East Coast Prep with a Twist feat. F.E. Castleberry

December 5th, 2011

I have to admit, I don’t read many other blogs. Once I’m finished with everything it takes to manage and expand TheStyleBlogger, it’s usually time to shut my computer.

Ever since Jenilee introduced me to Unabashedly Prep, however, I’ve enjoyed watching F.E. Castleberry carve a niche by documenting the East Coast Prep subculture while strategically bending, but not breaking, it’s strongly rooted traditions.

As a fashion photographer turned style blogger, F.E. has an equally great eye behind the camera as he does for putting together outfits that are in-line with the traditional prep aesthetic but carefully updated for a modern appeal.

Here, Fred gives us a taste of some of the layered looks he’s wearing this Fall.

1. Tailored Sportswear

“While a down vest is easily  imagined over a flannel shirt or a Norwegian sweater, I began wearing mine over my sport coats after seeing some Italian do it last year. My style is heavily rooted in American sportswear, thus the tailored clothing/sportswear contrast feels good to me.”

“My vintage Omega Seamaster wristwatch is my favorite piece in my wardrobe.  I wear it everyday. In the spring/summer I pair it with colorful striped nylon bands while in the fall/winter I keep it grounded with a dark brown alligator strap.”


Khaki Cotton Trouser

  • Navy down vest by Penfield ·
  • Brown leather wingtips by Vintage Cole Hann ·
  • Tortoise eyeglasses by Lookmatic ·
  • Navy/yellow striped socks by Norman Hilton ·
  • Red/green striped tie by Brooks Brothers ·
  • Pink stripe oxford shirt by Taylor Stitch ·
  • Watch Vintage Omega Seamaster
  • · Khaki chinos by Club Monaco

2. Do it Yourself

“These chinos could be considered controversial.  They are a nod to my artistic youth and Jackson Pollack during his years in the Hamptons. He splattered huge canvases laid out on the floor of this barn. You either get them or you don’t.  While you can’t wear them too often, I know I’m the only guy doing so when I do.”

“I like to play with textures, patterns, and fabrics.  Here, that attitude is personified with denim, cotton, tweed, silk, tartan, and sterling silver.”


Khaki Cotton Trouser

3. Old World Casual

“Even when I’m casual, I’m not too casual.  I have a tendency to mix casual wear with suiting/sportcoats and dress with a wink and a smile.  This look is a variation on my sport coat/jeans uniform. The wool tartan belt hits its stride when it’s not competing with any other pattern.”

“While I don’t wear slippers outside too often, when I do around the holidays, my monogrammed slippers start more conversations than I seem to anticipate. Great ice breaker at holiday mixers.”


Blue USA Oxford Shirt

  • Navy polka dot pocket square ·
  • Grey cable knit crewneck sweater by Ralph Lauren ·
  • Tan corduroy jacket by Rugby ·
  • Tartan plaid wool d-ring belt by Ralph Lauren ·
  • Tortoise eyeglasses by Lookmatic ·
  • Raw selvedge denim by Rugby ·
  • Navy monogrammed slippers by Del Toro
  • · Light blue oxford shirt by Rugby

4. Straight East Coastin’

“Ribbon belt (and orange at that) with a suit? It just reiterates I don’t take myself too seriously even in dark navy/gray tones. And yes”¦if the leaves are still in the trees, my ankles are still feeling the breeze.”


Donegal Tweed Suit in Monochrome

  • Navy trench coat by Club Monaco ·
  • Blue bengal stripe shirt by Ascot Chang ·
  • Navy polka dot silk knit tie by Brooks Brothers ·
  • Brown double monk strap shoes by Ralph Lauren ·
  • Orange stripe ribbon belt by Ralph Lauren ·
  • Navy waxed cotton weekend duffle by Ernest Alexander ·
  • Tortoise eyeglasses by Lookmatic
  • · Grey flannel suit by Rugby

Thanks, as always, for reading – and special thanks to F.E. for participating.

Yours in style,

Dan Trepanier


Photography by Michael Norwood.