Red Wing Weekender Chelsea Review: Work Boots That Aren’t Work Boots

Red Wing Heritage is perhaps America’s most iconic boot brand and typically the first high quality boot a guy buys. They were for me — my moc toe boots inspired this entire website!

Those famous moc toes are a good example of the kind of heavy, tough, weatherproof, Goodyear welted work boots that Red Wing is known for. But a lot of people don’t know that Red Wing has a product line of boots that are lighter, more flexible, and meant to feel more like leisure boots than work boots.

That’s why you need to learn why Red Wing’s Weekender Chelseas are unusual before you make the purchase: there’s a lot to love, and a lot that might turn you off.

Red Wing Weekender Chelsea: The Pros and Cons

I started this blog because I like writing lots and lots about boots, but if you’ve got places to be, here’s a quick summary of the Weekender Chelsea.

Pros

• More flexible, shock absorbent, and lightweight than most resoleable boots
• Removable insole lets you adjust the fit a little
• Available in both oily work boot leathers and more stylish ones
• Snug on the instep; no heel slip for guys (like me) with low insteps
• Resoleable and water resistant stitchdown construction
• Well priced for a boot like this that’s made in the USA

Downsides, But Not Dealbreakers

• No leather underfoot: some guys prefer the kind of comfort you get with a leather insole or midsole
• No shank: without it, some guys get sore feet in boots like this, especially with softer soles
• Not very versatile: most Chelseas are smart casual, but these are firmly casual
• A little hard to get resoled: Unlike most Red Wing boots, these are made with stitchdown construction. It can be resoled, but it’s harder to find a cobbler to do it.

Red Wing Weekender Chelsea First Glance

• More casual than most Chelseas
• Lower profile than most Red Wing boots
• Lightweight and flexible
• Thin sole without much material between the foot and the ground
• Practically no heel

Chelseas have a totally different history to other boots. While America (and Red Wing themselves) has a long history of moc toe boots, logger boots, and service boots, the Chelsea was never a work boot: it was invented as a walking shoe for Queen Victoria.

To this day, many all-American brands don’t sell a Chelsea, finding it hard to square its casual (‘casual’ meaning ‘not for work’) history with the kinds of boots their operations are designed to produce.

But Red Wing has two Chelseas to cover all their bases: the Classic Chelsea is chunky, and Goodyear welted. The Weekender Chelsea is what they call a leisure boot.

That’s an only-slightly-self-conscious way of calling it a shoe.

Make no mistake: the Weekender Chelsea will last years and years longer than a sneaker, but it’s made with a focus on comfort rather than durability: they weigh next to nothing, the insole is soft and foamy, and the sole is pretty thin.

although it’s still got the kind of water resistant build and durable leather that will last you for years, it’s easy to slip on and forget that you’re wearing it.

Men can be a little funny about buying boots that don’t scream “rugged” the way jobsite boots do. (“I’m a man, I only wear tough things!”)

But a lot of guys aren’t always in the mood for the stiff and heavy feeling of Goodyear welted boots, especially if they’re just looking for cool footwear to slip on before walking the dog or seeing some friends.

That’s the Weekender Chelsea: although it’s still got the kind of water resistant build and durable leather that will last you for years, it’s easy to slip on and forget that you’re wearing it.

Red Wing Weekender Chelsea vs Classic Chelsea

Red Wing sells two Chelsea boots right now. Here are the differences!

• Aesthetic: The Classic Chelsea is unusually chunky for a Chelsea, the Weekender has a low profile.
• Construction: The Classic Chelsea is Goodyear welted, the Weekender is made with stitchdown construction. Both water resistant and resoleable.
• Comfort: The Weekender is much lighter, more flexible, and softer underfoot than the Classic Chelsea, which is built more like a work boot.
• Price: The Classic Chelsea is ten bucks more expensive, which is a pretty small difference considering how much more complicated it is.
• Durability: They’re about as longlasting as each other, but the Classic Chelsea’s Goodyear welt construction is easier to get resoled.

Basically: if you love boots because of the way the leather and cork beneath your feet slowly mold to your foot’s shape, you’ll prefer the Classic Chelsea. If you prefer footwear that’s light, soft, and flexible, you’ll prefer the Weekender.

Red Wing Weekender Chelsea Leather

• Copper Rough & Tough leather is the go-to
• Usually available in one or two less work-boot-looking leathers
• Copper is very oily and outdoorsy, with a lot of cool color variation

The Weekender Chelsea seems less popular than Red Wing’s Weekender Chukka, since that one is available in more leathers.

The Chelsea is usually only sold in two or three leathers, but you usually get the choice of Copper (one of their famous work boot leathers) or something a bit less work-focused, like this roughout that my pal Peter wore in a recent photo shoot:

The important thing to note is that if you’re getting the Copper leather, it will develop a great patina: made for work boots, this leather is stuffed with oils and waxes to improve water resistance and reduce how often it needs conditioning.

The cool thing about super oily and waxy leather is the pull up effect: as those components move around the leather with wear, you develop cool highs and lows in the color.

Red Wing Weekender Chelsea Construction

• Polyurethane outsole
• Texon midsole
• Removable, leather topped foam insole
• No shank
• Stitchdown construction

The main thing to note is that these are lighter and more flexible and more shock absorbent than the better known Red Wing Heritage boots. Those kinds of boots are great and they’re comfortable, but in a different way that largely revolves around stability: the other Red Wing boots have a stiff leather insole with cork underneath it that slowly molds to the shape of your foot with time, ultimately producing a boot that’s molded to the shape of your exact foot. It’s neat!

These boots also have steel shanks, which refers to a stiff piece of material placed inside the boot’s construction between the heel and the forefoot. A shank helps keep your heel and forefoot from moving independently of each other throughout the day, and this a big reason why many folks find boots more comfortable to wear all day than sneakers.

You don’t get any of that here: no shank or stiff leather insole. These boots focus on a different kind of comfort: softness!

So the layers underfoot are a removable, leather-topped foam insole; a Texon midsole (that’s a kind of cellulose), and a polyurethane outsole that functions a lot like traditional crepe rubber, but it’s harder wearing. In addition to being made of spongier materials, there’s also simply less material between your foot and the ground — check out how thin the sole gets at the forefoot in the picture above this paragraph.

So the main question you need to ask yourself is if you like the idea of a lighter and more sneaker-feeling boot, or if you prefer the hard and sturdy feeling of more traditionally made work boots. There’s no right answer, but I love having this option and I love that Red Wing decided to produce this line of “leisure boots.”

Stitchdown vs Goodyear Welt

One last note about the build: most boots are made with Goodyear welt construction, these are made with stitchdown construction. Many guys think stitchdown makes a tougher boot that’s harder to make, largely because it’s the preferred construction method of Pacific Northwest boots.

Stitchdown can be used to make super tough boots, but it can also be used to produce boots like these that are simpler and more flexible.

All you really need to know is this: opting for stitchdown let Red Wing make these boots more flexible than their other boots and it’s still resoleable, but you might have a harder time finding a cobbler to resole them.

Absolutely any cobbler will resole a Goodyear welt, but phone ahead if you’re trying to resole one like your Weekender Chelsea — if you aren’t surrounded by cobblers like we are in New York City, you may need to mail your boots to someone when it’s time to resole them.

But it can be done! Check out these Weekender Chelseas from my pal Rob; if you look closely, you can see that’s not the original sole.

Red Wing Weekender Chelsea Sizing and Fit

• Order your true size
• I’m 11 in most Red Wing boots and 12 in most sneakers; I’m meant to get 11.5 in these.
• But you should size down 0.5 if you have a low volume instep like me

My true size is 11.5, I got these in an 11, and while they were a bit tight on my pinky toes at first, they quickly softened up. That was before I learned I was meant to order my “true size” of 11.5.

Before ordering these boots, find out your Brannock size: that’s the number you get when you measure your foot on that device in a shoe store. (And it’s usually 0.5 smaller than your sneaker size.) Ideally, ask the clerk if you have a high or low volume instep.

If you have a normal or high volume foot, you’ll be fine with your Brannock size, a.k.a. your true size. Me, I have a low instep, which makes Chelseas hard to fit: if your instep doesn’t fit right, your heel slips. So I wound up sizing down 0.5 to an 11, and they fit me great — there was no heel slip and I’m still nowhere near the end of the boot.

Red Wing Weekender Chelsea Price: Are They Worth It?

• $279.99
• It’s a good price for an American-made resoleable boot

Almost every Red Wing Heritage boot costs over $300, but they made sure the simpler construction was reflected in the price: these are currently $280 at Red Wing Heritage’s store and at Huckberry, who I find have better customer service.

That might sound expensive and I won’t pretend it’s not a lot of money, but I encourage you to click around this list of USA-made boots — you’ll quickly realize that it’s very unusual to find an American-made resoleable boot for under $300.

In summary: I like these boots and I like that Red Wing put this much effort into making boots that are still durable but more comfortable for the average person.

These boots aren’t for you if you need a shank, if you prefer leather underfoot, if you need any ASTM ratings, or if you’re looking for smart casual Chelseas that aren’t hard to dress up.

But they’re a great choice if you want a longlasting boot that’s lightweight and easy to slip on.