If you’re one of the many men who identify with traditional preppy casual style, this guide can help. Whether you vote conservative, hunt and play cricket, or just happen to like the overall aesthetic, pulling it off naturally and skilfully requires information you won’t find on the high street.
With its origins in north eastern American university wear, preppy fashion has come to define the United States’ upper and upper-middle classes. It’s also known as Ivy League style: the defining campus uniform of prestigious academic institutions such as Harvard, Princeton and Yale.
The general aesthetic sees an English countryside tailored base built up with sportswear influences from modalities such as equestrian, sailing/yachting, hunting, fencing, rowing, lacrosse, tennis and golf, amongst others.
This is often complemented with tasteful family heirloom jewellery/accessories and exquisitely crafted leather goods (typically constructed from vegetable-tanned leather), with very little room for any ‘eccentricity’ – although lifelong adepts will deny the latter, claiming their one of a kind silver buckle belts or bright orange watch strap spell rebellion with a capital R.
Demystifying Preppy Style
From this restricted academic niche to the international elite, later to reach all market levels, the American Prep look has now gone global. It’s easy to emulate, and, despite controversy, done right, flatters men of all ages and shapes, suits different lifestyles and is widely accepted (have you ever seen a gent in a navy blazer and red chinos not get into a club?).
Ralph Lauren, the world’s most successful ambassador of the style – a man who created arguably the go-to brand for preppy apparel – demystifies its boundaries: “People ask how can a Jewish kid from the Bronx do preppy clothes. Does it have to do with class and money? It has to do with dreams.”
Image: Gant Rugger SS13
Image: Tommy Hilfiger AW13
Image: Tommy Hilfiger AW13
The Key Pieces
While Lisa Birnbach’s 1980 Official Preppy Handbook (recommended reading if this article inspires you to find out more about the subject) hasn’t yet been outdone in humorously analysing prep style, here are ten must-have preppy staples, from which you should be able to build a flawless wardrobe:
- Chinos. Focus on them and forget about jeans. They’re OK in classic khaki and navy, but you can take the concept further if you opt for red, bold greens/blues or yellow. Extra bright, unusual colours or even neon shades are the statement, ‘extra mile’ alternatives that will set you apart.
- Polo Shirts. Mostly those featuring prestigious branding (usually a stylised animal). They also come with random numbers, references to polo (the sport), or in thicker, long-sleeved rugby tops.
- Navy Blazers. Often complete with brass buttons and embroidered crests. They’ll dress anything up, but remain relaxed and easy to wear. From shorts to tailored trousers, they go with anything. To summarise: until you get the navy blazer, you don’t have the look sorted.
- Sweatshirts. The casual sportswear alternative to your classic crew neck jumpers. Typical ‘jock’ uniform. Wear it as a t-shirt with nothing underneath or over an Oxford shirt to make it more modern.
- Brogues/Penny Loafers. Go for rich browns or oxblood if you’re doing full-on trad. Thick soles, printed leather and contrast-laced versions are available if you feel like making more of a statement. They can both be worn sockless with turned up or slightly shorter trousers during spring/summer.
- Tweed Tailoring. Traditional Edwardian leisure attire and signifier of English outdoors elegance. Today, the association is the same, and this British speciality finishes off a preppy getup with class. If the fit is right (slim but not restrictive), your tweed will look sharp while remaining comfortable and practical to wear, particularly during autumn/winter.
- Boat Shoes. Wear during summer, preferably sockless, although many tend to combine with bright socks in winter too.
- Casual Ties. Diagonally striped or with small embroidery; woollen or knitted; bow or neck – no matter what style you go for, they should be worn in a smart-casual manner with chinos, sports coats, shirts and jumpers/sweatshirts.
- Cricket Jumpers. The classic white/cream, deep V-style or simplified versions thereof. Even if you don’t know the rules of the game, give them a go.
- Belts. Woven, elastic or vegetable-tanned leather belts, complete with brass buckles, sometimes lined in silk – the belt is possibly the most imaginative accessory in the prep world. Needless to say, we’re not talking studs or anything in widths lower than 25mm or higher than 35mm.
These ten essentials will set you well on your way to nailing traditional American Prep style, but it’s important to build on this capsule wardrobe foundation with more individual choices:
- Dockers Alpha Khaki Chinos Straight Fit
- Mercer Regular Fit Chino
- Acne Studios Max Satin Slim-fit Cotton-blend Trousers
- Ian Slim Fit Polo
- Polo Ralph Lauren Polo With Cross Embroidery
- Wesc Homerun Crew Sweatshirt
- Polo Ralph Lauren Striped Cotton-jersey Polo Shirt
- J. Crew Ludlow Club Blazer With Center Vent In Italian Wool
- J. Crew Ludlow Fielding Sportcoat In Harris Tweed Wool
- Richard James Harris-tweed Shirt Jacket 215133
- Cream Cricket Jumper
- J. Crew English Silk Tie In Kenya Stripe
- Hammond & Co Designer Navy Mallard Tie
- Ralph Lauren Braided Belt
- Ralph Lauren Silk-tie Leather Belt
- Grenson Sid Burnished-leather Longwing Brogues
- Topman Bass Weejuns Burgundy Larson Loafers
- Sebago Schooner Leather Boat Shoes Brown
The Dos & Don’ts Of Preppy
- If anyone can do it, you have to do it differently. You don’t want to end up looking like a catalogue page. We strongly encourage you to find spectacles that set you apart, a watch that offsets your attire, an unusual scarf – basically anything you can think of that doesn’t make you disappear in the crowd (we’ve already said it, and will repeat: this look is easy to emulate).
- Fake vintage is bad. Keep clear of off-the-rack, pre-aged leathers or metals, distressed chinos and canvas bags. Explore your nearest vintage shop or browse eBay and find yourself a unique piece. You don’t want to hit the pub and bump into another chap rocking the same khakis with the exact same amended hole on the knee. This rules extends to diamante (costume) cuff links, fake watches and family crest rings.
- Be the class rebel. Such a conformist dress code must have its rule breaking accents. Ever considered cutting off the collar of your polo/rugby top and turning it into a Henley? Likewise, changing the buttons on your blazer/chinos or switching the laces on your shoes are easy alterations that anyone can make.
- You have to splurge on a certain level of quality, so beware of budget alternatives. For instance, cheap-looking bright green chinos will jar with an authentic tweed jacket.
- Should I pop my polo shirt collar? You can, if you’re on holiday, on a yacht, desperately trying to avoid burning your neck. Otherwise, your collar should be down, buddy.
- Don’t ever try to get into character just because you bought the clothes. Dressing the dream is one thing. Don’t let the look take over your personality with fake public school accents, tasting drinks you don’t like or sneering at your mates who stuck with their jeans and three-for-two deal shirts.
- Don’t EVER wear a sweatshirt or a t-shirt from a school you didn’t go to. You’ll get asked about it immediately and embarrass yourself. This rules extends to crests, coats of arms, mugs, bumper stickers and fridge magnets.
- Be coherent. Don’t adopt sailing attire if you can’t swim, don’t sport a polo player on a horse logo larger than 2cm-high if you feel queasy with the smell of stables, and don’t try to pull off a hunting jacket if you’re a veggie.
- Prioritise functionality. You’ll find these casual clothes are typically made from standard materials like heavyweight cotton and wool. This means that despite the high price tags, they aren’t outrageously expensive items of clothing to invest in, because they’re designed to perform and built to last. Think twice before opting for overly-fine wool, delicate suede or camel hair.
- Need to justify the style? To quote Ms. Birnbach: “Prep clothes are sensible: rain clothes keep you dry; winter clothes keep you warm; collars are buttoned down so they don’t flap in your face when you’re playing polo. Layering is a natural response to varying weather conditions.” You see – practical AND stylish.
But now we want to hear what you think: how do you feel about preppy style? Is it worth it when it’s just for the look? How do you interpret it?
Let us know in the comments section below…