At my favorite thrift store again tonight (Unique in Riverdale, NY), I found several items that I thought worth showing. L to R: Nautical belt from Leather Man Limited in Essex, CT ($6.99), navy surcingle belt from Dockers ($4.99)…not a preppy brand per se, but passable, dirty bucks with brick red soles from Bass ($12.99), crew neck heavy wool sweater from L.L. Bean (19.99), no name white 100% cotton scarf ($3.99) and a pair of no name 100% cotton, plain front khakis embroidered with whales ($12.99)…though I thought the whale motif just a bit too large. Total cost of all items: $66.94. My guess is that these items would retail for around $300. So what items did I buy? I got the L.L. Bean sweater. It was a large and a perfect fit, made in the USA of 85% wool and 15% nylon for strength. It will be great for winter. I also got the navy surcingle belt. Again, a perfect fit. The nautical belt from Leather Man was such a great find, but not the right size. It was the third belt from that maker I’ve come across in the last month. The Bass shoes were unfortunately 1/2 size too small. The embroidered khakis were not my size either. I passed on the sarf. The shots for this trip were taken inside the thrift store under fluorescent lights (please excuse).
The workmanship on the Leather Man belts always seems of the highest quality, and I wouldn’t mind making a trip to their factory/store. It’s about 90 minutes from where I live.
I’ve been looking for a while now for a pair of dirty bucks, but I can never seem to find them in the right size. I wear an 11 and these were 10 1/2. They were in especially good condition, which is rare for thrift store shoes. One guy in the store tonight had found two pairs of perfectly fitting canvas Sperry Topsiders. Most of the time I buy my shoes at factory outlet malls (Sperry, L.L. Bean, Bass and Cole Haan all have stores at a nearby outlet). I’ve also found leather Topsiders, Clark’s Desert Boots and Cole Haan leather, cap toe dress shoes for 50% off at Marshall’s.
Follow Up Note: All of the items that I did not buy on this trip were GONE the next day.
Thrift Store Preppy 
i thrift all my clothing pretty much but my boyfriend doesn’t reallyyyyy enjoy going so i have no experience in men’s clothing. wish i did! i do however have lots of experience with preppy clothing. i grew up in baltimore, md. doesn’t get much more preppy than that haha
It’s amazing what clothes you can find thrifting. People will donate practically brand new items — with no identifiable flaws – because it’s a tax write-off. I would rather get something in a thrift store than pay retail any day. I can’t tell you the last time I walked into a preppy store like Brooks Brothers and paid full price. I stopped doing that when I started seeing their merchandise on the thrift racks.
By the way: any thrift stores in Baltimore you’d recommend? I’d be glad to list them. (But you might not want the secret to get out). 🙂
it’s so great to hear that because one of the biggest issues with dressing preppy is that the brands are so damn expensive. i mean, just incredibly expensive. and then that can lead to assumptions about preppy people-they’re snobby, rich, stuck up, whatever. i love that you’re breaking up those assumptions! i’m actually living in LA right now (where hipster style predominates) but in baltimore value village thrift has great finds, as well as thrift stores in fell’s point.
Thanks so much for your feedback. It’s true that many people think of preppies as stuck up and snobby because they wear expensive clothes. What a lot of people don’t realize is that preppies often raid thrift stores or get clothes passed down to them from brothers or sisters. Preppy clothes are expensive at retail, but they last for years, which is why finding them in thrift stores is so great. Hipster is the dominant mode in NYC, too! 🙂 My old neighborhood in Williamsburg, Brooklyn was hipster-central for the city.