Chelsea boots are smart, stylish, and slick. But here’s the thing: those boots will only look good if you know what to pair with them. So today, let’s break down what to wear with Chelsea boots, along with some great outfit inspiration.
Color Coordinating – Black & Brown Are Perfect
To maximize how good your Chelsea boots look with the rest of your outfit, coordinate them with black and brown shirts, slacks, and jackets. In fact, black and brown are the go-to colors for any outfits involving Chelsea boots for men. Why? Chelsea boots are universally in dark shades like black and brown. So, for example, if you lean into those shades with your other clothing articles, you’ll evoke a put-together, comprehensive, unified aesthetic that no one can miss.
Tailored Slacks and Blazers
But what about specific clothing articles? We recommend putting on some tailored slacks and wearing your Chelsea boots with a blazer (plus a nice shirt, especially with a high collar if you are getting dressed in the winter). Tailored slacks and boots are semi-formal, though not so formal as to be stuffy. As a result, they are perfect for pairing with Chelsea boots for smart-casual social occasions, like parties or receptions. They also go well with most Chelsea boots’ sleek and elegant outlines, making your outfit look mature and modern.
To round out the outfit, consider picking up some stylish and perfectly tailored slacks, like these Super 100s Gabardine pleated trousers from Berle. The proper trousers will tie your Chelsea boots and your blazer/button-down shirt together. As a bonus, they’ll lengthen your silhouette, making you appear taller.
Good Jeans and a Hoodie or Button-Down
That said, you can also wear your Chelsea boots with nice jeans. Then, combine those with a hoodie or a button-down shirt for a slightly more casual aesthetic, which wouldn’t be out of place at a nice dinner date or family holiday celebration.
However, your hoodie should be in relatively good condition and without any graphics or images on the front. Remember, your Chelsea boots aren’t purely casual by definition, so you can’t go too far down the “casual” side of the style ladder.
For jeans, opt for high-quality denim trousers, like these Dress Denim slacks from Berle. Nicer jeans usually go better with Chelsea boots than casual or beat-up ones unless you are trying to cultivate a workman’s look (see more below).
Slacks and a Leather or Smart-Casual Jacket
Consider pairing your Chelsea boots with slacks alongside a leather or smart-casual jacket to take things back up a notch. A leather jacket, for example, will go perfectly with your Chelsea boots since they are usually made from a similar material. In addition, using similar textures in your outfit will automatically create coordination and unity, tying the entire outfit together.
Any smart-casual jacket will also work well with Chelsea boots. Choose a black, navy, or brown coat for the best effect.
Workman’s Jeans and a Sweater or Flannel
What if you want to wear your Chelsea boots but still evoke a blue-collar style? It turns out you can; simply combine them with slightly more distressed or durable jeans than the dress denim slacks mentioned above, plus a sweater or flannel.
The right workman’s jeans will look good with your Chelsea boots, especially if the shoes aren’t brand-new. When choosing your sweater or flannel, consider the above color considerations. Generally, dark-colored sweaters and flannel shirts are better than light-colored options, as they will coordinate with the colors of your boots better than otherwise.
Of course, jeans aren’t the only trousers you can wear with a sweater and your Chelsea boots. Other workman’s trousers, like classic khakis, are also great options. Khakis, like those made by Berle, are durable, available in many different colors and sizes, and perfect for rounding out this blue-collar yet still stylish aesthetic.
Overall, there are plenty of options regarding what to wear with Chelsea boots. To personalize your ensemble, consider your personality and likes, then tailor your outfit collection accordingly.
Get the Look at Berle
Here at Berle, making trousers is nothing new. As the oldest family-owned trouser manufacturer in the United States, we’ve been outfitting our customers for over 70 years. In that time, we feel we’ve perfected the art of making and delivering the best pair of trousers available today.