The 25 Most Comfortable Heels for Long Walks in the City

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Stepping out in style doesn't have to mean sacrificing comfort. In the bustling cityscape, where every step counts and every stride takes you closer to your destination, the right pair of heels can make all the difference. This article delves into the world of fashion-forward yet comfortable footwear, highlighting the 25 most comfortable heels perfect for long walks in the city. Whether you're navigating cobblestone streets, dashing between meetings, or exploring urban landscapes, these heels promise to keep you elevated in both style and comfort. Get ready to discover how you can add a touch of elegance to your every step, without the usual discomfort associated with high heels. Let's explore these city-friendly wonders that blend chic design with practical wearability.

1. Elegant Strappy Elegance: ASOS DESIGN's Mid-Heeled Tie-Leg Sandals

Experience the unique elegance of ASOS DESIGN's Hollow strappy tie-leg mid-heeled sandals. The innovative tie-leg design and lace-up fastening allow for a customizable fit, catering to various foot sizes with ease. The peep toe element introduces an element of chic sophistication, making these sandals a versatile option for both professional environments and relaxed occasions. The mid-block heel provides a subtle lift, ideal for navigating the city streets with ease. Crafted from smooth faux-leather, these sandals boast a polished appearance, fitting for any summer event or as part of your daily office attire. More than just footwear, these sandals are a statement of fashion, designed for durability and extended wear.

Price: $17 | Buy on Asos

2. Elegance Unveiled: Mariee Light Nude Pointed-Toe Pumps

The Mariee Light Nude Pointed-Toe Pumps are a quintessential choice for the woman seeking a blend of sophistication and comfort in her footwear. These pumps feature a sleek, smooth faux leather construction that embodies a classic and professional look, perfect for office meetings or elegant evenings out. The pointed-toe design adds a touch of refined grace, enhancing the shoe's overall stylish and trendy appeal. A 3-inch wrapped stiletto heel offers just the right amount of elevation, providing a comfortable walking experience without sacrificing the elegance of a high heel. The cushioned insole ensures all-day comfort, making these pumps ideal for those long strolls in the city. Whether paired with formal attire or a casual ensemble, these pumps are a versatile addition to any wardrobe, promising to elevate your style with their timeless charm and comfort.

Price: $20 | Buy on Lulus

3. Almond Elegance: Myra Strappy Stacked Heeled Sandals

The Myra Strappy Stacked Heeled Sandals in almond are the epitome of comfort and style, perfect for those long walks in the city. These sandals feature a comfortable 2.5" stacked heel, offering a modest elevation while maintaining stability and ease of movement. The design boasts a chic square open toe and elegant faux leather straps, complete with buckles that add a fashionable touch and ensure a secure fit. The padded footbed is a standout feature, providing extra cushioning to support your feet throughout the day. These sandals are not only stylish but also practical, making them a versatile choice for various occasions, from a casual day out to a more formal event. Their trendy and classy design, coupled with the comfort they provide, makes them a must-have in any fashion-forward woman's wardrobe.

Price: $34 | Buy on Vicicollection

4. Sleek Sophistication: NA-KD's Pointy Black Pumps

The NA-KD Pointy Pumps in classic black are a staple for any fashion-savvy woman looking for a blend of elegance and practicality. These pumps feature a sleek pointed toe and a slip-on design, making them both stylish and convenient for everyday wear. The unique hourglass heel, standing at a comfortable height of 8 cm (3.15 in), offers a modern twist to the traditional stiletto, providing a chic look while ensuring stability during long city walks. The polyurethane composition gives these shoes a polished finish, suitable for professional settings or evening events. These pumps are not just footwear; they are a statement piece that can elevate any outfit, whether it's for a day at the office or a night out. Their timeless design and comfortable fit make them a versatile and essential addition to any wardrobe.

Price: $45 | Buy on Na-kd

5. Blush Elegance: ASOS DESIGN's Placid High Block Heels

The ASOS DESIGN Placid high block heels in blush are the epitome of comfort and style for the modern woman. These shoes feature a soft faux-suede upper that adds a touch of luxury and elegance, perfect for office wear or a classy evening event. The high block heel paired with a supportive platform sole ensures comfort and stability, making them ideal for long walks in the city. Their round toe design and pin-buckle fastening provide a secure and comfortable fit, catering to a wide range of foot sizes. These heels are not only stylish but also offer practicality and durability, making them a must-have in any woman's wardrobe. Whether you're attending a summer party or a formal meeting, these heels promise to elevate your look with their trendy and professional appeal.

Price: $17 | Buy on Asos

6. Classic Charm: Marny Black Patent Low Heel Ballet Pumps

The Marny Black Patent Low Heel Bow Ballet Pumps are a delightful blend of classic style and modern comfort. Crafted with shiny faux patent leather, these pumps exude a sleek and elegant look, perfect for both office and casual wear. The standout feature is the charming bow detail with gold aglets on the vamp, adding a touch of femininity and sophistication. These shoes are designed with a squared-toe and a low-cut collar, creating a silhouette that's both trendy and timeless. The slip-on design ensures ease of wear, making them a practical choice for busy women. With a comfortable 1.75" wrapped block heel, these pumps are ideal for long city walks, providing both style and comfort without compromising on either. These ballet pumps are not just footwear; they are a statement of refined taste and effortless grace.

Price: $44 | Buy on Lulus

7. Modern Chic: ELLIE Mary Jane Heels in Black Patent

The ELLIE Mary Jane Heels in Black Patent are a modern twist on a classic style, perfect for the fashion-forward woman. These heels feature a glossy faux patent leather loafer design that exudes a sleek and professional look, ideal for office attire or sophisticated events. The platform base and treaded sole offer both comfort and stability, making them suitable for long walks in the city. The single strap upper with silver-toned hardware and buckle fastening adds a touch of elegance while ensuring a secure fit. These heels are not just about style; they also provide the practicality needed for everyday wear. The combination of their trendy design, comfortable platform, and durable materials makes them a versatile and essential addition to any contemporary wardrobe.

Price: $70 | Buy on Princesspolly

8. Beige Beauty: Kassia Vegan Leather Strappy Sandals

The Kassia Vegan Leather Sandals in Tahini Beige are a testament to sustainable fashion without compromising on style. These sandals feature an elegant strappy design, crafted entirely from high-quality beige vegan leather, making them not only stylish but also environmentally conscious. The sculpted stiletto heels add a touch of sophistication and are perfect for confident strides, whether at an evening event or a day out. Their barely-there silhouette flatters the foot, offering both a sexy and elegant look. These sandals are more than just footwear; they're a fashion statement that combines comfort, ethics, and style. Ideal for the modern woman who values both aesthetics and sustainability, these sandals are sure to become a cherished addition to your wardrobe.

Price: $70 | Buy on Fordays

9. Pretty in Pink: Chiko Kimberlyn Square Toe Block Heels

The Chiko Kimberlyn Square Toe Block Heels Pumps in a delightful pink shade are a chic and comfortable choice for the fashion-forward woman. These pumps feature a trendy square toe design, combining modern aesthetics with a classic feel. The approximately 6 cm block heels offer a comfortable lift, perfect for long walks in the city while maintaining an elegant posture. The rubber sole adds practicality, ensuring stability and ease with every step. These pumps are not only stylish but also versatile, making them suitable for a range of occasions, from a day at the office to an evening out. Their blend of comfort and style makes them a must-have addition to any wardrobe, offering a pop of color and sophistication.

Price: $105 | Buy on Chikoshoes

10. White Wonder: ASOS DESIGN's Highway Chunky Mid Heel Sandals

The ASOS DESIGN Highway chunky mid heel sandals in white are a perfect fusion of style and comfort for the active city woman. These sandals boast a smooth faux-leather upper, offering a sleek and professional look suitable for both office and casual wear. The mid block heel provides the perfect height for comfort, making them ideal for long walks around the city. With a pin-buckle fastening, they ensure a secure and adjustable fit, accommodating a variety of foot sizes with ease. The chunky sole not only adds to their trendy appeal but also offers additional support, making every step feel comfortable and stable. Whether you're dressing up for a summer party or dressing down for a casual day out, these sandals are a versatile and stylish choice that combines functionality with fashionable design.

Price: $15 | Buy on Asos

11. Elevated Elegance: Diligent Light Nude Patent Platform Pumps

The Diligent Light Nude Patent Ankle Strap Platform Pumps are a perfect match for those who cherish both style and comfort in their footwear. These pumps feature a sleek faux patent leather composition, offering a polished and sophisticated look suitable for a variety of occasions, from office to evening events. The design incorporates a stylish square-toe and a practical 0.75" toe platform, balancing fashion with comfort. The ankle straps, adorned with shiny gold buckles, not only add a touch of elegance but also ensure a secure and adjustable fit, accommodating different foot sizes with ease. The 3.5" wrapped block heel provides a comfortable lift, while the cushioned insole and nonskid rubber sole make these pumps a reliable choice for long city walks. These platform pumps are more than just shoes; they are a statement of refined taste and practical elegance, effortlessly enhancing any outfit.

Price: $26 | Buy on Lulus

12. Chic Contrast: Suede Color Stitching Chunky Heel Mary Janes

The Suede Color Contrast Stitching Classic Chunky Heel Mary Jane Shoes in Off White and Apricot offer a stylish twist on a timeless design. These elegant Mary Janes feature a striking color block pattern, set in soft faux suede and PU, that adds a touch of sophistication to any outfit. The adjustable buckle closure ensures a comfortable and secure fit, making them ideal for all-day wear, whether you're commuting or engaged in daily activities. The chunky heel provides a comfortable height, perfect for those who want elevation without sacrificing stability. The closed, square toe design coupled with features like breathability and non-slip soles make these shoes not just fashionable but also practical and comfortable for long walks in the city. Their unique style and comfortable build make them a versatile choice for any season, suitable for both professional and casual looks.

Price: $41 | Buy on Stylewe

13. Sparkling Charm: NA-KD's Glittery Ankle Strap Heels

The NA-KD Glittery Ankle Strap Heels are a dazzling addition to any fashion-forward wardrobe. These heels feature a striking glittery design on a black background, perfect for adding a touch of glamour to any outfit. The block heel, standing at a comfortable height of 8.5 cm (3.6 in), provides stability and ease, making them ideal for long walks in the city. The open heel design and square peep toe add a modern and stylish flair, while the strap detail with buckle closure ensures a secure and adjustable fit. These heels are not just a fashion statement but a practical choice for various occasions, from a night out to a formal event. Their combination of style, comfort, and versatility makes them a must-have for any woman seeking to elevate her look with a unique and eye-catching pair of shoes.

Price: $52 | Buy on Na-kd

14. Classic Charm: CHIKO Terica Round Toe Block Heels

The CHIKO Terica Round Toe Block Heels Mary Jane Shoes in White are a timeless addition to your shoe collection, perfect for those who appreciate classic style with a modern twist. These Mary Janes feature a luxurious leather upper and lining, ensuring both comfort and quality. The rubber sole offers practicality and durability, ideal for navigating city streets. The heel height of approximately 2.5 inches (6 cm) strikes the perfect balance between elegance and comfort, making them suitable for both work and casual outings. Their minimalist design with a color pop of white makes them a versatile choice for any outfit, embodying a blend of simplicity and sophistication. These shoes are a must-have for the fashion-conscious woman, offering both style and comfort in a chic package.

Price: $125 | Buy on Chikoshoes

15. Chic Elegance: RAID Maya's Embellished Block Heel Mary Janes

The RAID Maya block heel mary janes are a stylish embodiment of comfort and elegance. These shoes, with their sleek black patent faux-leather upper, are a sophisticated choice for the woman who values both fashion and functionality. The adjustable ankle strap with a pin-buckle fastening provides a customizable and secure fit, ensuring comfort for a variety of foot sizes. The square toe design adds a modern twist to the classic mary jane style, making these shoes a perfect match for both formal and casual attire. The high block heel offers a comfortable lift, ideal for long walks in the city while maintaining a professional and trendy look. Whether heading to the office or attending a party, these mary janes offer a blend of luxury and practicality, making them a must-have in your footwear collection.

Price: $31 | Buy on Asos

16. Glamorous Stride: Luna Light Nude Suede Lace-Up Heels

The Luna Light Nude Suede Lace-Up Heels are essential for those seeking contemporary style. Their velvety faux suede and pointed toe design radiate sophistication and trendiness. The lace-up vamp, highlighted by gold aglets, adds a distinctive, fashionable flair, perfect for any party or social event. With a 4" wrapped block heel, these heels provide a comfortable lift, suitable for extended periods of urban exploration or daily activities, all while maintaining a chic and glamorous look. The lightly cushioned insole and felted rubber sole with nonskid markings combine comfort with safety, making these heels practical for regular use. Ideal for an evening out or professional settings, these lace-up heels are a versatile and elegant addition to any wardrobe, seamlessly merging style with practicality.

Price: $16 | Buy on Lulus

17. Velvet Elegance: FARRINGTON Black Heels

The FARRINGTON Heels in Black offer a luxurious touch to any outfit with their sumptuous velvet upper, perfect for those who appreciate a blend of elegance and contemporary design. These heels stand out with a wide strap upper, combining style with a secure and comfortable fit. The block heel and platform base not only add to their chic appearance but also ensure stability and comfort, ideal for navigating city streets with ease. The 9cm (3.5in) heel height provides the perfect lift, enhancing your silhouette while maintaining comfort for extended wear. Whether you're heading to a formal event or a day at the office, these heels are a versatile choice, offering both luxury and practicality. Their stylish design and comfortable build make them a must-have in any modern wardrobe.

Price: $30 | Buy on Princesspolly

18. Sleek Elegance: NA-KD's Glossy Pointy Toe Pumps

NA-KD's Glossy Pointy Toe Pumps are the epitome of sleek sophistication. These black pumps boast a lustrous glossy finish, perfect for adding a polished touch to any outfit. The pointed toe design exudes a chic and fashionable appeal, making them an ideal choice for office wear or sophisticated evenings out. The ankle-strap fastening, complete with an adjustable buckle, ensures a secure and customizable fit, adding both style and functionality. The 9 cm (3.54 in) hourglass heels provide a comfortable elevation, perfect for long walks around the city without compromising on elegance. These pumps are not just a stylish accessory but a versatile addition to any wardrobe, blending comfort with classic beauty.

Price: $52 | Buy on Na-kd

19. Bold Elegance: CHIKO Satara Square Toe Block Heels

The CHIKO Satara Square Toe Block Heels Mary Jane Shoes in a striking red color are the epitome of bold elegance. These shoes feature a glossy patent-leather upper and a comfortable leather lining, perfect for those seeking a blend of style and comfort. The rubber sole ensures durability and stability, making them ideal for long walks in the city. With a heel height of approximately 2 inches (5 cm), these Mary Janes offer a comfortable elevation, suitable for both professional and casual wear. The square toe design adds a modern touch to the classic Mary Jane silhouette, making them a fashionable choice for the contemporary woman. Whether paired with office attire or a casual ensemble, these shoes are a versatile and stylish addition to any wardrobe.

Price: $112 | Buy on Chikoshoes

20. Sleek Sophistication: River Island's Black Block Heel Sandal

The River Island block heel sandal in black stands out as a fashionable and adaptable choice for style-conscious individuals. These sandals, with their matte faux-leather upper, present a refined and chic look suitable for both professional environments and evening outings. The adjustable strap, equipped with a pin-buckle fastening, provides a snug and comfortable fit for a range of foot sizes and shapes. The peep toe design lends an element of femininity and sophistication, making these sandals fitting for a variety of settings, from formal events to more relaxed occasions. The mid block heel offers a modest lift, ensuring ease and comfort during extended periods of urban activities or daily errands. Ideal for enhancing a summer party ensemble or a casual daytime look, these sandals merge practicality with contemporary fashion, making them a valuable addition to any collection.

Price: $30 | Buy on Asos

21. Sleek Elevation: Gleaming Black Leather Platform Ankle Strap Pumps

Crafted from genuine leather, these pumps offer a luxurious and durable quality, perfect for those who appreciate fine materials. The modern Mary Jane silhouette, featuring a squared toe upper and a low-cut collar atop a 1" toe platform, brings a contemporary edge to a timeless design. The adjustable ankle strap with a shiny gold buckle not only adds a touch of sophistication but also ensures a secure and comfortable fit for long city walks. The 3.5" wrapped block heel provides a stylish lift, while the cushioned insole and rubber sole with nonskid markings promise comfort and stability. These pumps are an ideal choice for professional settings or evening events, offering an elegant and polished look without compromising on comfort.

Price: $170 | Buy on Lulus

22. Pearl Perfection: Elegant Square Toe Chunky Heel Pumps

The Elegant Imitation Pearl Metal Square Toe Chunky Heel Back Empty Pumps in Apricot are a blend of classic elegance and modern design. These pumps feature a unique back empty style, coupled with a sophisticated square toe and adorned with delicate imitation pearls and metal embellishments. The adjustable buckle closure ensures a customizable and comfortable fit, suitable for a variety of occasions from daily wear to parties. The chunky heel provides stable and comfortable elevation, ideal for long walks in the city or busy commuting days. These pumps are not just shoes, but a statement of style, combining the practicality of rubber soles and PU lining with the elegance of their unique design. Perfect for the fashion-forward woman, these pumps offer a stylish solution for elevating any outfit with comfort and grace.

Price: $62 | Buy on Stylewe

23. Sleek Sophistication: CHIKO Fatma Stiletto Mary Janes

The CHIKO Fatma Pointy Toe Stiletto Mary Jane Shoes in Beige are a perfect example of sleek sophistication. These shoes feature a luxurious leather upper and lining, offering both durability and a refined look. The pointy toe design and stiletto heel, measuring approximately 2.5 inches (6 cm), combine to create an elegant silhouette that's perfect for both office and evening wear. The rubber sole adds practicality, ensuring stability and comfort during long walks. These Mary Janes are a testament to minimalist elegance, making them a versatile addition to any fashion-conscious woman's wardrobe. Whether you're dressing up for a special occasion or elevating your everyday style, these shoes provide a blend of comfort and chic design.

Price: $106 | Buy on Chikoshoes

24. Pink Perfection: Monki's Diamante Heart Slingback Heels

The Monki slingback pointed toe heels are a stunning blend of fashion and functionality. Their bright pink, glossy satin-style upper injects a vibrant pop of color into any ensemble. Adorned with a diamante heart embellishment, these heels add a touch of glamour and sophistication, ideal for special occasions or to brighten up your daily wardrobe. The elasticated slingback strap and effortless slip-on style offer a snug and convenient fit, perfect for the on-the-move lifestyle. With a mid-point heel, they provide a comfortable lift, well-suited for extended periods of city wear or day-long events, without sacrificing fashion appeal. More than just footwear, these heels act as a statement accessory, enhancing everything from a sleek office look to a playful party outfit.

Price: $39 | Buy on Asos

25. Understated Elegance: CHIKO Jevette Block Heel Mary Janes

The CHIKO Jevette Pointy Toe Block Heels Mary Jane Shoes in Brown are a testament to understated elegance. Crafted with a premium leather upper and lining, these shoes promise both durability and a polished look. The pointy toe design adds a touch of sophistication, while the 1.5-inch (4 cm) block heel offers a comfortable lift, perfect for long walks around the city. The minimalist design of these Mary Janes makes them a versatile choice, easily transitioning from office wear to evening attire. Their rubber sole ensures stability and comfort, making them a practical choice for the modern, style-conscious woman. Whether you're looking for a shoe that combines comfort with a classic style or a versatile addition to your wardrobe, these Mary Jane shoes tick all the boxes.

Price: $118 | Buy on Chikoshoes