Preppy Dress Shirts

Ranked in order of quality, IME.

New England Shirt Company

Gant

Ralph Lauren (I'll let you find that site)

Rugby

Southern Tide

lacoste
Fred Perry
Ben Sherman

Preppy/Trad Dress Shirt = OCBD.

Everyone else gets in line behind Brooks Brothers, Mercer and J Press.

what about the patterns like stripes or checks? which ones are prep? i have ones from RL that are too casual to be worn with a suit but are stripes. bengal/ pencil/ university stripe/ gingham? i'm not so sure about the terminology.

gant is better now than RL? inneresting. been awhile for me i guess.

The Gant "preppy" button-fronts have been better IME. Most of the preppy/fratty stuff RL makes is hardcore China/Macau stuff. Although most of Gant is made in China as well I have a few vintage shirts of theirs that are still awesome and their new stuff seems to be of higher quality than most of the predictable RL China stuff.

I have a few RLPL "preppy" shirts as well that obviously take the cake, but I assume the OP isn't looking for $400 shirts...

Not sure about rankings, but the recent Gant Rugger OCBDs that I've purchased are great.  They seem to fit my large neck but slimmer torso very well.  Moreover, they don't seem to be too popular as I am seeing them regulalry at significantly discounted prices ($40-ish) in the shops in my area in all sizes, colours and patterns.

 

For a very casual OCBD that fits similarly to the Gant, but without the same length to the shirt, I've bought a couple Canterbury of New Zealand shirts.  They are very thick.  The ones i have, have contrasting inner cuff fabric and a couple other minor details that make them very casual.  I found them at a Marshall's in Canada for about $30 each.  I liked their sturdy rugby shirts back in high school, and these seem to be made in a similar sturdy fashion. 

 

Again, I'd classify both as very casual in appearance, so perhaps not good options as "preppy dress shirts." 

 

Ralph Lauren Purple Label are my choice in this category. Mainly due to fit. They can be had on Ebay under $200 quite easily.

+1. i have 2 purple label ocbd that i love. great fabric

ah thanks for the tip on gant!

Mate I purchased a Canterbury of New Zealand few years ago. The cut was horrible. The leanth+shoulder+sides are slim cut. And the neck way too large. You will have to be a skinny guy with a very thick neck. I paid about $90 for mine was on sale . 5/6 washes the color faded(it was a nice dark grey).

You are right about the fit.  As I hinted at in my comments on the Gant offerings, I have a 17.5 inch neck, but need the body/arms/length of your average 16/16.5 inch neck shirt.  Thus my fondness for the Canterbury in large.  I find its fit to be similar to the current Gant offerings (save the length).  I can't say that I've had any problems with the colour fading.  Mine are a striped blue and white, and a solid blue.  They look the same as when they were purchased 7 or 8 months ago.  I would be hesitant, however, to pay more than $40 or so for them, as I would Gant, Polo, RRL etc..

 

For my body type the cut is excellent.  For those with different neck/torso proportions I'd imagine the fit to be lousy.