15 Investment Picks for When You’re Ready to Buy One of These Things for Life

15 Investment Picks for When You’re Ready to Buy One of These Things for Life
Buy once, cry once.

As a teacher, I’m not earning as much as my high-school buddies who majored in finance. I’m not complaining at all; I just have to keep a close eye on our budget. And because I’m not a guy with an abundance of disposable income, I’ve really come to embrace the cry-once philosophy of acquiring goods: Let me get the best version of the product right now, so I won’t have to replace it in a year. 

Another name for this cry-once paradigm is Buy it For Life (BIFL). When you save up for a BIFL item, you know that you’re actually saving money in the long term. For example, I’ve had the same leather bag for seventeen years. It cost $550 when I first bought it – no small sum. But in seventeen years, guess how many other leather bags I’ve bought: zero. And that means less leather in landfills, no money I’ve had to spend on a new bag, and less clutter in my closet. I need one bag; I have one bag. 

And if I’m honest, since having kids, I’ve embraced the BIFL philosophy all the more. I love the idea of giving one of my daughter’s my cast iron skillet when she gets her first apartment. I know I’ll be able to do this because Lodge has a lifetime warranty on their skillets and literally says on their website they want me to pass my cookware down to the next generation. Damn – that’ll bring a tear to your eye because when you see a company embrace the BIFL mentality, you buy with confidence and a sense of intentionality. 

This list is by no means exhaustive, but here are a few BIFL items that we’ve come to appreciate at Primer. Let us know in the comments which BIFL items make your cut.


black allen edmonds cap toe shoes

Allen Edmonds Park Avenue Cap Toe $395

Worn by a handful of US Presidents on the day of their inauguration, the Park Avenue is the epitome of American sartorial timelessness. Crafted with a Goodyear welt, it’s built for durability and is easily recrafted by the folks at Allen Edmonds in Wisconsin. 

alden penny loafer

Alden Leisure Handsewn Penny Loafers $663

While the Alden price tag is not for the faint of heart, I can testify to their longevity. I’ve had my Alden loafers for ten years now, and after three resoles, they still look good as new. Alden was founded in 1884 in Massachusetts by Charles H. Alden, who made one pair of shoes a day, painstakingly punching each stitch through the leather by hand. Fast forward to 2023 and Aldens are still handmade in Massachusetts (but at least now they have sewing machines).  


brown oakstreet boots

Oak Street Bootmakers Trench Boot Color 8 Chromexcel $488

Two years ago I interviewed the Vp of Marketing for Oak Street Bootmakers, and I was impressed with his message about the brand: We produce 100% American-Made footwear. Their trench boot got it all started, crafted with Horween Chromexcel leather (which offers great water resistance), and a Danite rubber sole for grip and shock absorption.

man wearing brown whites boots

White’s MP-M1 $680.00

White’s was founded in 1853 and is now known as the leader in boots for loggers (think boots built to take one hell of a beating). Their original Smokejumper boot is what put them on the footwear map, but it’s not what we’d call a “walkin’ around” kind of boot. The MP-M1 pays homage to the military field boot, with a weather-resistant leather upper and a Danite sole. The US-made, hand sewn construction means they’ll probably outlast you, and the clean aesthetic means they’ll match just about everything you own.

Leather Jackets

brown schott leather motorcycle jacket

Schott Chrome Excel Steerhide M/C jacket with full removable belt $1450

Back in 1913, two brothers started Schott NYC by selling raincoats door-to-door. They made the raincoats in their basement and shortly after started making leather jackets as well. In 1928 the leather jackets cost $5.50. While prices have slightly increased, the jackets are still handmade in New York (And the company is still family owned). This one is made with Horween leather and has a full wool lining for comfort and warmth.

man wearing black nubuck bomber jacket while sitting on a fence post in winter

Golden Bear Leather Bomber $1,280

Golden Bear has been making leather jackets in San Francisco since 1922. The premium oily nubuck bomber features a modern fit with a chambray lining and removable sherpa collar for that classic aesthetic.

All-Season Jacket

man wearing a barbour coat

Barbour Classic Beaufort Wax Jacket $425

Barbour is the quintessential marriage of form and function. The Beaufort jacket is made from Sylkoil fabric, which is less stiff than waxed cotton (it’s still waxed, but with a different method). It’s weatherproof and offers a relaxed fit with snaps on the collar for an optional hood and an interior zipper for an extra lining. These guys thought of everything.

man wearing green jacket

Arc’Teryx Atom Heavyweight Jacket $300

With Coreloft insulation, the Atom jacket is perfect as a standalone layer on a crisp fall day or a midlayer for under a heavier coat. It’s packable with moisture-resistance and ventilation slits under the armpits for increased breathability.


rolex submariner

Rolex Submariner Date $10,250

When you think of a Rolex, you think of the Submariner. With its ceramic, rotatable bevel, the Submariner was specifically designed with divers in mind. But you don’t have to be a diver to sport its iconic look. Because this watch pairs well with just about anything but a tuxedo, it’s probably the most versatile watch you can buy.

omega speedmaster

Omega Speedmaster Moonwatch $7600

Chronographs are designed to serve as an ordinary watch as well as a stopwatch. What sets Omega apart is that they’ve been worn during each of the moon landings. This Speedmaster Moonwatch has sapphire crystal glass on the front and back (so you can’t break or scratch it), and a 42mm case.

Leather Bag

brown ghurka messenger bag

Ghurka Harlow IV $895

When I dream, I dream of Ghurka bags. The Harlow IV accommodates a 14-inch laptop and is made with a cotton twill lining to keep weight at a minimum. Made in America with solid brass hardware, it doesn’t get more aesthetically pleasing than this. When my leather bag finally dies (in another ten years or so maybe), I’ll get one of these.


a green briggs and riley spinner suit case

Briggs & Riley Essential 22″ Carry-On Expandable Spinner $699

This may be the most well-thought out suitcase ever made. The handle is attached to the outside, so your clothing can actually lay flat inside. The compartments allow for garment bag like packing, which reduces wrinkles, and Briggs & Riley’s compression and expansion technology allows you to pack the clothes and then compress the entire suitcase like a spacebag. It’s brilliant. Best of all – Briggs & Riley offers a lifetime guarantee with no proof of purchase necessary. So if your bag breaks – they’ll repair it for free, and no, they won’t ask to see your receipt.


tortoise maui jim sunglasses

Maui Jim Kawika $319

I got a pair of Maui Jim sunglasses when I was seventeen, and I still have them twenty years later. The designs are classic; the polarized lenses are of the highest quality, and if you wear prescription lenses, they got you covered.

Kitchen Knife

Wüsthof Classic Ikon 8” Chef’s Knife $200

The best European blades come from Solingen, Germany, which is where Wüsthof has been making its blades since 1814. This 8-inch classic chef’s knife is the perfect all-arounder for the at-home gourmet. Slicing up meat, fish, fruits, veggies, and herbs has never been easier.

victorinox chef knife

Victorinox Swiss Classic Chef’s Knife 8-inch $61

For something a little lighter in hand (and lighter on your wallet), try the Victorinox Swiss Classic. This Swiss-made blade has an ergonomic handle and an extra wide blade.

Skillet and Dutch Oven

lodg cast iron skillet on blue background

Lodge Cast Iron Skillet 10.25” $23.95

I’ve had my 10-inch cast iron skillet for about ten years now, and it only gets better with age. Eggs, bacon, grilled cheese, fish, burgers, whole roasted chicken – you name it, and I’ve cooked it in my cast iron skillet. I’ll be passing this one down to one of my daughters for sure. And you can’t beat the price.

red lodge dutch oven

Lodge Enameled Cast Iron Dutch Oven $299

One thing I really can’t cook in my skillet: Soup. Lodge has recently started making enameled dutch ovens in their Tennessee plant, and they’re gorgeous. Perfect for soups or those slow cooked short ribs.


eastwing hammer

Estwing 16-oz Straight Rip Claw Hammer $41.25

When I bought my first house, my dad took me to the hardware store to get my first set of essential tools. I can’t wait to do the same with my girls, and each of them will get an Estwing hammer. Made with American steel, this 16-oz comes with a hand-sanded leather grip (it’s made from stacked leather rings), which will not only absorb shock but also conform to the user’s hand over time.

leatherman tool unfolded

Leatherman Surge 21-in-One Heavy Duty Multitool $149.95

Yes, this one multi-tool actually has twenty-one tools on it. Leatherman (named after the company’s founder) makes their tools in Portland Oregon, and their twenty-five year warranty means the tools are made to be used hard.


safety razor parts separated

Muhle Traditional Double EdgedSafety Razor $46

I’ve had this razor for about twelve years, and it took me eight years to go through a hundred pack of blades (I only shave like twice a week). So from an economical standpoint, this is pretty hard to beat. The double edge razor gives an incredibly smooth shave and makes it quite difficult to cut yourself. Don’t be fooled by the commercials: you don’t need five blades for a close shave.

Mike Henson

Mike Henson is a literature teacher in Hershey, Pennsylvania. He enjoys shooting 35mm film, restoring vintage straight blades, purchasing too many American-made goods, and spending time with his wife and their three daughters.