Six Preppy Outfit Ideas for Men, From Classic and Tweed to Tennis and Nautical

The foundation of a preppy wardrobe is a navy blazer, an Oxford cloth button-down (OCBD) shirt, khaki chinos and penny loafers.

Start with a navy blazer that fits well at the shoulders, for example from Brooks Brothers or J. Press, two American clothiers long linked with the look.

Pair it with a white or light blue OCBD shirt, for example from Gitman Vintage or Mercer & Sons, and khaki chinos, for example from Bills Khakis.

For summer, swap the chinos for faded red Nantucket Red shorts or trousers.

Nantucket Reds are made from a cotton canvas that starts brick red and fades towards dusty pink with washing and sun.

Murray’s Toggery Shop on Nantucket introduced them in the 1960s, and the shop still sells them under the Nantucket Reds name.

Complete the outfit with brown penny loafers, for example from Alden or G.H. Bass Weejuns, a leather D-ring belt, for example from Smathers & Branson, and a simple watch, for example from Timex.

Wear: navy blazer, white or light blue Oxford button-down shirt, khaki chinos, brown penny loafers.

For the academic side of preppy dressing, start with a tweed sports jacket in herringbone or houndstooth, in a muted colour such as olive or rust.

A jacket in Harris Tweed, a protected cloth handwoven in the Outer Hebrides, is one option, sold by many makers including J. Press.

Layer it over a button-down shirt in pale pink or light blue, for example from Kamakura Shirts or Proper Cloth.

Pair it with dark brown corduroy trousers, for example from Orvis or Peter Millar, cuffed at the ankle to show colourful socks, for example from Happy Socks or Pantherella.

Corduroy is hard-wearing and comfortable, and its ridged texture sits well beside the rougher surface of tweed.

Complete the look with suede Oxford shoes, for example from Allen Edmonds, a silk pocket square, for example from Drake’s, a watch on a leather strap and tortoiseshell glasses.

Wear: tweed sports jacket, pale pink Oxford shirt, dark brown corduroy trousers, brown suede Oxford shoes.

Country sports have long been linked with traditional dressing, and this outfit draws on the British countryside clothes of the Sloane Ranger style and the wider story told in our guide to preppy origins.

Start with corduroy trousers in forest green or burgundy; trousers made for hunting, for example from the Danish maker Laksen, often add reinforced knees and seat and extra pockets for outdoor wear.

Pair the trousers with a tattersall check shirt, for example from Ralph Lauren, in a pattern of thin crossing lines, and a cashmere or wool tie, for example from Drake’s.

Layer a merino wool sweater vest, for example from J. Press or Brooks Brothers, over the shirt for warmth.

Complete the look with Wellington boots, for example from Hunter, a waxed cotton jacket, for example from Barbour or Belstaff, and a flat cap, for example from Lock & Co. Hatters.

Leather gloves, for example from Hestra, a paisley pocket square and a simple field watch, for example from Hamilton, finish the outfit.

A small vintage-style pin with a country motif, such as a pheasant or a retriever, is optional.

For more country outfits, see our equestrian style outfit ideas and our list of heritage designer brands.

Wear: tattersall shirt and tie, merino sweater vest, waxed cotton jacket, green or burgundy corduroy trousers, Wellington boots.

Preppy style has strong ties to tennis, and this outfit suits a country club afternoon.

Start with white tennis shorts, for example from Lacoste or Fred Perry, two labels with tennis roots.

Pair them with a polo shirt in a bold colour such as kelly green or royal blue.

Layer a cable-knit tennis jumper over the polo: the V-neck shows the polo collar, the cable knit adds texture, and contrasting stripes at the neck or cuffs give the sporty look.

Complete the look with white tennis trainers, such as Adidas Stan Smith, Fred Perry B721 or Tretorn Nylite, and sunglasses, for example from Persol or Ray-Ban.

If you are playing, check the club’s rules on court clothing, which often ask for white, and add white wristbands if you like.

A needlepoint belt with a tennis motif is a playful extra with trousers off court.

Wear: polo shirt, cable-knit tennis jumper, white tennis shorts, white trainers.

Preppy style also borrows from sailing, and this outfit suits a summer day by the water or a Southern preppy summer.

Start with faded red shorts, such as the Nantucket Reds sold by Murray’s Toggery Shop.

Pair them with a navy and white striped Breton shirt, for example from the French makers Saint James or Armor Lux; the striped top began as French naval wear.

Add brown leather boat shoes, for example from Sperry, whose rubber soles were designed to grip wet decks, and a braided rope bracelet if you like.

Finish with a cap, for example from Vineyard Vines or Southern Tide, square sunglasses and a water-resistant diving watch, for example from Bremont.

Wear: navy and white Breton shirt, faded red shorts, brown boat shoes.

For a casual weekend look, start with dark, straight-leg jeans, for example from Gant, rolled once or twice at the hem.

A dark wash looks smarter than a light one, and a straight leg sits well with the other classic garments.

Pair the jeans with a striped rugby shirt, for example from Drake’s or Rowing Blazers, in navy and white, green and gold, or navy and yellow.

Layer a cardigan, for example from Ralph Lauren, over the rugby shirt for warmth.

Add canvas trainers, such as Converse Jack Purcell or Superga 2750, and a baseball cap, for example from Ebbets Field Flannels, or a knit beanie.

Wear: rugby shirt, navy cardigan, dark straight-leg jeans, white canvas trainers.