Ivy league fashion since the 50s: The 10 iconic staples that never went out of style.

Then: In the 1950s, the navy blazer was the Ivy Leaguer’s armor—single-breasted, gold-buttoned, and cut from wool for a structured yet relaxed fit. Tweed or herringbone sport coats, often with elbow patches, added a professorial edge. Worn over Oxford shirts for classes or dinners, they were versatile enough for a lecture or a date at the soda fountain.

Now: In 2025, the navy blazer remains a style MVP, with brands like J.Crew and Thom Browne offering slim-fit versions in wool or blended fabrics. Tweed jackets, seen at Ralph Lauren, pair with jeans for a modern twist. The fit is slimmer, but the vibe—polished yet approachable—still screams Ivy League. Wear it to a job interview or a coffee shop debate; it’s your academic superpower.

Then: The OCBD, pioneered by Brooks Brothers, was the 1950s campus uniform. Made of crisp cotton Oxford cloth, its button-down collar kept things tidy without being fussy. Worn slightly loose, often untucked for that “I studied all night” nonchalance, it was the backbone of every outfit.

Now: Today, the OCBD is still king, with Uniqlo and Everlane offering tailored cuts in breathable cotton. Available in white, blue, or subtle patterns, it’s as at home under a blazer as it is with chinos for a Zoom class. The collar roll? Still a flex, signaling you know your Ivy League history.

Then: Grey flannel trousers were the 1950s answer to stiff dress pants. Cut from soft, warm wool flannel, they had a relaxed fit with pleats, perfect for striding across campus in fall. Paired with blazers or sweaters, they were the epitome of understated class.

Now: In 2025, flannel trousers are back, with Bonobos and Banana Republic offering slim, flat-front versions. Still wool, sometimes blended for stretch, they’re versatile enough for a boardroom or a bar. The grey hue remains a neutral canvas, keeping the Ivy League polish alive.

Then: Borrowed from military uniforms, khaki chinos were the 1950s Ivy Leaguer’s casual rebellion. Made of durable cotton twill, their straight cut offered comfort without sacrificing sharpness. Rolled cuffs and a slightly wrinkled vibe said, “I’m studious, not stuffy.”

Now: Chinos are a 2025 wardrobe staple, with brands like Dockers and Loro Piana offering slim or relaxed fits in cotton or cotton-blend fabrics. Worn with loafers or sneakers, they bridge the gap between campus and corporate, keeping that Ivy League ease.

Image source: He spoke Style.

Then: The varsity jacket, with its wool body and leather sleeves, was the 1950s jock’s pride. Embroidered with school letters, it was worn by athletes and wannabes alike, layered over sweaters for chilly game days. It screamed school spirit with a side of swagger.

Now: In 2025, varsity jackets are a streetwear darling, with Golden Goose and Supreme riffing on the wool-leather combo. Modern fits are boxier, often paired with hoodies or jeans, but the collegiate vibe—complete with embroidered patches—keeps the Ivy League legacy alive.

Then: Wool sweaters, in V-neck or crewneck styles, were 1950s layering essentials. Knit from merino or Shetland wool, they were warm, slightly boxy, and perfect over an OCBD for a cozy yet sharp look during New England winters.

Now: Brands like J.Press and LL Bean keep the wool sweater game strong in 2025. Slimmer cuts and softer wools make them versatile for layering or wearing solo. The V-neck’s tie-revealing charm and the crewneck’s clean lines still radiate Ivy League warmth.

Then: The sweater vest, often in solid colors or subtle patterns, was a 1950s favorite for its lightweight warmth. Worn over an OCBD and under a blazer, it added a scholarly touch without overheating in lecture halls.

Now: In 2025, sweater vests are having a moment, with Gucci and Zara offering fitted wool or cotton-blend versions. Worn alone over a shirt or layered under a jacket, they’re a nod to the Ivy League’s geek-chic roots, perfect for a modern campus vibe.

Then: The repp tie, with its bold diagonal stripes in silk, was the 1950s Ivy Leaguer’s way of saying, “I’m in the club.” Worn with a slightly loose knot, it added color and school pride to blazers and OCBDs.

Now: Brooks Brothers and Ralph Lauren keep repp ties alive in 2025, with slimmer widths and vibrant stripes. They’re still the go-to for adding a pop of Ivy League flair to suits or casual sweater looks, tying you to tradition.

Then: G.H. Bass’s Weejuns penny loafers, crafted from polished leather with a moccasin toe, were 1950s campus royalty. Worn sockless or with argyle socks, their “penny” slot was pure Ivy League folklore—practical yet playful.

Now: Loafers are a 2025 staple, with Alden and Tod’s offering sleek leather or suede versions. Worn with chinos or suits, they’re the ultimate Ivy League shoe, blending comfort with a wink to heritage.

Then: Argyle socks, with their diamond patterns in bold colors, were the 1950s Ivy Leaguer’s subtle flex. Made of cotton or wool, they peeked out from loafers or brogues, adding personality to otherwise restrained outfits.

Now: In 2025, argyle socks from brands like Happy Socks and Paul Smith are a playful nod to the past. Worn with cropped chinos or suits, they keep the Ivy League’s quirky charm alive, proving small details pack a punch.