Vintage pens
I define a vintage pen as any 20th century (or before) pen model that is no longer in production.
Tangent: Acquiring old pens
I generally don't advise going out of your way to get a vintage pen as your first one. They're typically more expensive than equivalent modern pens, and you don't have a ton of recourse if something goes wrong. It's also harder to tell if you're getting fleeced if you don't know that much about fountain pens in general. But if you get an old pen as a gift or inheritance, absolutely use it! My first fountain pen was my mom's old one.
The best place to buy vintage pens is at a pen show because most pens will be repaired and ready to write, and you can look at pens before you buy them. Online sales are riskier, but there are some reputable dealers out there like Peyton Street Pens. Estate sales, thrift stores, and antique shops will have the most variable results, especially for older pens with in-built filling systems. In general, you should go in expecting something to be wrong with the pen, and if that ends up not being the case, you'll be pleasantly surprised!
Lever fillers
Lever filled pens are built with a latex ink sac attached to the nib section. A lever in the barrel operates a pressure bar inside the pen, which squeezes the ink sac to take in or expel ink. You can read more about lever filler anatomy at Richard's Pens (an excellent resource for vintage pens).
Esterbrook J (1948)
Esterbrook is an American pen company that started producing fountain pens in 1920. It closed its doors in 1970 but was revived under new ownership in 2018. The Esterbrook J was first introduced in 1943 and went through a few different iterations until the "Double Jewel" model was released in 1948. It's hard to date Esterbrooks released in 1948 and later, but it's still possible to narrow it down if you pay attention to small design tweaks. This pen was definitely made in 1948 because the embossing on the barrel says "Esterbrook" and not "Esterbrook ®;" the change happened very early on in the production timeline (see Esterbrook.net)
The J was designed to be affordable but durable, so the pen is made out of unusually high-quality materials for the time (celluloid and stainless steel). Esterbrook produced a wide variety of nibs to swap in and out of the J, and this system was successful enough that other pen companies like Osmiroid released nibs that are inchangeable with Esterbrooks.
I got the Esterbrook J at the 2024 Colorado Pen Show. The seller quoted me $20 for it. Before giving it to me, he looked at the nib and told me that the nib itself was worth at least $20, but he'd honor the original quote. The nib in question was a 9048; I learned afterwards that 9000 series nibs are of the premium "master series" variety, and this particular one is a "Flexible Fine". It's not a super soft flex nib and the tip is kind of scratchy on some paper types, but I still like it for drawing.
The J is small and lightweight, so it's a nice travel pen. It also feels durable enough that I don't feel too worried about it being jostled around in my bag.
Osmiroid 65 Mark I (1954-1960)
Osmiroid was an English pen manufacturer that started producing fountain pens in 1948, later going out of business in 1991. The Osmiroid 65 was one of Osmiroid's first models. It was produced from 1954-1960 and primarily marketed towards students. This pen is the "Mark I" version of the pen. A newer "Mark II" version was produced starting in 1960. The two models can be differentiated by the top of the cap; on the Mk I, the top is slanted, and on the Mk II, the top is flat). Osmiroid produced a massive range of nibs for different writing styles, but their italic nibs appear to have been the most prominent in their marketing.
I got the Osmiroid 65 in a box set with 5 different italic nibs for $7 at a secondhand art supply store in 2024. I was expecting a project because I figured the ink sac was completely degraded from age and use. I soaked the pen for 2 days just to unscrew the nib, then used an embossing gun to separate the pen body from the grip section because it wasn't designed to be removed. It turns out the ink sac was completely intact and just needed to be cleaned, a very pleasant surprise!
I don't care much for the pen itself because the body is cheap plastic and the cap doesn't seal that well, so the nib dries out after a few days. But the nibs are beautiful crisp italic nibs that are worth much more than the $7 I paid for them. My hope is to eventually get another Esterbrook J to put them in.
Cartridge/Converter fillers
Cartridge pens have been in development for a very long time, but they achieved prominence in the 1950s and are now the most common filling system you'll see. These pens take plastic ink cartridges in addition to converters, which allow you to fill the pen with bottled ink. (You can also just use a syringe to refill cartridges, but anyway...) Once again, Richard's Pens has a nice history of pen cartridges.
Vintage C/C pens are "safer" than lever fillers because you don't have to worry about the ink sac disintegrating from age or poor reactions with certain inks. I also personally prefer the designs of a lot of 1970s-1990s pens.
Waterman Gentleman (1970s-1980s)
The Waterman Gentleman was a high-end Waterman pen that was first produced in the mid-1970s. It marked the beginning of the slim cylindrical Waterman period. The body is lacquered brass with an 18k gold nib. It's pretty heavy and expensive-feeling, but not in an unwieldy way. I bought this pen at the 2024 Colorado Pen Show from an English man with a sizeable collection of 70s-90s pens. He sold it to me for $150, which is a bargain given the 18k nib!
The nib is broad and looks slightly oblique, but it's hard to tell if that was intentional or if it was worn down from use. The nib is very soft and has some flex/bounce, although it's not a true flex nib. After I started using it, I noticed the pen was suffering from a lot of hard starts, so I took it back to the pen show the next year to have Kirk Speer work on it. It works great now and spews a lot of ink.
Waterman Laureat I (1985-1990)
Waterman is an American pen company that was formally established in 1888, although its owner L.E. Waterman had patented his first fountain pen design in 1883. A French subsidiary of Waterman was established in 1914 and was operated mostly independently from the original American company. In 1954, the American Waterman closed and was acquired by the French Waterman. Waterman is still around and has been acquired by an American parent company, but the company headquarters and manufacturing are still in France. Most modern Watermans just aren't as good as the old ones.
The Waterman Laureat was a mid-range pen first produced in 1985. The body is made of lacquered brass with some plastic on the section and finial, and the nib is gold-plated steel. The design is the slim cylinder type that was popular at the time, and the lacquer came in a variety of different colors and patterns. This pen is now known as the "Laureat I," the first version of the Laureat that was produced until around 1990; afterwards, the second edition was produced until it was discontinued in 2000. The Laureat I looks slightly plainer than the II.
This pen was my mom's, so it was sitting in a drawer for an excessive amount of time until I found it in 2023. It took days of soaking and rinsing to get all the dried ink out. My mom used this pen frequently, and you can tell it's been well-loved from the absolute state of the nib. Despite all the wear, this is far and away the nicest steel nib I've ever used. It's very stiff and flows a bit dry, which causes it to produce some subtle texture and line variation that you don't really get from steel nibs anymore. It makes my writing look very fancy. The pen itself feels fancy too, with how hefty the brass is.
Sheaffer Fashion II (1990s)
Sheaffer is an American pen company that was founded in 1912. It was a very prominent name in the American fountain pen landscape for nearly the entire 20th century, but it fell out of style and eventually closed its original American factory in 2008. Sheaffer has been passed around between owners a few times and still makes pens, but it's greatly diminished from where it was at its peak.
I can't find a lot of information on the Sheaffer Fashion line. It debuted in the late 80s or early 90s with the Fashion I, an ultra-slim pen that came in a variety of mostly pastel colors and was primarily marketed towards women. Pens!! For women!!!! The Fashion II line came later; these pens were larger and came in bolder colors and patterns. The Fashion I pens are so small that they require Sheaffer slim cartridges and converters (pretty hard to find), while the Fashion II pens take standard Sheaffer cartridges. The body is lacquered metal, and the nib is gold-plated steel.
My pen was purchased new old stock in 2024 from Peyton Street Pens, meaning it's unsold inventory rather than a true secondhand pen. It was $50. The nib is nothing special, but it works as well as you'd expect it to. It's very smooth to the point that it's almost hard to control on super smooth paper, but it looks and feels great on textured paper. I might take it in for a nib grind to correct this at some point.