best men's dress boots

Best Men's Dress Boots

From wingtips to chukkas to classic brown leather boots, discover which style is best for you…

As an Austin-based small business, when we say we wear boots year round, we mean we’ve got a pair ready for any environment, event, and special occasion. Rain or shine. Day or night. At our Eastside Flagship, we often get asked which styles are the most functional and transitional for more formal settings. If you’re looking for the best men's dress boots to wear to a special occasion, we’ve got you covered. Every pair of HELM is designed to be transitional. Keep reading for our guide to the best dress boot styles and dress shoes…

Why Invest in Craft?

We often hear guests in our store mention they look forward to investing in a good pair of boots for a special occasion for the same reason: They will get more wear out of a good pair of boots than a pair of dress shoes. It’s always fun to upgrade your wardrobe for an event or trip. A beautiful pair of Men’s dress boots is an investment piece that will continue to maintain appeal and value for years to come. Finding the best Men’s dress boots for you is all a matter of assessing your individual style preferences, lifestyle and environment. Let’s start by breaking down the different men’s dress shoe styles available...

Dress Shoe Styles

Dress shoes run the gamut from bold statement to subtle sophistication. Depending on your occasion and sartorial palette, you might find yourself weighing the style benefits of a traditional Oxford shoe, monk strap, derby shoe, loafer or wingtip style. Since there are so many to choose from, we’ll break down each style briefly by noting what makes each dress shoe or casual shoe style special.

Oxford Shoe

A definitive Oxford shoe, often referred to as a brogue, features a shoelace eyelet design that attaches under the vamp. This characteristic is known as “closed lacing.” The main difference between a Derby shoe and an oxford shoe comes down to the laces. In closed lacing, the quarters and side tabs are sewn under the vamp (the front toe part of the shoe). Oxford shoes feature an elongated toe profile with or without a cap toe. The elongated toe profile is a desired companion for traditional tailoring as it tends to cut a sleek and refined form..

Derby Shoe

A Derby shoe features “open lacing,” a design in which the quarters are stitched on top of the shoe’s vamp. Oxfords feature a seam between the tongue and front of the shoe; whereas, derby shoes do not. The looser fitting lace design generally offers a more relaxed, comfortable and contoured fit. A pair of premium leather Derby shoes are easily dressed up or down, able to be worn with a variety of smart casual outfits and suits.

Monk Strap

A Monk Strap shoe is a lace-less style of dress shoe. In lieu of laces, the construction is secured by either one or multiple buckles or straps. Monk strap shoes are generally considered more formal footwear than a Derby shoe, yet still a more casual shoe than a fine leather Oxford shoe.


Another lace-less design, loafers are not always as casual as their name would suggest. When constructed from premium leather and fine material, a loafer is stylish and welcome in both formal and informal settings. The slip on style is easy, transitional and comfortable. We always recommend pairing a no show sock with a pair of leather or suede loafers. The design is frequently worn sock free with trousers, but a no show sock does wonders for preventing blisters and pulling moisture away from the interior of the hide itself.

Wingtip Shoe

An Oxford shoe in which the toecap is extended by “wings” that reach along the side of the shoe is aptly referred to as a wingtip. The cap of the shoe itself is shaped like a W. Wingtip shoes often feature elaborate perforated designs along the toe. A wingtip is historically considered a more casual style; however, wingtip men’s dress boots often transition easily from casual wear to more dressed up occasions.

Cap Toe Shoe

When designing our premiere dress shoe, we wanted to create a shoe with step-in comfort, cushioned insole, and a look that transitioned easily from smart casual to more formal attire. The Bradley is causal and refined, able to be dressed down with a pair of denim or dressed up with a sport coat and tie.

Dress Boot Styles

When it comes to the best men’s dress boots, we’re of the mindset that less is more. A classic leather boot in polished premium leather with a traditional leather sole can be styled a myriad of ways. 

Our favorite dress boot style in the HELM lineup is easily The Zind. With a minimalist design, sleek hardware, and tapered toe profile, this ultra-comfortable staple piece was designed to look effortless and elevated in any room. The Zind Teak is the most asked for casual boot style to be worn dressed up for more formal settings from weddings to parties. It’s also comfortable enough to last through the afterparty…

Chukka boots and Chelsea boots are two boot styles that are easy to dress up with a pair of chinos, wool trousers or tailored suit. Ankle boots styles often feature a lower shaft profile than classic lace up boots or cowboy boots, making them more wearable with any silhouette of pant from slim cut jeans to straight leg trousers. A black leather Chelsea boot is an excellent winter boot style both for its versatility and streamlined, minimalist design. Lace-less boots with a side zipper, such as the HELM Pablo Black, make ideal travel companions and look equally handsome when styled with a suit as simple jeans and a t-shirt. 

Wingtip boots and brogue boot styles are popular dress boot profiles that can be worn with casual wear. A brogue or wingtip typically features a multiple piece upper with decorative perforations known as “broguing.” The construction pieces boast visible edges and often intricate, unique design patterns. If you’re looking for a standout boot to pair with slim fit jeans or a tweed jacket, a brogue or wingtip boot adds old world charm and distinction to smart casual outfits.

Casual Boot Styles

Weatherproof Boots

Weatherproof boots often feature synthetic materials and rubber outsoles. No high quality, full grain leather hide is every completely waterproof. Shoe leather is hot stuffed with a mix of oil and wax as a part of the tanning process. Every tannery features a proprietary mix of different oils and waxes, resulting in a variety of patinas and practical benefits. Weatherproof hides typically feature a higher wax component that allows water to bead off the surface of the leather. Waxing and sealing your boots every few months is an easy way to protect your leather uppers against snow, rain, or chemically salted roads. Additionally, rubber soles are significantly more weatherproof than full leather stack outsoles. A mini-lug, paratrooper or full rubber sole will offer a waterproof seal.

Goodyear Welted Boots

Generally speaking, Goodyear welt construction tends to produce a bulkier design profile. Blake Rapid is largely associated with Fine Italian Footwear construction. The welt of a Blake Rapid shoe is cut closer to the upper than a Goodyear welt, for an aesthetic that reads more streamlined and tailored. Dress boots with Blake Rapid construction and leather soles are timeless and a beautiful addition to any sophisticated wardrobe. There’s a longstanding debate amongst boot enthusiasts and bootmakers alike as to which welt construction type is superior. Both Blake Rapid and Goodyear welts have their advantages. When it comes to dress boots, we’re on team Blake Rapid for the edited precision of the look and easy resoleability of the construction.

Cap Toe Boots

Cap toe boots are sometimes associated with casual boot styles. We hold the position that the cap toe itself does not make the aesthetic more casual, rather cap toe boots often feature a more cumbersome or rounded toe design associated with traditional Americana or work boots (think 1000 miles boots or Iron Rangers). A key differentiator between a pair of work boots and dress boots will be the shape of the toe profile. Dress boots are more tapered in the toe and streamline in the construction, often with less pieces overall to the design. Work boots can feature a round toe box, bulkier laces, more pronounced outsole construction and exaggerated outsole profile.

Cowboy Boots

As a Texas based business, we’re no stranger to Western wear. Cowboy boots are iconic and, in our boot, always in fashion. The slip on profile is designed for roping and riding, with a high shaft, block heel and sturdy toe. Black tie and boots is a whole thing in Texas. If you’re wanting to dress up a pair of Western boots, your best bet is to go with either a high gloss leather or exotic hide. If you find yourself in Austin, the good folks down at Allen’s boots on South Congress have just about any style of cowboy boot you want…

Roper style western boots feature a rounder toe profile. The HELM Pablo Brown takes its inspiration from part Italian Moto boot and part Texas roper style. Our round toe Chelsea boot, the Pablo, is a zip up profile that can be styled with anything from a suit and tie to jeans and a tee shirt. We love it as an alternative to a cowboy boot for a formal Southern gathering.

Moc Toe Boots

Moc toe (short for moccasin) boots are designed with an extra piece of material that extends across the vamp of the shoe down to the toe. The primary objective of a moc toe construction is to protect the toe from injury. Moc toe boots are traditionally associated with work boots for their practical functionality, but have garnered popularity as a casual boot style over the years. The outsole can vary but is always designed for outdoor wear.

The Lou boot to is a fashionable, more dress boot inspired alternative to a moc toe boot. The Lou features a Malt Harrier outsole that is lightweight and optimal for hard surfaces such as pavement or concrete. The last profile is tapered with a cap toe, lending the casual look a bit more polish and flair. The Lou is widely regarded as the most comfortable style in the HELM lineup. Dressed up and polished, The Lou boot is easily styled with nice slacks and sport coats.

How to Pick Your Style

Knowing which dress boot or shoe is right for you comes down to individual style preferences, fit, comfort, and environment. Anytime we’re fitting a guest for a pair of boots in store, we ask after the proposed lifestyle of the boot. Will it be worn outdoors or indoors? Is weatherproofing or traction a concern? How many miles will be walked in the boot or how many hours spent on the dance floor? Is the desired aesthetic a lived in look or pristine patina? We like to think there’s something in the HELM lineup to fit any occasion, wear pattern, and walk of life. Here’s a guide to which styles are best depending on event or environment…

Best Dress Boot Styles for Warm Weather

In Texas, we’re always mindful of the heat. If you’re buying a pair of dress shoes or boots for an outdoor event or party, bear in mind certain profiles are better suited to warm climates than others. For example, desert boots and chukka boots styles were originally designed for military use in hot, desert terrain. A classic suede chukka boot or low profile ankle boot is often lighter weight and more comfortable in the Spring and Summer. With minimal lacing, a low profile desert boot will offer more air circulation and cooling than a traditional lace up wingtip, brogue, or even a cowboy boot.

Best Dress Boot Styles for Outdoor Events

If attending a wedding, concert, or special event in nature, on a ranch, or on mixed terrain, consider dress boot with poured rubber or mini-lug sole construction. Many wingtip or brogue boot styles will feature a full leather bottom sole that can be slick right out of the box. If traction and grip is a concern, make sure your outsoles have poured rubber construction. All HELM boot styles feature an additional rubber component to our leather stack outsole. The Fineline sole reads as a traditional leather outsole from the side, with a poured rubber construction underneath for extra grip out of the box. Don’t worry about slipping on the dance floor in a new pair of HELM. 

If you’re looking to achieve the sophistication and elegance of a dress boot with the flexibility and durability of a work boot, consider The Hollis. With a tapered toe profile (the same last as our dress shoe and dress boots), cap toe, and rugged mini-lug rubber sole, The Hollis is the perfect boot for all seasons. This casual boot design marries the practicality of a work boot and traction of a hiking boot with the precise tailoring and refined toe profile of a dress boot. A cushioned insole and poured rubber sole make it our favorite stylish winter boot in the lineup.

Best Dress Boot Styles for Weddings

The fan favorite for grooms and groomsmen alike at our East Austin shop is The Zind. With a minimal profile and dress shoe last, The Zind is a timeless and stylish boot able to be styled with smart casual outfits, suits, sports coats or jeans and a t-shirt. In Teak Balthazar leather, the rich patina and vibrant hue of the leather pairs elegantly with a navy blue or midnight navy suit. A staple piece that will maintain its appeal for many years to come, a high quality, classic men’s leather boot is an investment sure to be worn well beyond one special occasion.

The Bradley dress shoe and The Declan chukka boot are two low profile styles that are preferred by wedding parties. These styles both feature a cushioned insole for extra step in comfort right out of the box. Low profile desert boot styles boast a minimal break in period due to the flexible tongue design and minimal lacing. First designed for military use in hot climates, a desert or chukka boot in premium leather is a versatile and comfortable choice for special events.

How to Pick Leather Color

Deciding which leather color is best for your dress boots ultimately comes down to your color palette. Rich earthy tones from khaki to chestnut brown and green pair well with chocolate brown boots. Our teak leather boots carry more of a shine out of the box and are beautifully matched with navy blue suits and denim alike. Natural and lighter brown leather boots pair well with all black outfits. Black is always the easiest color of leather to keep looking pristine, even after rough wear.

How to Protect Your Investment

Our goal is always that every pair of HELM boots lasts decades. HELM leather uppers are handcrafted from the finest hides available and will easily last for 15 to 20 years with proper maintenance and typical wear. We personally select every leather salve, boot balm, conditioner, and stain protector product sold on our site and in store. The leather care and boot care products we stock are an optimal match for our hides. All HELM leather boots and shoes are made from exclusively cow hides of the highest grade and integrity. We recommend consulting a reputable cobbler or your local bootmaker before conditioning exotic leathers or exotic hide boots. That said, you can always rest assured the products sold at HELM are the best available treatments for our unique leather boots and suede shoes.


Consulting with a good local cobbler is the best way to evaluate your individual wear pattern and evaluate how to extend the life of your boot soles. How to know when to resole your boots comes down to a variety of factors. Everything personal lifestyle, frequency of use, climate, and even individual gate and body weight can affect the longevity and wear pattern of a boot. Rotating out your boots every 3 to 4 days is best practice. Rotating styles protects the muscles in your feet from becoming overly fatigued in one profile in addition to extending the life of your outsoles.

All HELM boots and shoes are able to be resoled with any outsole option in our lineup. Additionally, our materials are easy to source and a full resole or heel replacement is a simple undertaking any reputable cobbler in your area should be able to complete for you. Most people see the brunt of wear on the back heel of their boots. Our rubber key design is easy to replace for a small fee (usually around $15). Replace your rubber key heels before your wear pattern grinds into the leather stack and you’ll be good to go.

Leather Conditioning

High quality leather requires intermittent maintenance and conditioning. Leather is a natural material and the life of the hide is extended with regular leather conditioning treatment such as a boot balm, leather salve, mink oil, or shoe grease. Our favorite product for simple everyday upkeep is Blackrock Leather N’ Rich. Applying a light coat of Blackrock to your leather uppers every six months is enough to keep your boots looking handsome and protected. If you live in severe or inclement climate, weatherproofing your leather boots and leather shoes is always a wise practice. Boot wax and sealant used with a regular leather conditioner will help extend the life of wear and protect your leather uppers from rain, snow, chemical salts or even sweat.

To read more on how to take care of your leather boots, read our leather maintenance guide!

Shining and Scuffs

Leather is hot stuffed with a mix of oils and waxes during the tanning process. Tanneries develop unique recipes to achieve distinctive patinas and aesthetics. Different blends of oils and waxes used in the tanning process will determine how the boot with show character variance with wear, what the pull up will look like, and how the leather itself will look fresh out of the box.

If you’re looking to shine or remove scuffs from leather boots or shoes to bring them back to their original luster for an event, investing in a simple boot care kit is typically all that’s required. We favor Venetian Leather Balm and Blackrock for touching up scuffs, scratches, or polishing the patina of our hides. When using a leather conditioner or shoe shine product, always spot test first on the inner corner of the heel before applying to the whole boot or shoe. Make sure the desired effect is what you’re looking for before you condition your best loved pair. Some leather conditioner and leather oil may deepen or alter the original patina of a boot.

The best Men’s dress boots for you are the ones you’ll never want to take off. Optimizing fit and comfort comes down to a number of factors, from last profile to leather type and lifestyle. When you invest in a quality pair of men’s leather dress boots, a bit of maintenance and everyday care will protect your footwear against the elements and normal wear and tear. Check out the HELM Boot Care blog for more tips on conditioning and daily maintenance…from our favorite leather care products to waterproof sprays and boot wax.

A pair of the best men's dress boots from HELM certainly would be a great addition to your closet, no matter how many other kinds of footwear you already have in your wardrobe. Shop more.

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