Everyday Style: The Best Men’s Casual Boots to Wear with Jeans

Everyday Style: The Best Men’s Casual Boots to Wear with Jeans

Jeans and leather boots are durable, modern style essentials. Denim entered American culture in the late 1800s courtesy of a tailor named Jacob Davis and a patent procured by Levi Strauss & Company. The Levi’s patent covered the use of rivets to create fast, durable pocket openings on garments. What began as workwear evolved into the easy, iconic wardrobe staples we know today. Casual, comfortable and classic, there’s nothing more effortlessly cool than a handsome pair of men’s boots with jeans.

Handcrafted premium leather boots evoke laid back sophistication and rugged timelessness. Whether you’re looking for the perfect pair of boots to wear to the office, resolable footwear, or the most comfortable shoes for travel, our premium leather styles fit the bill.

Just like your favorite pair of jeans, HELM boots fit and feel better the more you wear them. Keep reading for the HELM guide to the best men’s casual boots to wear with jeans…everyday.

Moto Boots

Tailored and minimalist, a fine leather moto boot never goes out of style. From heeled, 1960s Beatles boots to Italian zip-up style, moto boots are enduringly fashionable and easy to wear. Part roper, part moto, part Chelsea… HELM’s modern take on a fine leather moto boot, The Pablo, features a casual, rounded toe profile, side zipper, and reinforced pull tab detail. Available in black, brown and teak Balthazar leather, The Pablo is a travel friendly ankle boot that pairs naturally with denim. Keep reading to discover how we’re styling every color of moto boots with jeans…

Black Finished Leather Moto

Black leather reads equal parts elegant and tough. Black moto style boots are among the most versatile men's boots to wear with jeans. They pair equally well with slim jeans in both dark and light wash. Matte black, dark-grey, or dark-blue denim balance the moody sophistication for a professional and artful energy. Black on black always works. 

To style a chelsea boot with a straight leg or slim fit jean, opt for a French cuff or have the hem of your pants tailored to break just above the vamp of the boot. Proper tailoring will prevent the pant leg from pooling at the top of the shoe. Many retail shops offer this service complimentary. Be sure to ask when you purchase your next pair of jeans.

 When investing in fine leather goods it’s important to keep the hide conditioned with a regular polish and buffing. Leather wax, oil, grease, and balm all make caring for your premium leather boots easy.  Protect your investment and you’ll enjoy your HELM for years to come with a boot oil kit.

Brown Finished Leather

Handcrafted brown leather boots are a Mens Fall style must have. The Pablo in supple Rockford Brown pairs with slim-cut or straight leg jeans, cuffed or uncuffed. If you’re looking for a pair of mens casual boots to wear with jeans, brown leather moto boots add warmth and depth to any ensemble. We especially love a brown leather moto boot with all black. Yes, you can wear your brown leather boots with black denim. Either add in some neutral tones from the waste up, balancing the look with a leather jacket or matching belt.

Drawn to the monochromatic trend? Try brown or tan jeans with a crisp white button-down and blue tie for work. Light or neutral jeans paired with a dark-brown, grey or tan hues channel refined luxury and smart casual style. When working with a tone on tone color palette, mix up textures. A thoughtful juxtaposition of knitwear, cotton, suede or velvet in complementary colors evokes multi-dimensional appeal.

Teak Finished Leather

Teak leather possesses a rich bourbon hue with a pronounced pull-up effect. HELM teak leather boots break-in easily and develop character variance with each wear. Blue denim in any colorway pairs beautifully with teak leather. The warm, orange tonality of the hide often matches Levi’s or classic denim stitching. Reach for a vintage tee and jacket to make it a casual outfit.

Dress up your teak leather boots with a pair of blue or navy trousers or wear casually with jeans. 

Add a matching belt to elevate the look for work or a special event. Matching your leather goods, watch, belt and accessories to your boots results in a look that reads cultivated and intentional. 

Desert Boots

These ankle boots go to battle for you in both style and function. Worn by British Eighth Army soldiers on the North African front during the Second World War, the style is regarded the world over for its ease, comfort, and durability. The original crepe rubber soles was designed to flex on varied terrain, while a suede upper stayed lightweight and cool in the desert heat.

HELM desert boots feature a polished, modern update. The Declan is outfitted with a durable, leather and poured rubber Fineline outsole for a look that is at once polished and at ease. The low profile Chukka boot style is a casual, elevated everyday boot capable of being styled a myriad of ways, especially in classic tan suede.

Black Finished Leather

black leather boots with jeans

Black leather desert boots are easy to dress up or down. A classic and casual men’s boot to wear with jeans, black desert boots remain in style for years to come. Ankle boots are a simple way to make jeans and a tee shirt look instantly more professional or cocktail hour ready.

Go high contrast by pairing black boots with a white tee and jeans or neutral tones. When it comes to wear patterns and patina, black leather boots are notoriously the easiest color to touch up and least likely to show pronounced wear. Polish your black chukka boots every few months to keep the uppers healthy and conditioned.

Brown Finished Leather

A brown leather desert boot is casual and understated. We love to recommend brown leather chukka boots for weddings and events, in particular when guests ask for a shoe that won’t need to be broken in. Since the profile features a lower shaft height with less laces, the tongue of HELM Declan boot is more pliable and supple when new. The lower profile also pairs well with straight leg trousers from denim to suits.

Up top, desert boots work well with the same shirts and jackets as their brown finished leather moto boot counterparts. Think crisp-white button downs, blue ties, and brown blazers. Another winning combination for us is pairing raw-denim jeans with a white tee and brown sweater. The juxtaposition of mens boots with jeans is richly textured and well cultivated.

Tan Suede

Looking for a more casual boot with jeans? The Declan Suede is your color, style, and material. Tan suede is a natural match for denim in any number of washes. We often field questions about how easy our suede is to clean. The answer might surprise you. With a simple suede protector spray and regular upkeep with a Tampico brush, HELM tan suede is easy to keep clean. Pliable and soft right out of the box, suede Chukka boots have a zero break-in period. 

Tan suede can be worn monochromatically with khaki and neutral slacks or with jeans of any color. The low profile of The Declan is perfect for showing off your sock collection. As a team, it took us nearly a year to develop the perfect pair of HELM socks. We designed our marled and striped HELM socks with a cushioned sole for extra step-in comfort. We set out to create the best socks to wear with boots. You tell us if we succeeded.

Railroad Heritage and Work Boots

railroad men's casual leather boots

Heritage boots are as All-American as blue jeans. Crafted by hand using only the finest materials, HELM heritage boot styles are made in USA at our family owned and operated Maine facility. The Marion, The Muller and The Railroad boots are all inspired by round toe American heritage work boots. Today, the Americana look is often associated with hipster boot styles. HELM heritage boots are updated with durable, modern details from mini-lug soles to triple stitched toe caps. No two pairs are exactly alike.

Our made in USA styles fit close to the ankle, making them an ideal choice for styling with skinny, wide or straight leg jeans. Wear full and straight or cuffed to show off laces. Try black-denim jeans with a matching denim jacket or layer up for the outdoors with a cable knit sweater or waxed military canvas jacket. Durable and built to last, your HELM boots are designed with care and attention to navigate all roads in style.

Grab A Pair of Men's Casual Boots To Wear With Jeans

From chukkas to Chelseas, shop our full collection of casual boots to wear with jeans here. We handcraft each HELM with premium comfort and longevity in mind. Our designs transition effortlessly from work to street wear, from the boardroom to the bar. Enjoy 10% off your first pair of HELM + free shipping and free returns always.

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