Preparatory Style

What is preparatory style? (Definition here.)

Preparatory style is something I have admired for a long time. I guess the reason I like it is because it’s so far removed from the way that I normally attire myself, but because it has such strong elements, I really respect it for what it is. When I was at school, I was forced to dress in a preppy style (white collared shirt, green tie, green kilt, black stockings, black shoes, green blazer), & even though I often rebelled against having to constantly tuck in my shirt, I kind of liked the simplicity of the look too.

There are a lot of people who look preppy but also dull. Turning you into a conservative clone is not the aim of this article! I think it is super important, regardless of the style in which you dress, to imbue your look with personal touches & striking individuality.

Let’s get one thing straight — done well, the prep look is incredibly hot. Healthy, athletic-looking people clad in perfectly-fitting natural fibres, like cotton, wool & leather, is really hard to beat. It’s also a very easy way to look chic & polished.

Essential elements

For anyone of either sex going for a preppy aesthetic, the following items are essential: Crisp collared shirts, v-neck cashmere sweaters, lace-up oxfords, scarves, vests for all occasions, classic sunglasses, a trenchcoat, riding boots (Frye do the best ones) & polo t-shirts. You could also carry a tennis racquet for bonus points. Another bonus point for oxfords in patent leather.

Girls, as usual, have a few more additional extras. Try experimenting with headbands, patterned legwear, skirts with pleats, well-fitted dresses, pearls, charm bracelets & cubic zirconia stud earrings (diamonds are so gauche).

Usually most prep dressing stays within a pretty plain palette — black, white, navy, red, grey. If you’re buying basics to supplement this look, it’s best to stick within these colours, & then if you want to don a yellow blazer or royal blue kilt, you’ll find that it probably goes quite well with the rest of your wardrobe.

Stripes are the preparatory holy grail. They are perfect. To do the look well, you should own at least one striped shirt or sweater, & a pinstriped vest, blazer or suit jacket. Argyle, polka dots, tweed & tartan all have their place as well. Preps also love emblems & crests. You can go totally nuts with this — they’re so cool, I just adore them.

It’s also important to have a great stock of basic items, like plain v-neck t-shirts, racerback singlets & collared t-shirts. (American Apparel is my favourite place for these.)

How to do it

One thing that sets prep style apart from other ways of dress is that things tend to be immaculately fitted to the body. If you’re going to rock this look, it is really really important that you buy clothing which is the right size for you. As well as the standard criteria of buying things which fit — look in a mirror; make sure you can move around in your clothing; check lengths; be sure that your clothing skims your body rather than clinging to it — you also need to think about layering. Preps love to layer! It is not uncommon to wear a shirt & a vest & a cardigan & a blazer, as well as a scarf. When you buy items like this, you need to consider what is likely to be worn under or over them. Make sure your vest will fit a shirt beneath it, for example. Buy a blazer with a bit of extra room so that you can wear it with a sweater. You get the idea. (More information on layering at How To Wear Layers Without Looking Like A Crazy Bag Lady!)

Just as the cut is important, so is the quality of what you’re buying. Don’t be tempted to buy 3 wool sweaters for $50 each — save your money & buy one which is fantastic quality but twice the price. It will pay for itself. You’ll get much more wear out of it, & it will look good for a lot longer than something cheaper. Even though these days we can buy clothing for a pittance, you truly do get what you pay for.

For girly prep style, it is hard to go past a good dress — one that fits you well — or a skirt with pleats. When I say a dress that fits you well, I mean something which draws attention to your best assets & skims over your flaws. By the way, to do prep style properly, drawing attention to your best assets does not mean major cleavage. Make the focus your neck, collarbone, forearms or legs. Choose one thing & showcase it. Don’t let it all hang out!

Putting together a preppy look is quite easy. Take a plain white v-neck t-shirt & match it with a pleated skirt. That’s your basic outfit, but then you can mix it up quite a lot. Throw a cardigan over the top. Wear knee-length socks & wingtip shoes or platform mary janes. Carry a pvc satchel & wear amazing glasses. Pull your hair up into a chignon & secure it with a brightly-coloured ribbon. Wear a stack of bracelets on one arm, or a silk scarf knotted around your neck. Accessories are the way to ensure your preppy look isn’t boring or stale.

Another way of mixing it up is to make one element slightly unusual. For example, if you’re a boy wearing a crisp shirt & v-neck cashmere sweater, instead of donning the standard khakis that would normally go with this look, you could try wearing long skinny jeans in a plain wash — like black. Or you could wear shorts that fall to the knee with a pair of slip-on trainers (Vans, for example). Don a fedora & you’re ready to go.

Some people feel really constricted & boring in a collared shirt. I understand, I feel the same way! Allow yourself to wear it in a relaxed manner — leave the top couple of buttons undone & always, always, always roll up the cuffs! Forearms are sexy, okay?

Putting it into practice

Here are some great pieces I’ve found online which will help you embrace the prep look!


Left to right: Moschino Cheap & Chic Quilted Applique Heart Gloves; Marc Jacobs button detail boots; Karen Walker Super Speed sunglasses; Ralph Lauren Large Stirrup Bracelet; Silk Lace Printed Scarf; Grandpa’s Pocket Watch Necklace; Oscar de la Renta Larrabe Frame Bag; Lux Lili Tuxedo Bomber; Sweater Earwarmers; Fedora Hat; Small Satchel Bag With Buckle; Tiffany & Co. Return to Tiffany Heart Tag Bracelet.

Ralph Lauren men

Left to right: Ralph Lauren Luxury Shetland Wool Crewneck (I love this in the power blue they have on the model. I wish more men would wear this colour! It is totally orgasmic!); Ralph Lauren Cashmere Jersey V-Neck; Ralph Lauren Lambswool Half-Zip Pullover. P.S. I don’t recommend tucking your trousers into your boots. I think it is a bit naff.

Ralph Lauren women

Left to right: Ralph Lauren Martine Long-Sleeved Shirt; Ralph Lauren Big Pony Mesh Dress; Ralph Lauren Adrianne rugby dress.

All of these pieces from Ralph Lauren would make excellent cornerstones of your preppy wardrobe. The styling above is a bit staid, but imagine, for example, the R.L. Martine Long-Sleeved Shirt with a pair of shorts or a skirt & Frye Engineer Lace-Up Boots! Yum.

When it comes to restyling the traditional prep look, your imagination & courageous spirit are your best assets. Well, that & your Visa! Try new things, especially if you think they won’t work — you never know, you could strike aesthetic gold!

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