. It signalled quiet office authority — not flashy enough to draw attention, not plain enough to disappear.

By the 1930s, Italian tailors had taken the pattern and softened everything about it. The heavy poplin became lighter cotton. The rigid collar became the colletto italiano — the Italian collar — a shorter, softer, unlined collar designed to sit close to the throat and hold its shape when worn open. The cuffs became structured but flexible, made to be rolled if the day called for it.

By the 1960s, the Italian version of the pinstripe shirt had become one of the defining garments of European menswear — worn by Marcello Mastroianni in Rome, Gianni Agnelli on his yacht in Portofino, and Jean-Paul Belmondo across the streets of the Côte d'Azur. It was the perfect shirt for a specific kind of life: dressed enough to sit at any table, relaxed enough to end the evening with the top three buttons undone.

The Delon moment: how La Piscine fixed the pinstripe shirt in the modern imagination

In 1969, Jacques Deray released La Piscine, a film starring Alain Delon and Romy Schneider, filmed almost entirely at a villa outside Saint-Tropez.

The plot is almost incidental. Two former lovers, reunited by chance, spend a summer alone by the pool. A friend arrives with his teenage daughter. Tension builds slowly, in the heat, until it doesn't.

But the film's real subject — the reason it is still referenced fifty-seven years later — is the wardrobe. And within that wardrobe, one garment appears more than any other: a pale blue pinstripe shirt with an Italian collar, worn by Delon in nearly every scene that wasn't shot in the water.

He wore it tucked into cream trousers. He wore it open over swim shorts. He wore it with the sleeves rolled and the cuffs left unbuttoned. He wore it with cigarettes, with wine, with silence. He never wore it with a tie.

Fifty-seven years later, the shirt is what people return to. Not the plot, not the ending, not even the beauty of Romy Schneider. The shirt. The exact shirt.

For the full story of Alain Delon and the film, read our companion piece: La Piscine: The Style of a Riviera Summer.

The anatomy of a quality pinstripe shirt: 5 details that matter

What separates a correct pinstripe shirt from a forgettable one comes down to five construction details. Understanding them is the difference between buying once and buying repeatedly.

1. The stripe

The pale blue pinstripe on a white cotton ground is the most enduring and versatile pattern in menswear. Thinner is generally better. A hairline stripe reads soft and modern; a wider stripe reads more formal and office-coded. The Delon shirt uses a fine, evenly spaced pinstripe that reads as almost solid pale blue from a distance and only reveals its structure at close range.

2. The collar

The Italian collar is the defining feature of a Mediterranean pinstripe shirt. It is shorter than an English point collar, unlined, and designed to sit close to the throat and lie flat when the top buttons are undone. Without an Italian collar, a pinstripe shirt loses most of its Mediterranean register and becomes an office shirt worn out of place.

3. The buttons

Mother-of-pearl, always. Plastic buttons betray the whole point of the shirt — they catch light wrong, they wear badly, they signal a corner-cutting the rest of the garment cannot recover from. Real mother-of-pearl has weight, warmth, and a quiet iridescence that softens as the shirt ages.

4. The cuffs

Structured but not stiff. Single-button cuffs are correct for the Italian version — designed to hold their line at the wrist when buttoned, but to roll cleanly to the forearm without bunching when unbuttoned. Double cuffs are wrong for this shirt; they belong to a different tradition, a different tie, a different life.

5. The cut

Slim through the body but not tight. The Italian pinstripe shirt is designed to be worn tucked or untucked, and either mode has to look intentional. A shirt cut too full reads as pyjamas when untucked; a shirt cut too slim strains at the chest when tucked. The Delon fit sits in the middle — slightly slim, slightly shorter at the hem, engineered for both registers.

How to wear a pinstripe shirt: 5 rules from the Italian tradition

The pinstripe shirt is forgiving, but it rewards a few decisions and punishes the others. Five principles drawn from six decades of Italian and French Riviera dressing.

1. Choose the pale blue

White pinstripes on pale blue exist, but the pale-blue-on-white version is the one that carries the tradition. Reserve the reverse for winter, and always with a jacket.

2. Wear it open

The Italian collar was designed for an open throat. Two buttons undone is the minimum for casual settings; three is correct for warm-weather leisure. Never wear this shirt fully buttoned without a tie — the proportions collapse.

3. Commit to the cuffs

The unbuttoned-cuffs-hanging-open look is a mistake that has become common. Roll the cuffs cleanly twice at the forearm, or button them at the wrist. Never leave them dangling.

4. Tuck or untuck, but commit

Tucked into cream trousers or tailored chinos, the shirt reads composed and considered. Left out over linen trousers or shorts, it reads relaxed and Mediterranean. Avoid the half-tuck — it fights the cleanness of the line.

5. Pair it with warm neutrals

Cream, camel, taupe, faded navy, off-white. The pinstripe shirt does its best work against natural tones. Avoid pairing it with black or with heavily patterned bottoms.

Pinstripe shirt outfits: 4 ways to wear it

Four canonical outfits, drawn from the tradition and from the wardrobes of the men who defined it.

Outfit 1 — The Delon (Riviera casual)

Pale blue pinstripe shirt, worn open with three buttons undone and the sleeves rolled to the forearm. Tucked or left out over Anovair's Manhattan Pleated Trousers in cream. Leather loafers, no socks. A pair of dark sunglasses. This is the exact configuration Delon wore in Saint-Tropez in 1969, and it remains the correct answer to a summer afternoon in the Mediterranean.

Outfit 2 — The Agnelli (yacht and coast)

Pinstripe shirt tucked into faded navy chinos or Carol Straight Leg Jeans in indigo. Sleeves rolled twice. A woven belt in tan. Leather driving shoes. Optional: a light knit tied loosely at the shoulders. Gianni Agnelli invented this look on his yacht in Portofino; it has never gone out of style.

Outfit 3 — The office (softly authoritative)

Pinstripe shirt tucked into charcoal or navy wool trousers. Top button undone, sleeves at the wrist. A soft unstructured blazer in navy or beige, worn open. Brown leather derbies. This is the Milanese answer to the American power suit — quieter, softer, more difficult to imitate.

Outfit 4 — The evening (dressed but never formal)

Pinstripe shirt tucked into cream tailored trousers, two buttons undone. A fine-gauge cashmere or wool knit worn over the shoulders. Suede loafers. This is the shirt at the end of the day, at a long dinner, in the register that made it a Mediterranean uniform for six decades.

The Anovair Delon Pinstripe Shirt

Our Delon Pinstripe Shirt is built directly from the specifications of the Italian tradition.

100% cotton, woven with a fine light blue pinstripe on white ground. An Italian collar, unlined, designed to sit close to the throat when open. Structured single-button cuffs. Mother-of-pearl buttons. A slim-but-not-tight cut that reads intentional whether tucked or worn out.

We make it in light blue — the canonical shade — and in a slightly deeper dark blue for those who prefer a touch more contrast. Both are built to become better with wear. Both are cut to the proportions Delon himself wore in 1969. Both will still look correct in the same wardrobe fifteen years from now.

Discover the Delon Pinstripe Shirt →

Frequently asked questions about pinstripe shirts

What is an Italian collar?

An Italian collar is a soft, unlined shirt collar with a single back band, designed to sit close to the neck and hold its shape when worn open. It creates a clean V-shape at the throat and is the most flattering collar for an unbuttoned look. The Italian collar has defined Mediterranean shirting since the 1930s and is the collar of choice for a properly cut pinstripe shirt.

Can you wear a pinstripe shirt without a tie?

Yes, and in the Italian tradition it is the correct way to wear one. Worn without a tie, with the top two or three buttons undone and the sleeves rolled to the forearm, the pinstripe shirt reads as relaxed elegance. Adding a tie shifts the register toward office and formal settings, which is the English tradition rather than the Italian one.

What colour trousers go with a light blue pinstripe shirt?

A light blue pinstripe shirt pairs best with warm neutrals: cream, beige, taupe, soft brown, and off-white. Linen trousers are the classic Riviera pairing. Tailored wool trousers in charcoal or camel work for a more dressed register. Avoid pairing with black or with heavily patterned bottoms — both fight the softness of the stripe.

How should a pinstripe shirt fit?

A pinstripe shirt should fit close to the body without straining across the chest or shoulders. The shoulder seam should sit on the edge of your shoulder, not below it. The hem should fall just past the belt line — long enough to tuck cleanly, short enough to wear out. Cuffs should sit at the wrist bone, with enough room to roll twice without bunching.

Is a pinstripe shirt formal or casual?

The pinstripe shirt sits in the middle register between the two. Tucked into tailored trousers with the cuffs buttoned, it reads dressed enough for office or evening. Worn open with the sleeves rolled and left untucked, it reads relaxed and Mediterranean. This flexibility is the reason the pinstripe shirt has survived a century of changing menswear.

Can you wear a pinstripe shirt with jeans?

Yes, provided the jeans are the right cut and colour. Straight-leg or slightly relaxed indigo denim in a mid-to-dark wash is the correct pairing. Avoid distressed jeans, black jeans, and skinny cuts — all of them fight the shirt's proportions. Tuck the shirt for structure or leave it out cleanly for a more relaxed register.

What is the difference between a pinstripe shirt and a striped shirt?

A pinstripe shirt has thin, narrow, closely spaced vertical stripes woven into the fabric — the stripes are almost always in a single colour on a white ground. A striped shirt is a broader category that includes wider stripes, multiple colours, and horizontal patterns. All pinstripe shirts are striped shirts, but most striped shirts are not pinstripe shirts.

Are pinstripe shirts in style in 2026?

Yes. The pinstripe shirt has returned to the centre of menswear as part of the broader movement toward quiet luxury, soft tailoring, and Mediterranean aesthetics. After a decade dominated by streetwear and heavy pattern, the industry has moved back toward the restrained, considered pieces that define classic European style — of which the pinstripe shirt is a defining example.

Pinstripe Shirt: History, Style & How to Wear It (2026 Guide) | Anovair