Get Preppy

Craig of That Dapper Chap shows us how to achieve the preppy style and stay on trend this summer.

One trend that I’ve spotted coming through stronger and stronger in the spring summer collections is the preppy style. While big brands like J Crew, Tommy Hilfiger and Ralph Lauren have been champions of this style for years, it’s becoming more mainstream, so I wanted to give you a little insight in to how you can achieve one of this summers key looks.


The preppy look has a few key tops.

First up, shirts: The button down Oxford shirt is a staple. Choose your Oxford shirt in top preppy colours like pink, yellow and green which are great colour options, but pale blue and white work well too. A gingham print shirt is another strong option, either in a small or large check.

Looking at sport for inspiration, two tops favoured by the preppy guy are the rugby shirt and the polo shirt, again colours are important and feel free to go plain or all out striped.

Preppy knitwear: college cardigan, fairisle sweater, Cricket jumper and a striped cardigan

Next we have sweaters. The fine knit crew or V neck is a perfect addition for the warmer months and can be worn draped over the shoulders. In cooler months the cricket sweater is the sweater of choice, with it’s cable knit and coloured V neck and cuff trims. Alternatively an argyle or fairisle sweater works really well too.

The Gunn & Moore Cricket Sweaters

Cardigans work well, particularly the type with a contrasting edge, or a college style cardigan with a badge or letter applique, as do Rugby tops which are yet another key item for the preppy look.

Rugby tops are a good staple item for a real preppy look. Feel free to wear over a shirt and bow tie

Lastly no preppy guy would be without a single breasted navy blazer or a subtle striped seersucker blazer. That’s great for the warmer months, but in winter switch for a tweed or heavy wool blazer. You’ll elevate the look even further if there’s a college style badge stitched on the breast.

Preppy jackets: A brown tweed blazer, striped seersucker and classic navy


The top trousers for a preppy look are chinos. Classic navy is great but don’t shy away from white, yellow, red or green either! Chinos with embroidered embellishments like anchors or fish, fit this look really well too. ¬†Feel free to roll the cuffs up and make sure you include a belt.

When it’s warm opt for chino shorts, again colour is important, as are those embroidered details.

Winter requires a heavier fabric, so choose something in wool, tweed or corduroy. Checks are good and work well.

Preppy pants: Tweed trousers, red chinos, cords, embroidered chinos, green chinos


Footwear is focused on the classic tan leather brogue, the loafer and the boat shoe, depending on the occasion. Feel free to lose the socks as this works well for the preppy look, but on those days that require a little warmth at the ankles go for plain cotton socks in a bright colour.

Shoes: penny loafers, boat shoes and classic tan brogues all from Next
A preppy look created with a navy blazer, chinos and brogues with pink socks and tie



It’s the accessories that really pull the preppy look together. Bow ties are essential. Go for something striped or nautical, the same is true for neck ties too. The two bow ties below are from J Crew are are just perfect. If you prefer a neck tie you should also consider a club tie which has small emblems all over it.


Other must have accessories are sunglasses, striped scarves worn loosely around the neck, nautical anchor bracelets, and a watch with a Nato band that can be changed to suit whatever colours you may be wearing on any particular day. The Daniel Wellington watch is a good example of this.

Accessories make the look: Striped scarf, pink socks, preppy watch with nato band, plaited belt and anchor bracelet

Another great accessory, and somewhere to pack your laptop, note book and that copy of your favourite magazine is a great bag. It has to be a satchel style of course as it suits the look. The three below are from Hydestyle, Niche Lane and The Cambridge Satchel Company.

A selection of perfectly preppy ties from

I hope this post has given you an insight on how you can achieve your own preppy look. When you create you own look please tag me on social media and feel free to leave me a comment here to let me know your thoughts.

My own preppy look photographed by PhotoByIan

Leave a Reply


  1. April 20, 2018 / 7:14 am

    Very trendy looks I like the styles and all the accessories are also very trendy. Thanks for sharing

    • craig
      April 22, 2018 / 1:25 pm

      Thanks very much!

  2. June 12, 2018 / 9:47 am

    All the models are looking perfect. The accessories are beautiful. I like the bags specially.