Picking the correct piece of footwear can bring an outfit together.
Get it just right and nods of approval will come your way – slightly wrong and it can throw off an otherwise perfect outfit.
Here, I’ve provided a styling guide for a particularly versatile shoe, the American classic Red Wing Boot.
A long-time staple in American workwear culture, they work in a surprisingly diverse array of contexts, from workwear itself all the way to the smart side of casual.
Versatility
Gents, if any footwear brand has stood the test of time, it’s Red Wing.
Founded in 1905, they’ve served American heroes for over 100 years.
From the Pershing 1088, a favourite of soldiers in the trenches in WW1, to the Red Wing #708, a farmhand favourite from the 1950s onward, there’s a Red Wing for nearly every purpose.
From the 60s onwards, they increasingly entered the world of fashion, with models that catered to most social events.
While Red Wing boots are versatile, you need to pick the right one for your outfit.
Not every model is suited to every style of clothing, and it’s important to be conscious of that as a fashionable gentleman.
High Quality
Red Wing boots have long been symbolic of quality.
That same high level of attention to making workwear that lasts means those wearing Red Wing boots in a more fashionable way get boots that look great, and will look great for a long time to come.
The leather they’re made from goes through a complex 30 step process, being tanned, stretched and rolled.
When ready, the upper is fitted with a high-quality rubber sole, a staple of the Red Wing boot, printed with their Logo and grippy in a wide variety of environments.
Classic 6-Inch Red Wing Moc-Toe
A long time classic in the Red Wing line-up, the classic moc toe has become increasingly popular in recent years.
A result of the box-like construction is that it fits a wide variety of foot shapes surprisingly well. Those who have a wide forefoot or high instep may find them surprisingly comfortable.
They’re a popular shoe that goes with a wide variety of styles. More on the causal side of the spectrum, they pair well with jeans and a high-quality wool sweater.
Iron Ranger 8111
The boot was first designed for miners in the Minnesota Iron Range in the 1930s.
The cork in the midsole and the leather insole slowly fit to the wearer’s foot shape, leading to a naturally custom-fitted boot as it wears in.
A staple for both casual and smart casual wear, they match well with jeans and a heavy plait shirt, showing that the man wearing them is tough while comfortable, and ready to spend time on their feet in surprising comfort.
Merchant 6-In
The merchant 6-In is a great Red Wing option if you’re a man looking for a slightly unique approach to business casual.
Try pairing them with a chino pant, ideally made from a slightly thicker, more rugged fabric, and a button-down. For a more in-depth guide on choosing the right pant, check out my trouser style guide.
Adaptable and comfortable, this look will suit a wide variety of more casual work situations.
Sheldon 6-In
The Sheldon is an ideal option from Red Wing boots for gentlemen who enjoy a classic sports jacket.
Slightly more subtle and stylized than some of Red Wing’s other options, they bring business casual closer to the business side, and wouldn’t look entirely out of place in a country club.
The sports jacket allows for a certain sense of maturity. It shows a more serious gentleman in a specific social setting, aware of his surroundings and dressed accordingly.
To find out more about the subtleties of choosing a sports jacket, have a look at my article on the subject.
Williston Oxford
The Williston Oxford is formal enough to be worn with a two-piece suit while retaining a certain independent style.
Let me say this now – the Williston isn’t a true dress shoe, but if you’re willing to take a slightly adventurous approach to smart fashion, it could be perfect for you.
This Oxford by Red Wing can also be worn with jeans or chinos, making it another highly versatile option, potentially one of the best boots for men.
Red Wing Laces
Red Wing boots tend to come with both leather laces and a more traditional braided option.
Subtle style changes such as laces are a great way to add small, personalized touches to your aesthetic, showing that you’re a man with an attention to detail.
If you’re happy with the stock laces – great, they’ll serve you well, for decades if cared for. If you want laces in a slightly different color or material, you’ll be able to find them in any good shoe shop.
Make sure that the laces you buy fit the eyelets in the Red Wings you have.
Most Red Wings have thin laces, and wouldn’t fit wider, flat laces, even if you decided the style was appropriate for your circumstances.
Re-soling
An important care and styling note is that you should make sure you get these shoes re-soled in good time.
Having shoes with worn-down soles is never a good look. It displays a lack of care, a certain contentedness with having possessions that are no longer in their prime.
Aside from the styling notes, if you leave it too long before getting your Red Wings resoled, it may no longer be possible.
Once the leather starts to wear through, shoes can no longer be fixed with new soles, and it might be necessary to buy new boots.
Red Wing themselves offer a shoe resoling service, available in most of their stores.
Leather Care
As with any leather product, it needs to be cared for if you want it to last, and want to look great while wearing them.
Each different type of leather requires a slightly different care approach, necessitating different brushes, oils, and cloths.
To read more on the subject, have a look at my guide on cleaning, conditioning, and polishing leather.
In Conclusion
So, gents, as you can see, there’s a Red Wing boot for nearly every look.
From casual all the way to two-piece suits, what was once a work boot manufacturer now makes an option for almost all scenarios.
If you look after your Red Wings, they’ll last you for years, giving you a high-quality and comfortable set of footwear you’ll likely come to love.
For more advice on choosing the right shoe for your outfit, take a look at my article on the first 5 shoes I’d buy if I rebuilt my wardrobe.
