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Men’s Style Guide: How to Wear Boots to Any Occasion

From casual boots to wear with jeans to dress boots and dress shoes, our guide to boot fashion trends you need to know now…

 A quality pair of handcrafted men’s boots is a luxury good investment that will maintain its comfort, style, and appeal for decades. We’re firm believers that every closet needs a reliable pair of well-made boots. HELM styles are designed to be worn at a number of functions and occasions. We like to say our boots will take you from the boardroom to the bar, and we handmake each pair with the intention of creating timeless looks all walks of life. A good pair of boots will see you through almost anything. Who can say the same of sandals…

Men's Fashion Boots - Tips on Wearing Boots

Maybe it’s the Texan in us, we’re firm believers boots belong at every table and every party. Whether you’re looking for casual boots to wear with jeans, smart casual shoes, dress boots, or the best boots for travel, we’ve got something in the HELM lineup to fit any event or lifestyle. Keep reading to find out how to wear boots for formal and informal settings, how to style men’s boots with suits and jeans, and how to know what pair of HELM is right for you….

1. Wearing Ankle Boots

The fashion industry is known for its mercurial taste and cyclical trends. As passionate bootmakers, the thing we love best about designing HELM boots is the longevity and integrity built into each in every pair. Boots aren’t a trend. Investing in classic boots styles made with high integrity construction and top grade hides is a fashion choice that won’t go out of style. What’s more, investing in handmade goods will ultimately lower your overall cost per wear. Good shoes are good for the environment.

If you’re wondering when to wear boots, our answer is: Always. Styling casual boots and dress boots alike for formal to informal occasions all comes down to achieving the right mix. We’ll offer our tried and true tips for creating the right balance of casual comfort and handsome sophistication. A dependable boot means confidence from the ground up.

How To Style Men's Ankle Boots

Ankle boot style are among the most versatile casual men’s leather boot styles. Low profile boot styles have an advantage when it comes to comfort and tailoring. A shorter shaft often allows an ankle boot design to pair effortlessly with any length or cut of trouser leg. Desert boots play well with everything from jeans, khakis and slacks to sweaters , tees and button-up shirts.

When To Wear Ankle Boots

Chukka boots such as HELM Declan Brown leather boots are a comfortable choice for smart casual and business casual outfits. A chukka boot is streamlined and easy to wear, with a minimal (some would say zero) break-in period. Desert boot styles like the Declan Men’s Black Leather Boots add polish and intentional detail to a laid-back jeans and t-shirt look. The ankle boot style is a perennial classic with roots in military history. Designed for functionality in warmer climates, a low profile desert boot is the perfect choice for Summer and Spring fashion.

Chelsea boots in zip up and slip on profiles offer another ankle boot style option. Traditionally, Chelsea boots feature a lace-less design with zippers, elastic or vulcanized rubber on the side of the boot. The HELM Pablo boot is a mix between a moto boot, Chelsea boot, and roper style cowboy boot. The Pablo’s zip up design makes it ideal for travel and the minimal aesthetic looks effortless and handsome paired with anything from a suit to blue jeans. An elegant pair of black Chelsea boots never goes out of style.

If styling a dress boot or Chelsea boot, such as the Pablo, with a tailored suit, the trick is to be sure the break in your trouser pant leg happens at the right point in the boot’s upper or vamp. If your trouser leg break is too low, the pant leg may pool at the bottom of the boot. Proper tailoring guarantees a precise and well-manicured look.

If you’re going to the office, a nice pair of chinos or sports coat looks refined with a desert boot or leather Chelsea boot. Men’s black leather boots read confident and tough. Balance the look of a casual outfit with restrained neutral tones and refined accessories. The juxtaposition of edgy appeal with edited detail adds dimension for a layered luxurious look.

The Pablo and The Declan are two styles we often recommend to guests packing for a destination wedding. Knowing you can take a single pair of shoes on vacation that ties in beautifully with every outfit in your suitcase saves space, time, and effort. Take the guesswork out of travel and wear a Pablo straight to the airport. You’ll have extra room in your carry-on for souvenirs.

2. Wearing Military and Combat Boots

Military combat boots are quintessential men’s boots known for their rugged and enduring appeal. A high quality, handcrafted leather boot adds tough and practical integrity to casual wear. Combat boots and brogue boots make casual outfits ready for adventures on the road. Built to handle a multitude of terrain, military and combat style boots can often handle the outdoors as well as a hiking boot or waterproof boot.

Combat boots look edgy handsome paired with muted earth tones, black jeans, and trousers. We love the look of tan suede with khaki or army green canvas. HELM cap toe boot styles from the Muller to the Hollis take cues from traditional Americana and military combat boots. Our Ryder and Johnson boots both feature the HELM Stavos sole, inspired by a military paratrooper outsole. Style a pair of black leather boots with dark jeans and a denim jacket to keep the look laidback and easy.

The Hollis in Black Leather is among the most versatile and transitional styles in our lineup. This cap toe boot style features a mini-lug outsole and tapered toe profile. The combination can read as an elevated combat boot when paired with casual attire or a practical dress boot when polished and worn with trousers. In designing the Hollis, we wanted to create a transitional style that could be styled for a number of occasions. Comfortable and tailored for an impeccable fit, this classic men’s style is effortless and built to be worn.

How to Wear Military and Combat Boots

The key differences between a military style boot, combat boot or men’s work boot is often the height of the boot’s shaft and shape of the toe profile. HELM Johnson boots features a high profile with speed hook lacing and military paratrooper sole for a look inspired by a traditional military combat boot. The Ryder with speed hook and D-ring lacing, padded ankle, and Stavos outsole combines the durability and comfort of a hiking boot with a modern work boot aesthetic. Both boots have a generous rounded toe profile for extra comfort and mobility.

Styling military and combat boot is all about the interplay of elements. Military styles can read severe or tactical. The right balance and mix of materials and accessories allow combat style designs to read fashion forward and deliberate. Show off the high profile with a French or rolled cuff to your jeans or pants. Thinner laces are often a quick and easy hack for dressing up casual boots. You’d be amazed what a crisp, fresh pair of clean, thin laces can do to elevate the overall aesthetic of a lived-in boot style 

Military and combat boot styles often feature more tactical or bulky outsoles. Balance the weight and visual impact of a thick sole with a heavier jacket or layered look on top. There’s no denying a combat boot draws attention. Let your combat style boots make a statement. Pair with neutral tones, clean lines and simple garments. Save the pattern play and bold colors for a more subtle and classic boot style like The Pablo.

3. Wearing Work Boots

Classic American work boots grew in popularity in the 90s and have maintained their iconic fashion status for decades. Practical, durable, and wildly comfortable, work boot styles are built to be lived in and design to endure miles and miles of tough wear.

Americana style boots are a versatile style choice that pair well with everything from suits to denim. The Muller boot is inspired by a traditional Americana cap-toe work boot style. The Muller features a rounded toe profile and double stitched capped toe design. The profile is cut close to the ankle for a more tailored fit and feel. The Railroad boot is inspired by a traditional Americana outdoor work boot. Likewise, the Marion, in Olive Chromexcel, features the same round toe last profile and cap toe design. These lace up boot styles carry the rich heritage and aesthetic of Americana with an updated, modern sophistication. In short, they function like a workhorse and look like a show pony.

How to Wear Work Boots

The looks of work boots channels a relaxed style that goes well in almost any setting. You can wear a Muller boot to casual affairs, business situations and parties alike. For smart casual and work wear, chinos would look awesome. Add some extra layering and soft materials to give you the extra pizzazz.

It’s no surprise that denim and work boots are a match made in Americana heaven. Jeans look made for work boots, emanating classic everyman style. The Muller Teak pairs beautifully with Levi’s as the iconic orange seam stitching marries well with the vibrant orange hue of the teak leather 

The Muller’s cap toe profile is often sought after by guests with wider or larger size fits. A cap at the end of a boot’s toe tends to break up the visual impact of larger shoe sizes. It’s a fan favorite for those with a EE width or sizes 12 and up. The Muller runs true to size in D and EE widths.

 We love a Muller boot styled for more formal settings, either with a suit or sports coat. We recommend a light oiling the night before to liven up the leather’s patina. We offer complimentary conditioning at the HELM flagship. If  you ever want to sport a beloved pair of HELM for an upcoming event, come by and see us and we’ll be more than happy to touch them up to have you looking your most dapper.

Some Key Takeaways When to Wear Boots


Styling a pair of handcrafted boots with a suit calls for a few pro tips. Proper tailoring is essential. You will want to be sure the break in your trouser leg is falling in line with the boot vamp. Trousers that are not tapered properly or have an inseam that is overly long will pool at the base of the boot. We suggest taking your favorite pair of boots to your tailor and having your suit trousers tailored to fit. In Texas, cowboy boots with suits is a common practice. It’s not uncommon to see a black tie and boots dress code on a wedding invitation in these parts.

Our favorite leather color to wear with suits is far and away our teak. Teak leather pairs elegantly with navy blue and jewel toned hues. If you’re wearing a color other than black, consider an elevated pair of teak boots. Midnight navy is a great choice for suiting at events, where photography is a priority. Midnight navy is known to photograph beautifully and often reads more luxurious and dimensional in photos than traditional black. Adding a pair of polished and refined boots to a tailored suit can add an unexpected dose of rugged handsomeness. Boots are also a wildly practical choice when attending an outdoor ceremony or event. 

The bestselling HELM boot to pair with men’s suits is easily The Zind Teak. With a minimal and sleek design and beautifully oiled patina, The Zind Teak is elevated and distinctive right out of the box. We often hear guests favor this boot as a groomsman gift. It’s not uncommon to want to step up your wardrobe for a special occasion. A pair of versatile boots looks stylish at the party and lasts as a wardrobe staple for many years beyond.


If you ask us, every occasion needs the right pair of boots. When to wear boots depend on the environment, the dress code, and your own personal style and comfort. Boots are some of the most versatile footwear on Earth. When styled properly, they’ll come along on any adventure.

A good rule for styling boots is: Follow the function. Versatile styles like The Zind are designed to transition seamlessly through an array of environments. With its minimal, tapered toe profile and classic design, The Zind is an ideal fit for almost any occasion. The refined form is a standout choice for smart casual attire. We engineered this boot to take us straight from board meetings to drinks with the team. It’s formal enough to nail the business pitch and causal enough to buy the first round.


In deciding which color leather will pair best with what you already have in your closet, take note of the colors you wear most and feel best in. With its vibrant bourbon hue and natural pull-up patina, Teak leather boots look great with a range of options from denim to navy suits. Brown leather boots and cap toe boots are staple pieces that mix well with a range of casual outfits. Teak leather is often easier to dress up; whereas natural and brown hides tend to read more laid back.

If you have a lot of black in your closet, dark wash jeans, or gray jeans a pair of edited black leather boots compliments a variety of looks. To break up and all black ensemble, try a pair of natural boots. The warm chestnut hue offers a subtle tonal contrast when paired with head to toe black on black garments. 


Invest in craft. Handcrafted footwear built to last through generations of wear is a sustainable choice for the environment that reduces excess and waste while cutting down on your personal cost per wear.

Choosing boots with the highest grade and integrity of hide means your uppers with last longer and contour more fully with wear for a custom fit and feel. All HELM styles are small batched, produced in limited production runs at family-owned and operated facilities we know personally and trust to deliver only the best. Your HELM will only get more and more comfortable with age.

Buying less and wearing more is a sustainable and responsible choice for the environment. It is always our hope your favorite pair of HELM last so long you’ll want to pass them along to the next generation. All our styles are resoleable and handcrafted. Our materials are easy to source and we recommend taking your boots by a reputable cobbler in your area once a year for a wear pattern evaluation. Consulting with a cobbler is a great way to learn how your individual gate, foot shape, and lifestyle effects the longevity and wear pattern of the boot itself. A quality shoemaker or shoe repair shop will be able to not only offer pointers and tips on how to extend the life of your boot, but also make any repairs or resole adjustments in house.


If you’re looking to invest in a single pair of boots that work for any occasion, we suggest starting with either a classic brown or black style. Olive, burgundy, and suede footwear are great for making a statement, but can sometimes be less versatile and more specific. A classic pair of teak leather, black or brown leather boots is an investment piece you’ll wear into the ground.

A classic pair of brown boots is a staple you’re sure to get miles of wear out of. Teak is refined and elevated, easy to transition from casual to more formal settings. Black leather is notoriously the easiest to touch up and keep looking pristine year over year. Know what your top priorities are in terms of style, comfort, and environment and shop accordingly.

Trusty boots are the best companions. A good pair of boots will leave you ready for anything. From work to play, there’s always a pair of HELM to keep you looking and feeling your most confident.

SHOP NOW and get the quality you deserve when it comes to your real leather boots.