Finding the right combination of words from the vintage lexicon to track down what you’re looking for in the world of Search Engine Optimized online listings is equal parts science and art — but, the kinds of science and art that make you sort of sad, because you can’t believe someone spent so much time learning how to turn recycled sheet metal into a flamingo, or that someone else ran enough experiments to find out how scared dogs can get about fireworks.

I’ve spent enough late nights and slow workday afternoons deep diving the far reaches of the e-commerce landscape and reverse image searching hyper-specific garments to be well-versed in the pitfalls and triumphs of this somewhat sad science. I’ve also written a lot about various hidden gems in the past, in hopes of putting this otherwise futile, mental trapper keeper full of information to good use.

While I love finding a rare or unique piece of clothing, there’s a tremendous amount of satisfaction in bringing home something that feels at harmony with 2024 styles for a fraction of high-end prices (while also avoiding fast fashion shops). I’ve wanted to share a few brands and specific finds that consistently nail that delicious vin diagram of design, quality, and price in a way that’s almost impossible to find outside of secondhand shopping.

In future posts I’ll run through sweaters, outerwear, sportswear, hats, and pants, but today we’re starting up top, with shirting. (FWIW – While the shirts mentioned are technically menswear, they can absolutely be worn as unisex!)

The world of vintage shirting is it’s own rabbit hole within the sprawling catacombs of vintage fashion. You can find tons of brands across various time frames making excellent clothes that sell for affordable prices, which many people across the internet have their own opinions on.

For my money, no one offers the diversity of silhouettes, colors, and textures that Polo Ralph Lauren does. Beyond the unique designs, the standout feature of throwback Polo is their fit. It was perfected in the 90s — slightly wider in the shoulders, roomy in the chest, flowy but not obscenely oversized sleeves, with length to tuck (which can be hemmed for an untucked or cropped look for $10 at your local dry cleaner).

So how do we narrow down the search? The first thought for many is to try certain trendy “fit” features like “Boxy Fit”, “Oversized”, “Cropped”. Or maybe you start with a broader category like denim shirts, flannels, or overshirts. Unfortunately, aiming for broad topics can leave you with thousands of options to sift through, even if you narrow by size! And tapping on trendy search terms will often lead you into the lions den of expert vintage curators who may have good stuff, but they’ll almost certainly be at premium prices (think $50-$80 for standard shirts, $150+ for more unique tops).

So how do you find something more affordable, like the examples above that were each between $15-$50? My first suggestion is to use your search terms instead of filters. While I love the eBay, Etsy, and Depop filter tools for broader, initial searches, not every seller lists their products in great detail. This means you can often overlook things where the seller may have listed a size, color, texture, or even brand in the title or description, but left the details empty (or even filled them out incorrectly).

Your search should generally look something like this: Vintage Polo Ralph Lauren Mens Flannel Shirt Medium Red Plaid Cotton. Obviously you can mix the terms around with whatever color, style, or material you’re looking for, and it should yield good results! You can even throw in terms like “made in USA” to specify the search more and find what are generally considered to be higher quality pieces from the 90s.

If you want to take your deep dive even further, you can start making note of certain silhouette names that pop up often in your results. Barbour, for example, is a heritage brand whose core jackets (Bedale and Beaufort, among others) have been the used for decades now, so examples exist all over the internet. Searching by specific product name gives you a much more narrow pool of options to sift through, and if you already know you like the style and fit of one shirt or pant option, you can have a lot more confidence in your searches going forward.

Here are the three Polo Ralph Lauren shirts I’ve had a lot of luck with over the years, which can work as unisex shirt options, if you can find the right size:

The Benford

The Benford (far left) is a workwear style shirt that is currently my favorite option because of their wide range of interesting fabrics and its excellent fit. It’s a more casual look due to the two button closure, flap pockets on the chest and a relaxed collar. I’ve found the sizing to be fairly true-to-size (for reference, I’m 5’10” and 175lbs and usually wear a Medium, though I do have a size Small that works, too), although I always recommend double-checking the measurements anytime you’re buying vintage.

For the warmer months, you can find the Benford in very drape-y silk-cotton blends (pictured earlier in this post on me in navy blue, which was my favorite shirt for summer), while there’s a smattering of flannels, corduroys (with elbow pads), plaids, and houndstooth patterns that feel quintessentially autumnal.

Prices typically range from $20-$50 (heavier fabrics tend to cost more), but there’s a good number still under $20 as well. I’ve put together an initial eBay search for you here.

The Andrew

Next on the list is one of the most classic offerings from Polo. The Andrew shirt (pictured above in the middle, in a pale blue, cotton herringbone twill fabric) is akin to the iconic, preppy pleated pants and shorts style, which also carry the same moniker from Polo. Either delivered with one chest pocket or no pocket with a Polo Horse emblem, this shirt is slightly more… well, buttoned up, with a stiffer collar and classic fit.

These shirts are broadly made of 100% cotton, with classic plaid patterns, solid colors, and, my favorite option, herringbone twill. I love this shirt for how true the fit is and the sheer amount of design options you can find. It has a slightly more flattering shape than the Benford’s oversized, boxy feel, while maintaining the billowy drape that feels like it belongs in Notting Hill if styled right.

This is the most cost effective option on the list, usually ranging between $10-$25. I’ve purchased all 3 of mine for less than $12 each, so offer low and see what happens! For sizing reference, I am consistently a 15 1/2, and am 5’10”, 175lbs. I have one in 16 1/2, and it fits oversized, in a good way (seen here). Check the measurements, but I would say these are true to size.

Shop the Andrew Shirt here!

The Marlowe

The Marlowe (pictured above, far right, in a navy blue, corduroy-textured, cotton-silk blend) is the platonic ideal middle ground between the Benford and the Andrew. I got this specific one for Anna a few months ago, and the texture and weight of it is insane.

Much like the Benford, the Marlowe can be found in an slew of fabrics and patterns, many of which are really fun and interesting. Similar to the Andrew, this silhouette has a stiffer collar and will either have a single, chest pocket or a Polo horse emblem. The fit is slightly more oversized than the Andrew, but generally appears to be TTS as well.

The specific texture this shirt has seems to feel a bit heavier than the other two options, and as a result, drapes really nicely. Lastly, there are also a lot of wacky patterns available in this cut, which is fun if you’re looking for something a bit louder.

The Marlowe prices fall in line with the other two, but there are definitely some unique prints and fabrics that push some pieces well above $50 or even $100! Still, you can find a ton of options below $20.

Shop the Marlowe here!

I hope these three options give you a good starting point for bringing home premium pieces at an extremely affordable price!