Red Wing Boots and Chinos For the Stylish Gentleman

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red wing boots and chinos

Red Wing boots are essential for any stylish gentleman. Not only are they comfortable to wear, but they also look fantastic – making them great choices for everyday use.

This iconic brand has seen its following grow over the years and recently ventured into women's footwear. They've even become a go-to choice among celebrities like Ryan Gosling and David Beckham.

The Basics

Red wing boots are a sought-after footwear choice due to their tough and hardwearing quality. While they look great with any outfit, maintaining and caring for these footwear items will keep them looking like new.

These shoes feature one of the oldest methods for bottoming shoes – welt attachment or direct attach, where the lasts are moulded directly onto the boot. This makes them much more flexible and comfortable over time as they break in, though it may feel stiff initially.

To break them in, you'll need to wear them for longer periods of time over several weeks. This process may differ for everyone and take some getting used to, but the effort will be worth it in the end.

Red Wing offers a selection of leather goods to complement their boots, such as gloves and accessories. Crafted from the same tanned deerskin as their boots, these gloves will wear in just as well over time.

The Modern Man

One of the top items on modern men's wish lists is a pair of Red Wing boots. This Minnesota-based shoemaker is renowned for their premium Goodyear welted work boots, but they also specialize in producing shoes that appeal to today's man.

To maximize the comfort and performance of your boots, it is recommended that you break them in gradually over several weeks. This will make the leather supple and the boots feel more comfortable to wear.

To achieve optimal results, wear them inside for 30 minutes per day over several days. You may find it helpful if you use thick socks as well.

For an eye-catching outfit, pair your Red Wings with tailored chinos in dark brown or black. Not only will this combination turn heads, but it's also very stylish too.

The Hipster

One of the earliest hipster trends to hit town was an obsession with 100-year-old outdoor brands like Filson and Red Wing Shoes. These companies, known for their waxed canvas jackets, wool flannel pants, oiled leather boots and other garments worn by hunters, miners and oil rig workers in years past, became popular with fashion-conscious twenty-something burnouts who weren't actually working outdoors but were inspired by it nonetheless.

In 2007, the brand's heritage collection debuted and offered classic styles tailored for American working men. Highlighting this is the Classic 6-Inch Moc-Toe boot, a tough boot ideal for any job and pairing well with selvedge denim or twill chinos.

When selecting Red Wings to wear to work, it's essential that you select the appropriate size. They should fit securely but not too snugly. Furthermore, take some time to break them in properly over at least one or two weeks; this will soften any sharp edges and minimize heel blister risks.

The Stylish Gentleman

No matter if they're wearing a tailored suit or body-hugging sweater and chinos, the fashionable gentleman always looks put-together. These men may appear on magazine covers but what makes them look so put together isn't just natural ability or money – it's paying attention to the small details.

Red Wing boots and chinos make for a fashionable outfit, especially when paired with suits. For warmer months, try dark brown leather Iron Ranger boots paired with light gray suits, or opt for black Red Wing chukkas paired with black suits during the colder months.

It's essential to break in your Red Wing boots properly. We recommend wearing them indoors for about 30 minutes each day over several days to make sure they fit securely.

Thick socks can also help with this process as they add another layer between you and the boots, providing extra cushioning until the leather softens. While it takes some time to break in Red Wing boots, don't rush it as this could result in heel blisters or ankle pain.

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