The eBay Chronicles #003
Vineyard Vines and General Buyers Guide to Cotton Chinos
An Ode to a Classic
As seems to be the case with much of my time these days, I sit on a train headed south to a warmer climate, which reminds me of my favorite late summer/early fall pair of pants: My secondhand Vineyard Vines chinos. Vineyard Vines has gotten a bad rap in the fashion space as of late for becoming the brand of the fraternity brother and New York Patagonia-vest-wearing investment bankers, but I have always enjoyed their 100 Cotton Chinos which can be found for $20-30 on eBay.
Fit, Feel, and Flexibility
The chinos become soft and plush after being worn in and can be starched back to a stiffer state if that is what you like. The stitching is tight and there is usually a hem at the bottom of the pants. Their Classic Fit is wider and roomier, while the Slim Fit still being roomy by the ankle though slightly tapered by the thigh. For me, I like to roll up my chinos in the warmer months for a little more laid back and comfortable outfit. These chinos allow for that flexibility with plenty of space at the ankle to roll them how you like. From boat shoes to loafers or even boots, chinos are the jack of all trades. Whether you grew up in a sailing town like myself or just want to embrace your inner 35th president, you can’t go wrong. While Vineyard Vines has made some of their more recent offerings less attractive by using cheap materials, their original natural-fiber-made staples have been a stable part of their business like the Tucker Shirt and Breaker Chino.
How to Find the Good Ones (A Buyer’s Guide)
As I have said in some of my previous writings make sure to always check the material composition before purchasing something online. Vineyard Vines has made the original Breaker Chinos increasingly difficult to find and many of their new lines have more of their “On-the-Go” material which is made of a Nylon blend. When searching, look for the 100% cotton versions. in many of the older lines they have their brand label on the back of the garment on the waist placed by the belt loops, as opposed to the newer ones which have them on the inside (Example shown in photos below from a pair of Vineyard Vines Corduroy Pants from a similar era).


The older styles are also usually a more classic fit and less tapered, so always ask sellers about the history of the garment if they know it and if the pants are rough or plush to the touch. In most cases unless they have been re-starched it will take a few washes to get the pants to develop that signature plushness. This is for all cotton chinos and a good rule to follow when buying secondhand. You should be able to drag your nail against the grain without it snagging or stuttering like it would with a corduroy or loose denim. Usually, nylon blends are knitted incredibly tightly and lack an easily discernable grain, which is an easy way to tell the material blend if the label was taken out or cut off. Additionally, a slight shine on the fabric or a zipper-like sound when you brush your nail against it can help you tell if it’s a mixed blend. This method isn’t foolproof, however; be careful, as blends with a very small amount of nylon, typically 1-5%, can be difficult to distinguish from pure cotton.
A Brand Worth a Second Look
Even though Vineyard Vines has fallen a bit from their neo-prep upbringings they do still have some staples worth looking for secondhand. The brand is also true to its New England roots: founded in Martha’s Vineyard, Massachusetts and now headquartered in Stamford, Connecticut, it is still owned by the same brothers who started it. The brand has never received funding from the private equity firms that have killed so many brands, making its survival a nice story to support; even if they have made some sacrifices to stay with the modernist times.






Great review and guide. I hadn't considered VV long pants, not being familiar with their older models. I have about 5-6 pairs of their khaki Club Shorts, which are just excellent, and if you get them "vintage" enough (I don't know, maybe 10 years old or so?), they have nice, albeit fake, mother of pearl buttons, while the newer ones have cheap looking solid white plastic buttons and the fabric is not as good.
Your eBay guides are valuable. This is how I got started on thrifting on eBay, after reading an Ivy-Style article over ten years ago, written by someone in France who buys from the US eBay, and it detailed his learning curve, from clueless to savvy buyer. I also went through this "journey," starting off with being clueless about sizing and fabrics.
By the way, after reading an article like yours, I would normally be on eBay hunting up a couple pairs of VV khakis - but alas, I live in Europe now and the shipping is prohibitive, so for the most part, I'll just have to enjoy my existing collection of clothing.