Lookbook

Striped Oxford Shirts: Relaxed Collegiate Drape & Style

Classic Bengal stripe and university-striped Oxford cloth button-downs worn untucked or half-tucked with wide-leg trousers, navy blazers, and boat shoes. A relaxed modern take on timeless Ivy League collegiate shirting.

Casual FridayWeekendSmart CasualOld MoneyIvy LeaguePrepPolishedRelaxedClean-CutSpringSummerTransitionalMid-Range
Tan Cotton Trench Coat with Striped Rugby Shirt and Straight JeansFrom $159

Tan Cotton Trench Coat with Striped Rugby Shirt and Straight Jeans

Oct 18, 2026

Blue and White Striped Poplin Shirt with Wide Leg Charcoal Wool PantsFrom $51

Blue and White Striped Poplin Shirt with Wide Leg Charcoal Wool Pants

Oct 17, 2026

Blue Striped Popover Shirt With Khaki Chino Shorts and Brown Boat ShoesFrom $122

Blue Striped Popover Shirt With Khaki Chino Shorts and Brown Boat Shoes

Oct 16, 2026

Classic Ivy League Striped Shirt with Cream Cable Sweater and Khakis LookFrom $118

Classic Ivy League Striped Shirt with Cream Cable Sweater and Khakis Look

Oct 14, 2026

Shop pieces for these looks

Look 1Men's Tan Single Breasted Trench Coat
Runcati Mens Trench Coat Double Breasted Notch Lapel Slim Fit Long Overcoat
$46.98
Amazon
Look 2Men's Blue White Striped Cotton Shirt
Wide Striped T Shirt for Men Sailor Tee Red White Black Navy Stripes Top Basic
$17.99
Amazon
Look 3Men's Blue Striped Cotton Popover Shirt
Runcati Mens Short Sleeve T-Shirts Striped Casual Fashion Tees Tops
$12.99
Amazon
Look 4Men's Navy Striped Long Sleeve Shirt
OEKO-TEX STANDARD 100 Amazon Essentials Men's Regular-Fit Crewneck Long-Sleeve T-Shirt, Casual Cotton Jersey
$16.00
Amazon
Ivy League Striped Long Sleeve Shirt with Draped Sweater and Chinos LookFrom $149

Ivy League Striped Long Sleeve Shirt with Draped Sweater and Chinos Look

Oct 14, 2026

Classic Country Club White Cable Knit Cricket Sweater and Flannel LookFrom $131

Classic Country Club White Cable Knit Cricket Sweater and Flannel Look

Oct 14, 2026

Green Striped Rugby Shirt Tan Pleated Chino Pants and Penny LoafersFrom $207

Green Striped Rugby Shirt Tan Pleated Chino Pants and Penny Loafers

Oct 12, 2026

Navy Burgundy Striped Rugby Shirt and Camel Pleated Dress Pants OutfitFrom $220

Navy Burgundy Striped Rugby Shirt and Camel Pleated Dress Pants Outfit

Oct 12, 2026

Shop pieces for these looks

Look 5Men's Grey Cable Knit Sweater
JMIERR Mens Cable Knit Crewneck Sweater Casual Long Sleeve Pullover Tops
$19.98
Amazon
Look 6Men's White Cable Knit Cricket Sweater
HOTake Men's Casual Textured Crewneck Pullover Sweaters
$27.99
Amazon
Look 7Men's Green Navy Striped Rugby Shirt
Mens Polo Shirts Striped Cotton Moisture Wicking Classic Collared Casual Golf Shirts for Men
$32.98
Amazon
Look 8Men's Navy Burgundy Striped Rugby Shirt
Mens Polo Shirts Striped Cotton Moisture Wicking Classic Collared Casual Golf Shirts for Men
$32.98
Amazon
Classic Ivy League Navy Blazer with Repp Stripe Silk Tie and Khaki Chinos LookFrom $210

Classic Ivy League Navy Blazer with Repp Stripe Silk Tie and Khaki Chinos Look

Oct 9, 2026

Tokyo City Boy Oversized Beige Mac Coat with Striped Oxford Shirt and Lug Penny LoafersFrom $120

Tokyo City Boy Oversized Beige Mac Coat with Striped Oxford Shirt and Lug Penny Loafers

Oct 9, 2026

Shop pieces for these looks

Look 9Men's Navy Wool Blazer Gold Brass Buttons
Gioberti Men's Formal Single Breasted Blazer Jacket
$54.99
Amazon
Look 10Men's Oversized Beige Mac Coat
Boxy Oversized Trench Coat
$19.86
Amazon

We built this collection to demonstrate how a classic striped Oxford or poplin shirt can feel thoroughly modern when worn with generous drape. Moving beyond rigid office uniforms, bold vertical stripes elongate the torso while the button-down collar rolls cleanly without a tie. We love leaving the top two buttons open and the sleeves loosely pushed to the elbow, grounding the look with pleated chinos or wide-leg wool trousers.

— The Editors

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