The Obtainer - 4/29/24, Monday

The Obtainer

April 29th Edition

Presented by

Presented by

Cory Ohlendorf

It’s been a minute since I’ve worn a pair of boat shoes … but I think it’s time. Do I wish I’d saved a few of my old pairs? No comment.

- Cory Ohlendorf, Editor in Chief ⋯ @coryohlendorf


The New Essentials

A Wave of New Boat Shoes

The humble boat shoe has been around for a long time. Sperry Top-Sider originated the style with their signature Top-Sider shoe in 1935 and in the decades since, the Massachusetts-based brand has manufactured them for everyone from the U.S. Navy to preppy and sporting gents of all ages. But just because the iconic design hasn't needed much improvement for the past eight decades doesn't mean it couldn't benefit from a reboot.

After all, in an era of menswear when the “old money” aesthetic is being rediscovered by young people and all things “Dad” are being reworked in modern ways, it was only a matter of time before the quintessential prep slip-on was reworked. In 2024, the silhouette has taken on a more rugged air—gone are the candy colors and white soles, replaced with rough-out leathers and suedes, while some are grounded with thick lug soles. The end result is a little tougher and less blue-blooded. But the revival was inevitable. “Every few years there's another wave,” Lisa Birnbach, the author of The Official Preppy Handbook, recently told the New York Times.

Beefed up and ready for adventure, these new boat shoes pair well with fatigue pants and relaxed, washed denim but, of course, still look at home with your favorite chinos and summer suits. And despite all the changes, what remains is what always drew men to the shoe—an easygoing attitude and sturdy, non-slip soles. Here are a handful that are ready for days on the water or simply strutting down the street.

Our Picks

*** Products - Span ***

The Blackstock and Weber founder puts his spin on the classic boat shoe, cut from a mix of premium leather and suede.

Authentic Original boat shoe,
$375 by Sperry by Chris Echevarria

*** Products - Span ***

Timberland introduced this style decades ago, but the rugged boot lug outsole still feels fresh.

3-Eye lug boat shoe,
$150 by Timberland

*** Products - Span ***

A more streamlined take that feels like the love child of a Belgian loafer and a camp moccasin.

Sconset camp moc,
$198 / $99.99 by Brooks Brothers

*** Products - Span ***

Made in Maine from a soft Bokhara suede, they’re finished with a Rancourt ranger-moc sole.

Ranger moc,
$275 by Todd Snyder x Rancourt

*** Ask The Obtainer ***
Ask The Obtainer

Do you have a nose hair trimmer you’d recommend? What about those waxing kits?

- Cameron

Don't wax it, man. It's painful (really painful) and not only leads to ingrown hairs but also leaves you a little vulnerable. Your nose hair is there first and foremost as a filtration system to catch irritants. You can trim them and they can still fulfill their role as a guardian against dust, dirt and other allergens. As for a quality trimmer, you want one that's simple and safe to operate, while remaining powerful enough to get the job done. This one, from Philips Norelco, is a precision kit with multiple attachments (so it trims not only your nose, but your ears and eye brows, too). You used the dual-sided blades to weedwhack inside your nose or the more standard round nose attachment. Eitherway, the battery-powered trimmer trims quickly without clogging or snagging on the hair.

$19.96 by Philips Norelco

Have a style question
you'd like answered?

Ask The Obtainer "

*** Partner ***


Pick Up a Solid Bracelet
877 Workshop Rhombus bangle

Men’s jewelry has never been more popular than it is right now. And as we head into warmer weather, the right bracelet can be a fool-proof way to add some style and intrigue to an otherwise simple outfit of shorts and a T-shirt. 877 Workshop’s hand-forged bangle is crafted from solid 925 Sterling Silver and hand-stamped with a unique rhombus pattern, created with a vintage steel stamp. It feels like a vintage piece because it’s made the old-fashioned way. Meaning it will withstand any adventure you take it on.


Rhombus bangle, $234 by 877 Workshop

*** Yellow Span - Headlines ***
Smart Buys

The sales and discounts our team is currently watching.

*** Yellow Span - Smart Buys ***

It’s hard to find a knit polo like this for less than fifty bucks. But J.Crew’s Factory label currently has this striped one that looks and feels much more expensive than it really is.

$98 / $49
by J.Crew


Crafted from garment-dyed twill with a touch of stretch, Todd Snyder’s five-pocket chino fits and feels like some straight-leg denim, which makes for a casual yet elevated pant.

$148 / $74
by Todd Snyder


Like a great vintage find, this shirt is cut from a soft poplin fabric in a relaxed, oversized-fit silhouette. But unlike a vintage shirt, this one is cropped so that it’s not too long.

$60 / $36 by
Abercrombie & Fitch


Christophe Lemaire’s UNIQLO U collection still boasts one of the best T-shirts on the market. It’s heavy-weight cotton jersey fabric just hangs perfectly. And now, every color is on sale.

$29.90 / $14.90


These cargo pants from Belstaff have a relaxed fit and come with a drawcord waist and ample pockets. Plus, they’re garment dyed for added softness and color.

$259 / $142
by Belstaff


This clear Nalgene is ready for summertime adventures and is made with BPA-free recycled plastic. This isn’t a huge discount, but it is the cheapest price of the year so far.

$16.99 / $12.97
by Nalgene


Want more?
See all 40 sales »

*** Worth a Read - 1 ***
Worth a Read

The best story from around the web.


Suits, blazers and tailored trousers can and should be worn as part of your everyday wardrobe, both as full looks and mixed into your wider casualwear rotation.”


Three Ways to Wear Tailoring, Casually