Dress boots for men have become one of the most essential types of boots in both formal and casual looks. As we enter 2023, new trends are emerging that combine timeless style with modern designs and innovative materials. This guide will explore everything you need to know about selecting the ideal dress boots to elevate your wardrobe this year.
What Are Dress Boots?
Dress boots refer to boots that can be worn with formal attire or business casual looks. As opposed to work boots or winter boots designed for heavy-duty use, dress boots focus more on aesthetics and styling over rugged functionality.
Men’s dress boots first became popular in the mid-19th century when gentlemen favored riding boots translated into fashionable footwear. Today’s dress boots for men have evolved to include sleek silhouettes, premium leather materials, and elegant accents that perfectly balance eye-catching style with versatility and comfort.
Top 6 Dress Boots for Men in 2024
| Boot Type | Brand | Key Features | Price | Sizes | Colors |
|---|---|---|---|---|---|
| Best Chelsea Boot | Common Projects | Suede Chelsea Boots, Italian suede, elastic gore side panels, classic silhouette, crepe rubber sole, leather lining | $495 | EU 36-46 | Sand, Tobacco |
| Best Chukka Boot | Wings + Horns | Hi-Top, Japanese leather, suede accents, zip closure, rubber lug sole, padded leather lining | $545 | 7-13 | Black, Brown |
| Best Brogue Boot | Grenson | Fred Triple Welt, pebble grain leather, intricate broguing, contrast triple welt trim, Goodyear welted, rubber sole | $575 | 7-13 | Tan, Black |
| Best Wingtip Boot | Allen Edmonds | Dalton Wingtip Dress Boots, calfskin leather, brogue detail, leather lining, double leather sole, made in USA | $695 | 7-15 | Black, Walnut |
| Best Monk Strap Boot | Magnanni | Kios Double Monk Strap, Spanish calfskin, double buckle straps, cap toe, Blake rapid construction, rubber/leather sole | ? | ? | ? |
Best Chelsea Boot: Common Projects Suede Chelsea Boots
- Ultra-soft Italian suede upper
- Elastic gore side panels
- Classic Chelsea silhouette
- Crepe rubber sole
- Also available in smooth leather
These Italian-made Chelsea boots from Common Projects bring the brand’s characteristic minimalist luxury to an ankle-high boot silhouette. Crafted from premium Italian leather with elastic side gores, these boots strike an ideal balance between timeless and modern. The sleek shape showcases impeccable clean lines from toe to heel counter for an elegant side profile. With a heel measuring just 1.25 inches, they remain versatile enough for all-day wear. A leather lining creates a smooth slip-on interior, while the leather outsole provides both durability and traction. The Common Projects polished design pairs perfectly with tailored trousers as well as casual weekend wares.
| Price | Sizes | Colors |
|---|---|---|
| $495 | EU 36-46 | Sand, Tobacco |
Best Chukka Boot: Wings + Horns Hi-Top Chukka Boot
- Japanese leather upper
- Contrast color suede accents
- Exposed zip closure
- Rubber lug sole
- Padded leather lining
When it comes to chukkas, Wings + Horns is soaring above the competition with their sick hi-top version. They start with rich Japanese leather then detail it out with custom indigo suede around the collar – instant outfit transformer! I’m obsessed with the stealth black zipper closure keeping things sleek while lugged soles and padded ankles banish blisters for all-day exploration. Whether you’re hitting the trail or bar hopping, these will have you looking fly while standing up to anything your adventurous lifestyle dishes out. The combo of quality construction, unique style, and urban explorer spirit makes these the prime contenders for the best chukkas out there!
| Price | Sizes | Colors |
|---|---|---|
| $545 | 7-13 | Black, brown |
Best Brogue Boot: Grenson Fred Triple Welt Brogue Boots
- Pebble grain leather upper
- Intricate broguing details
- Contrast triple welt trim
- Durable rubber sole
- Goodyear welted
Grenson’s Fred brogue boot takes a traditional style to new levels of intricacy. Built from pebble grain leather for added depth, the upper features the expected perforated trim details across toe caps, eye stays, and heel counters. But Grenson doubles down by adding an ornate triple welt line accent that reveals contrasting hues on the outsole and heel. Despite the embellishments, quality craftsmanship ensures long-term durability thanks to components like the Goodyear welted construction and sturdy rubber sole. Alternating tan and black triple welt colors enable visual distinction whether paired with denim jeans on weekends or wool trousers at the office.
| Price | Sizes | Colors |
|---|---|---|
| $575 | 7-13 | Tan, Black |
Best Wingtip Boot: Allen Edmonds Dalton Wingtip Dress Boots
- Hand-crafted calfskin leather
- Perforated brogue wingtip detail
- Leather lining
- Double leather sole
- Made in USA
Allen Edmonds builds upon their reputation for expert artisanal quality with the Dalton wingtip boot. It starts with hand-selected calfskin leather cut, stitched, and finished by master craftsmen in Port Washington, Wisconsin. The upper features classic broguing perforations across the cap toe, heel counters, and eye stays. Distinctive wingtip toe caps extend along the toe boxes with pointed panel peaks resembling wings. Contrast welt stitching and edge dressing provide subtle decorative touches. The boots also incorporate components like a leather lining that forms to feet over time. Meanwhile, the double leather sole offers traction indoors and grip outdoors. So whether styled with a power suit or casual button-down and jeans, the Dalton delivers bold distinction.
| Price | Sizes | Colors |
|---|---|---|
| $695 | 7-15 | Black, Walnut |
Best Monk Strap Boot: Magnanni Kios Double Monk Strap Boot
- Spanish calfskin leather
- Double buckle monk straps
- Sleek cap toe
- Blake rapid construction
- Rubber and leather sole
Magnanni translates the decorative monk strap closure of traditional dress Oxfords into a refined ankle boot. Built in Almansa, Spain using rich Spanish calfskin leather, the streamlined silhouette focuses attention on the twin buckled straps crossing the laced upper. Sleek toe caps contrast against the supple leather surrounding them. Blake’s rapid construction allows for the absence of an insole board for increased flexibility and lightness. The boots balance desk-to-dinner versatility thanks to a combination of rubber and leather sole. So whether paired with crisp suit pants or dark rinse denim, the Kios double monk strap boot strikes sophistication from boardroom meetings to cocktails at the bar.
| Price | Sizes | Colors |
|---|---|---|
| $450 | 7-15 | Black, Brown |
Different Types of Dress Boots
| Boot Style | Material | Style Notes | Best For |
|---|---|---|---|
| Chelsea Boots | Leather/Suede | Slip-on, elastic side panel | Casual to semi-formal |
| Chukka Boots | Suede/Leather | Ankle-high, open lacing, 2-3 eyelets | Casual wear |
| Brogue Boots | Leather | Perforations, wingtip design | Business casual to formal |
| Monk Strap Boots | Leather | Buckle closure, no lacing | Unique, formal settings |
| Ankle Boots | Leather | Short lacing, versatile style | Everyday wear |
| Balmoral Boots | Leather | Closed lacing, formal design | Formal occasions |
Chelsea Boots
Chelsea boots originated in mid-19th century Britain when Queen Victoria’s shoemaker, J. Sparkes Hall, designed the first elastic-sided boots for the Queen.
By the 1960s, Chelsea boots became popular amongst British mods and musicians like The Beatles and The Rolling Stones began sporting the style. Today, Chelsea boots are considered one of the most versatile men’s boot styles, seamlessly straddling both formal and casual looks.
Key Characteristics:
- Ankle-high boots with elastic side panels
- Pull-on construction without laces or buckles
- Often made of leather; suede is also popular
Chelsea boots are ideal for business casual office environments. Their minimalist, clean-lined look elevates everything from jeans and a button-down to a full suit. Their elastic sides also make Chelsea boots easy to take on and off when passing through airport security.
Read this article if you want to learn more about styling Chelsea boots.
Chukka Boots
Chukka boots, also known as desert boots, are ankle-high boots with eyelets/lace-up construction. They are characterized by their minimal 2-3 eyelet open lacing system.
This style first emerged in the 1940s when British soldiers returning from Egypt and Libya brought back this lightweight, breathable style. The name “chukka” comes from the game of polo, where a chukka is a single period of play.
Key Characteristics:
- Ankle-height construction
- 2-3 eyelet open lacing
- Made of suede or leather
- Open lacing provides versatility
Chukka boots easily transition from day to night with everything from dark denim, chinos, and dress pants to even suits. Opt for suede chukkas paired with an unstructured blazer and shirt for an elevated casual look. For dressier occasions, smooth leather provides a refined touch.
Ankle Boots
Ankle boots refer to any boot with a shaft height that ends just above the ankle bone, offering more versatility than taller boots. They come in both dressier Cuban heel varieties along with rugged lugged sole workwear styles.
By the late 1960s, high-heeled ankle boots became popular thanks to French designer Andre Courreges. Throughout the decades, designers like Marc Jacobs and Thom Browne have created their takes on the iconic silhouette.
Key Characteristics:
- End just above the ankle bone
- Come in both block and high-heel varieties
- Range of versatility depending on heel height and material
- Allows pants to be worn over or tucked in
Ankle boots effortlessly bridge the gap between casual days and nights out. Pair Chelsea ankle boots with cropped trousers or a flared midi skirt. Chunky lugged soles work well with distressed denim and flannels.
For a modern twist on the iconic Beatle boot, opt for a Chelsea ankle boot with a subtle block heel. Storm-welted leather lends a balance of rockstar edge and refinement.
Brogue Boots
Brogue boots take the decorative perforations and serration details (or broguing) characteristic of classic brogue shoes and translate them onto ankle, Chelsea, and Chukka boot silhouettes.
These boots originated from traditional Scottish Highland shoes that had perforated decorations allowing water to drain. By the 20th century, brogueing became a distinguishing feature of Oxfords and other formal shoes. Applying this embellished touch to boots created an intersection of refinement and ruggedness.
Key Characteristics:
- Decorative perforations along the leather upper
- Wingtip toe caps with serrated edges
- Cap toes with medallion accents
- Broguing combined with boot silhouettes
Brogue boots allow gents to add visual interest and sophistication to outfits from business suits to casual weekend wear. Pair wingtip brogues with bold socks and cuffed trousers or jeans for an eye-catching touch. Opt for full brogue boots in rich burnished leather to complement an autumnal aesthetic.
Monk Strap Boots
Monk strap boots feature one to four buckled straps across their upper in place of traditional lace closures. The name comes from medieval Catholic monks who donned sandals secured by straps.
By the 17th century, the monk strap emerged as a decorative feature on dress shoes. Translating the monk strap onto ankle boots created unique statement-makers that bridge ruggedness with refined detailing.
Key Characteristics:
- Buckled strap closures across the upper
- Rounded, pointed, or squared toebox
- Made of smooth or grained leather
- Often feature cap toes and medallions
Double monk strap boots feature two buckled straps, allowing guys to refine casual fits like chinos, opened-collared shirts, and blazers with eye-catching — yet still sophisticated — footwear. For black tie and formal events, single monk strap boots in patent leather complement classic tuxedos flawlessly.
Wingtip Boots
Applying the iconic wingtip style seen on brogues and Oxfords onto boots results in statement styles that seamlessly transition from tailgates to date nights.
Wingtips feature toe caps with pointed extensions that resemble wings. When translated onto boots ranging from Chelsea to Chukka to lace-up, they create dress options rooted in menswear tradition yet feel completely fresh.
Key Characteristics:
- Signature winged toe caps
- Contrasting toe caps, heels, and soles
- Traditional broguing and medallion details
- Created on a range of boot silhouettes
Wingtip boots dominated street style trends thanks to their eye-catching characteristics. The punchy toe caps pair perfectly with casual tailored separates. For more formal affairs, the wedge soles provide subtle height boosts.
Read more about Oxford Boots vs Wingtip Boots.
What Makes a Dress Boot Stand Out?
So what sets dress boots apart from other boot styles? The key is in the finer details of construction and design.
Key Features of High-Quality Dress Boots
- Premium Materials – The highest quality men’s dress boots utilize leather hides such as calfskin, suede, nubuck, patent leather, and exotic skins like ostrich and alligator. These materials provide flexibility, durability, and a luxurious look and feel.
- Skilled Construction – Shoemaking techniques like Goodyear welting and Blake stitching are used to attach the upper part of boots to the sole for maximum stability and weatherproofing. This allows the boots to handle wear and tear over years of use.
- Attention to Detail – From the number and placement of eyelets and speed hooks to the thread utilized, every element of fine dress boots is meticulously crafted. Even the outsoles are leather or high-grade rubber for traction, flexibility, and style.
Style and Design Variations
Beyond construction, the aesthetics of dress boots also set them apart, including:
- Boot Height – Ranging from sleek ankle-height boots to boots reaching mid-calf, the height provides different levels of coverage and visual impact.
- Boot Silhouette – From slip-on Chelsea boots to lace-up bluchers and oxfords, the side profile affects the overall look.
- Toe Shape – Pointed, rounded, or square toe shapes change the boots’ style significantly.
- Accents – Cap toes, medallions, broguing, and buckles add ornate touches.
- Color – Available in neutral, earth tone, pastel, and eye-catching shades.
- Finishes – Matte or polished leather, rugged suede, glossy patent leather – all create distinctive looks.
Now that you understand the key characteristics that set dress boots apart, let’s explore some of the most popular styles.
How to Style Dress Boots
Dress boots offer versatility that allows them to seamlessly transition from formal occasions to laid-back looks. Here’s how to sport them for everything from black tie events to weekend errands.
For Formal Occasions
The refined silhouettes and fine materials of dress boots make them the perfect footwear finishing touch for formalwear. Consider these tips when incorporating them into black tie or smart casual looks:
- Play with Texture Contrasts – Patent leather or smooth matte leather boots pop against textured suit fabrics like hopsack, linen, or velvet.
- Complement Colors – Choose boot colors that coordinate with your suits and formalwear rather than compete. Black and oxblood boots are foolproof options.
- Focus on Fit – Sleek Chelsea or minimalist lace-up boots keep lines clean and emphasize tailoring versus distracting with overt designs.
- Elevate Monochromatic Looks – Allow bold boots to serve as a neutral color’s highlight. Camel boots add interest to off-white and tan suits.
Casual & Business Casual Settings
Dress boots also feel right at home paired with casual essentials like jeans to create smart weekend looks.
- Contrast Textures – Rugged suede desert boots work well with worn-in denim and flannels.
- Lean into Seasonal Color Trends – Rich emerald boots connect to jewel-toned fall hues. White boots pop against darker neutrals.
- Play with Proportions – Bulkier Iron Ranger-style boots balance cropped trousers and oversized sweater layers.
- Show Some Skin – Distressed and waxed suede chukkas complement exposed ankles.
Seasonal Styling Tips
As the calendar changes, adapt your boots with tips like:
Spring/Summer:
- Swap in fabric Chelsea boots for warmer temps
- Contrast against linen suits and camp collar shirts
Fall/Winter:
- Incorporate boot socks into layered looks
- Allow wool trousers to puddle over leather or suede boots
- Waterproof leathers stand up to weather and add sleek visual contrast against puffer jackets
How to Choose the Right Dress Boots
Consider these factors when selecting your next pair of dress boots for maximum satisfaction.
Fit and Comfort
- Know Your Size – Common sizing systems include US, EU, and UK — be sure of your translation before purchasing.
- Prioritize First Steps – Leather will stretch and suede will relax over time, but first wear should feel secure in the heel and toe box.
- Consider Width – Wide calf shafts, adjustable buckles and laces, and generous toe boxes provide comfort options.
- Insoles are Key – Well-cushioned and moisture-wicking insoles, as well as customized orthotic inserts, elevate comfort.
Matching with Your Wardrobe
Choose boots that fill current gaps in your closet, including:
- Seasonal Needs – Lightweight suede for spring and summer; rugged, weatherproof leathers in fall and winter.
- Formal Versus Casual – Finesse finishes for black tie looks; more distressed leathers for laid-back layering.
- Statement Versus Subtle – Eyecatching monk straps or metallic Chelsea boots serve as accessories; neutral suede blends seamlessly.
- Experiment with Silhouettes – Start with versatile ankle heights then explore options like cowboy-cut or over-the-knee.
Care and Maintenance of Dress Boots
Investing in quality men’s dress boots means properly caring for them as well. Here are tips to maximize their lifespan:
Cleaning and Conditioning
- Banish Scuffs – Gently buff away surface scuffs with a horsehair bristle brush. Use a damp rag for stuck-on debris.
- Clean Oils and Stains – Mix mild dish soap with warm water. Lightly scrub the stained area with a towel, then wipe clean with a rag. Allow to fully dry.
- Condition Leather – Apply leather conditioner or cream with cloth and buff gently. This maintains flexibility and moisture.
- Weatherproof Suede – Use suede protector spray to repel water and stains. Reapply every few months.
- Heal Heels – Rub heel edges on sandpaper to smooth over. Buff with heel balm or wax to condition.
Long-Term Storage
- Chest It – Store boots upright in breathable shoe trees inside the closet when possible to retain shape. Cedar absorbs moisture which can warp leather when boots are packed away.
- Give Space – If necessary box up boots, stuff boots with acid-free tissue paper, and leave them unsealed. Tight boxes lead to deterioration over time.
- Avoid Extremes – Leather can become brittle in very cold spaces. Excessive heat from radiators and direct sunlight causes boots to dry out.
Where to Buy Dress Boots for Men
Quality dress boots are investments, so ensure reputable retailers. Look to specialty online shops along with classic department stores like Nordstrom and Saks Fifth Avenue. Some top options include:
- Mr Porter – Extensive luxury styles.
- Allen Edmonds – Known for Goodyear-welted craftsmanship.
- Wings + Horns – Directionally oriented luxury footwear.
- Thursday Boot Co. – Direct-to-consumer quality at lower prices.
Conclusion
Distinguishing the array of men’s dress boots available today empowers gents to select their perfect pair to complement formal, business, and casual looks alike.
Understanding construction quality, popular styles like Chelsea and chukkas, and proper care regimens helps build smart footwear investments. Most importantly, embrace boots that feel uniquely you and elevate your flair. The options ahead are all sole-satisfying.
Frequently Asked Questions
Can You Wear Boots with Formal Dress for Men?
Yes, boots can be a stylish and appropriate choice for formal wear for men. The key is to choose sleek, well-polished dress boots in classic colors like black or brown, which can complement a formal outfit effectively.
What Boots Are Considered Formal?
Formal boots are typically characterized by their refined design, high-quality materials, and polished finish. Classic styles like Chelsea boots, Chukka boots, and especially those with minimalistic designs and darker colors are often considered suitable for formal occasions.
Is It Okay to Wear Dress Boots with a Suit?
Absolutely. Dress boots pair well with suits and can offer a sophisticated, slightly edgy look. Ensure the boots are well-polished and the color matches or complements your suit. Slimmer boot profiles tend to blend better with the streamlined look of a suit.
What Makes a Boot ‘Dressy’?
A ‘dressy’ boot is distinguished by its sleek profile, finer leather construction, minimalistic design, and polished finish. Details like fewer seams, elegant lines, and the absence of bulky hardware contribute to a dressier appearance.
Can I Wear Ankle Boots with a Formal Dress?
While this question seems more relevant to women’s fashion, in men’s fashion, wearing ankle boots with formal attire is indeed acceptable. Ankle boots can be a stylish choice for formal events when chosen correctly. Opt for a clean, sleek design in a color that matches or complements your formal attire.
