Considering your shoes can make or break your look, it is essential to pick the right pair. Having a pair (or two or three) of sleek and timeless derby shoes in your closet can certainly make the decision easier. This style of shoe is ideal for work, your weekend, and every occasion, event, and style choice in between.  Like Oxfords, derbys are a standard yet classic and comfortable dress shoe that is suitable for formal occasions as well as the right casual and smart casual looks. A pair of derbys can look just as good with jeans as they do with a suit. 

  1. Black Source: @byjad via Instagram Source: @yuichiro___ii via Instagram Source: @somiarthreads via Instagram Source: @matureddaddylover via Instagram Source: @calabroshoestore via Instagram Besides low-rise white sneakers, black derbys are one of the most versatile shoes that can take you from work to drinks to dinner to after dinner drinks. Black derbys come in a variety of designs and styles including matte leather, patent leather (Ooh! Shiny!), and suede, to name a few. Wear your patent leather pair with gray trousers and your favorite band t-shirt in black or gray. Try a smart casual look with matte leather derbys, black ankle pants, and a short sleeve printed button-up shirt.
  2. Boots Source: @angelicrussstart via Instagram Source: @martinelliott_ via Instagram Source: @sidewalkstyle_ via Instagram Source: @allissonguima via Instagram Did you know you can also enjoy your derbys in the form of a boot? They appear just like the standard design that you know and love, but with a taller shaft and an open lacing system, giving any outfit a sleek military touch. Keep it casual with distressed jeans and a t-shirt, perhaps throwing on a blazer if you feel that’s the right move. Or, wear dark indigo straight leg jeans with a button-up and two-toned brown and tweed derby boots for a more classic and vintage look.
  3. Brogue Source: @jimlawson_ via Instagram Source: @mrhoc_style_saigon via Instagram Source: @time_for_design via Instagram Source: @lanxshoes via Instagram Source: @normanvilalta via Instagram A brogue is a shoe that features decorative perforations and is available in many different styles of footwear, including derbys. A derby brogue has a bold, yet fashionable appearance and can be dressed up and dressed down. Remember, derby shoes are very versatile. Dress up your daily khakis and polo with chestnut brown derby brogues. Your fellow office husbands and wives will thank you.
  4. Burgundy Source: @rollienation via Instagram Source: @amarast via Instagram Source: @fernando_gent via Instagram Source: @chunkie2.0 via Instagram Source: @urban_sartorialist via Instagram Wearing your derbys in an atypical colorway, such as burgundy, with a standard outfit of jeans and a navy polo or button-up will turn your style game up a notch. Or, wear your burgundy derbys with tailored burgundy suit pants, a white and maroon striped button-up, with a navy blazer and pocket square that brings the whole color palette together. 
  5. Cap Toe Source: @byjad via Instagram Source: @iamrahimbandwala via Instagram Source: @laurenslindeman via Instagram Source: @saurabhmalviya_ via Instagram Source: @top_taws via Instagram This style of derby shoe features an extra piece of leather added to the toe. They can feature broguing around the cap-toe and sometimes a medallion. They tend to be considered more casual than formal, but style rules are meant to be broken. Wearing them with cropped wide-leg pleated pants and a linen short-sleeve shirt keeps you trendy and stylish.
  6. Classic Source: @micelli via Instagram Source: @edwardgreen1890 via Instagram Source: @stylebyblain via Instagram Source: @edwardgreen1890 via Instagram Classic derbys are easy to wear. Opt for sleek, simple styles with minimal stitch detailing. Plain, leather, simple, done.
  7. Dark Brown Source: @dxoxkxkxo via Instagram Source: @fridaraimund via Instagram Source: @gagagagagaga333 via Instagram Source: @estilisman via Instagram Dark brown leather derby shoes are ideal for work and formal events. A brogue-style derby with decorative perforations adds a sense of formality as well. Wear your bespoke chestnut patina leather derby shoes with black trouser socks, light gray suit pants, and a black fitted button-up sans tie. Let your shoes speak for themselves.
  8. Lace Source: @atulsonawane_official via Instagram Source: @bernhardroetzel via Instagram Source: @gu_acamolly via Instagram Source: @nashkeitus via Instagram Source: @triplepape_ via Instagram Selvedge denim, a bomber jacket, and black matte derby shoes laced up make for a nice smart casual look on your next day off. Perhaps you have a formal event on the horizon? Patent lace-up derbys are the perfect way to finish off your tux look. Maybe your next event is slightly less formal? Pair your lace-up derby shoes with skinny tailored ankle pants and a white formal tuxedo shirt, no jacket, no tie, no pocket square, no cuff links; no problem.
  9. Round Toe Source: @iljajah via Instagram Source: @iljajah via Instagram Source: @_johnjarrett via Instagram Source: @sebastyan_row via Instagram The rounded toe is the most traditional and basic shoe shape. They tend to be quite spacious and comfortable, especially if your feet are on the broad or wide side. Since this toe shape is so simple, it can be innocuous, making this style of shoe easy to pull off for pretty much everyone.
  10. Style Source: @mchunut via Instagram Source: @allissonguima via Instagram Source: @julianpiket via Instagram Source: @melikkam via Instagram Using fashion to show off your style is part of the fun of getting dressed. Sure, keeping it simple for certain occasions can be the right move, but being able to wear your newest safari jacket and how it looks great with skinny black jeans, a black Oxford shirt, and your matte black brogue lace-up derby shoes shows off your unique style. Are you jealous of that guy that somehow manages to pair his derby shoes with shorts and a blazer? Don’t be. Just be that guy. An indigo blue short and blazer set with a chambray blue t-shirt and slip-on brown derby shoes is the perfect way to ease into the look.
  11. Suede Source: @livhipp via Instagram Source: @mario_bertulli via Instagram Source: @pshurley007 via Instagram Source: @armandomadrid via Instagram Yes, leather derby shoes are timeless and classic, but a suede pair can offer a more relaxed and contemporary feel, making them the perfect shoe for your favorite casual and smart-casual outfits. They are available in a variety of colorways, including brown, black, navy, white, burgundy, and tan to name a few. There is an option for every man and every event.
  12. Suit Source: @acesiki via Instagram Source: @artworth_brothers via Instagram Source: @alexsmiles1 via Instagram Source: @gentlemenslounge via Instagram Source: @alexsmiles1 via Instagram Derby shoes are the perfect go-to dress shoe for any suit because they can seamlessly work with a wide array of suits from casual to more formal. Dark brown and black leather derby shoes with minimal brogue detailing look best with more formal suiting while casual suits look better with a heavier brogue pattern and suede fabrications.
  13. Vintage Source: @ignoreatyourperil via Instagram Source: @paulevansny via Instagram Source: @rowanrow via Instagram Source: @newyorkersinthecity via Instagram Source: @eremiashoes via Instagram You can either go with an entire vintage look or just vintage derby shoes. The choice is yours (feels good to be in charge, eh?). The more worn-in the leather is, the more vintage your derbys will look.  Conclusion Derby shoes can be dressed up or dressed down, but however, you choose to style them, make sure they fit properly. Wearing an ill-fitting shoe can take away from the stylish look you are trying to put forward. They should fit securely across the arch with no slippage in the heel when walking. The fit across the ball of your foot will soften and stretch over time, so upon purchase, ensure the fit across that area is firm. Also, you do not want your toes to touch the end of the toe-end of your shoe. A thumb-width is ideal but can vary with each style.

See more about - The Top 31 Men’s Going Out Shoe Ideas

Considering your shoes can make or break your look, it is essential to pick the right pair. Having a pair (or two or three) of sleek and timeless derby shoes in your closet can certainly make the decision easier. This style of shoe is ideal for work, your weekend, and every occasion, event, and style choice in between.  Like Oxfords, derbys are a standard yet classic and comfortable dress shoe that is suitable for formal occasions as well as the right casual and smart casual looks. A pair of derbys can look just as good with jeans as they do with a suit. 

  1. Black Source: @byjad via Instagram Source: @yuichiro___ii via Instagram Source: @somiarthreads via Instagram Source: @matureddaddylover via Instagram Source: @calabroshoestore via Instagram Besides low-rise white sneakers, black derbys are one of the most versatile shoes that can take you from work to drinks to dinner to after dinner drinks. Black derbys come in a variety of designs and styles including matte leather, patent leather (Ooh! Shiny!), and suede, to name a few. Wear your patent leather pair with gray trousers and your favorite band t-shirt in black or gray. Try a smart casual look with matte leather derbys, black ankle pants, and a short sleeve printed button-up shirt.
  2. Boots Source: @angelicrussstart via Instagram Source: @martinelliott_ via Instagram Source: @sidewalkstyle_ via Instagram Source: @allissonguima via Instagram Did you know you can also enjoy your derbys in the form of a boot? They appear just like the standard design that you know and love, but with a taller shaft and an open lacing system, giving any outfit a sleek military touch. Keep it casual with distressed jeans and a t-shirt, perhaps throwing on a blazer if you feel that’s the right move. Or, wear dark indigo straight leg jeans with a button-up and two-toned brown and tweed derby boots for a more classic and vintage look.
  3. Brogue Source: @jimlawson_ via Instagram Source: @mrhoc_style_saigon via Instagram Source: @time_for_design via Instagram Source: @lanxshoes via Instagram Source: @normanvilalta via Instagram A brogue is a shoe that features decorative perforations and is available in many different styles of footwear, including derbys. A derby brogue has a bold, yet fashionable appearance and can be dressed up and dressed down. Remember, derby shoes are very versatile. Dress up your daily khakis and polo with chestnut brown derby brogues. Your fellow office husbands and wives will thank you.
  4. Burgundy Source: @rollienation via Instagram Source: @amarast via Instagram Source: @fernando_gent via Instagram Source: @chunkie2.0 via Instagram Source: @urban_sartorialist via Instagram Wearing your derbys in an atypical colorway, such as burgundy, with a standard outfit of jeans and a navy polo or button-up will turn your style game up a notch. Or, wear your burgundy derbys with tailored burgundy suit pants, a white and maroon striped button-up, with a navy blazer and pocket square that brings the whole color palette together. 
  5. Cap Toe Source: @byjad via Instagram Source: @iamrahimbandwala via Instagram Source: @laurenslindeman via Instagram Source: @saurabhmalviya_ via Instagram Source: @top_taws via Instagram This style of derby shoe features an extra piece of leather added to the toe. They can feature broguing around the cap-toe and sometimes a medallion. They tend to be considered more casual than formal, but style rules are meant to be broken. Wearing them with cropped wide-leg pleated pants and a linen short-sleeve shirt keeps you trendy and stylish.
  6. Classic Source: @micelli via Instagram Source: @edwardgreen1890 via Instagram Source: @stylebyblain via Instagram Source: @edwardgreen1890 via Instagram Classic derbys are easy to wear. Opt for sleek, simple styles with minimal stitch detailing. Plain, leather, simple, done.
  7. Dark Brown Source: @dxoxkxkxo via Instagram Source: @fridaraimund via Instagram Source: @gagagagagaga333 via Instagram Source: @estilisman via Instagram Dark brown leather derby shoes are ideal for work and formal events. A brogue-style derby with decorative perforations adds a sense of formality as well. Wear your bespoke chestnut patina leather derby shoes with black trouser socks, light gray suit pants, and a black fitted button-up sans tie. Let your shoes speak for themselves.
  8. Lace Source: @atulsonawane_official via Instagram Source: @bernhardroetzel via Instagram Source: @gu_acamolly via Instagram Source: @nashkeitus via Instagram Source: @triplepape_ via Instagram Selvedge denim, a bomber jacket, and black matte derby shoes laced up make for a nice smart casual look on your next day off. Perhaps you have a formal event on the horizon? Patent lace-up derbys are the perfect way to finish off your tux look. Maybe your next event is slightly less formal? Pair your lace-up derby shoes with skinny tailored ankle pants and a white formal tuxedo shirt, no jacket, no tie, no pocket square, no cuff links; no problem.
  9. Round Toe Source: @iljajah via Instagram Source: @iljajah via Instagram Source: @_johnjarrett via Instagram Source: @sebastyan_row via Instagram The rounded toe is the most traditional and basic shoe shape. They tend to be quite spacious and comfortable, especially if your feet are on the broad or wide side. Since this toe shape is so simple, it can be innocuous, making this style of shoe easy to pull off for pretty much everyone.
  10. Style Source: @mchunut via Instagram Source: @allissonguima via Instagram Source: @julianpiket via Instagram Source: @melikkam via Instagram Using fashion to show off your style is part of the fun of getting dressed. Sure, keeping it simple for certain occasions can be the right move, but being able to wear your newest safari jacket and how it looks great with skinny black jeans, a black Oxford shirt, and your matte black brogue lace-up derby shoes shows off your unique style. Are you jealous of that guy that somehow manages to pair his derby shoes with shorts and a blazer? Don’t be. Just be that guy. An indigo blue short and blazer set with a chambray blue t-shirt and slip-on brown derby shoes is the perfect way to ease into the look.
  11. Suede Source: @livhipp via Instagram Source: @mario_bertulli via Instagram Source: @pshurley007 via Instagram Source: @armandomadrid via Instagram Yes, leather derby shoes are timeless and classic, but a suede pair can offer a more relaxed and contemporary feel, making them the perfect shoe for your favorite casual and smart-casual outfits. They are available in a variety of colorways, including brown, black, navy, white, burgundy, and tan to name a few. There is an option for every man and every event.
  12. Suit Source: @acesiki via Instagram Source: @artworth_brothers via Instagram Source: @alexsmiles1 via Instagram Source: @gentlemenslounge via Instagram Source: @alexsmiles1 via Instagram Derby shoes are the perfect go-to dress shoe for any suit because they can seamlessly work with a wide array of suits from casual to more formal. Dark brown and black leather derby shoes with minimal brogue detailing look best with more formal suiting while casual suits look better with a heavier brogue pattern and suede fabrications.
  13. Vintage Source: @ignoreatyourperil via Instagram Source: @paulevansny via Instagram Source: @rowanrow via Instagram Source: @newyorkersinthecity via Instagram Source: @eremiashoes via Instagram You can either go with an entire vintage look or just vintage derby shoes. The choice is yours (feels good to be in charge, eh?). The more worn-in the leather is, the more vintage your derbys will look.  Conclusion Derby shoes can be dressed up or dressed down, but however, you choose to style them, make sure they fit properly. Wearing an ill-fitting shoe can take away from the stylish look you are trying to put forward. They should fit securely across the arch with no slippage in the heel when walking. The fit across the ball of your foot will soften and stretch over time, so upon purchase, ensure the fit across that area is firm. Also, you do not want your toes to touch the end of the toe-end of your shoe. A thumb-width is ideal but can vary with each style.

See more about - The Top 31 Men’s Going Out Shoe Ideas

Considering your shoes can make or break your look, it is essential to pick the right pair. Having a pair (or two or three) of sleek and timeless derby shoes in your closet can certainly make the decision easier. This style of shoe is ideal for work, your weekend, and every occasion, event, and style choice in between. 

Like Oxfords, derbys are a standard yet classic and comfortable dress shoe that is suitable for formal occasions as well as the right casual and smart casual looks. A pair of derbys can look just as good with jeans as they do with a suit. 

1. Black

Source: @byjad via Instagram

Source: @yuichiro___ii via Instagram

Source: @somiarthreads via Instagram

Source: @matureddaddylover via Instagram

Source: @calabroshoestore via Instagram

Besides low-rise white sneakers, black derbys are one of the most versatile shoes that can take you from work to drinks to dinner to after dinner drinks. Black derbys come in a variety of designs and styles including matte leather, patent leather (Ooh! Shiny!), and suede, to name a few.

Wear your patent leather pair with gray trousers and your favorite band t-shirt in black or gray. Try a smart casual look with matte leather derbys, black ankle pants, and a short sleeve printed button-up shirt.

2. Boots

Source: @angelicrussstart via Instagram

Source: @martinelliott_ via Instagram

Source: @sidewalkstyle_ via Instagram

Source: @allissonguima via Instagram

Did you know you can also enjoy your derbys in the form of a boot? They appear just like the standard design that you know and love, but with a taller shaft and an open lacing system, giving any outfit a sleek military touch. Keep it casual with distressed jeans and a t-shirt, perhaps throwing on a blazer if you feel that’s the right move. Or, wear dark indigo straight leg jeans with a button-up and two-toned brown and tweed derby boots for a more classic and vintage look.

3. Brogue

Source: @jimlawson_ via Instagram

Source: @mrhoc_style_saigon via Instagram

Source: @time_for_design via Instagram

Source: @lanxshoes via Instagram

Source: @normanvilalta via Instagram

A brogue is a shoe that features decorative perforations and is available in many different styles of footwear, including derbys. A derby brogue has a bold, yet fashionable appearance and can be dressed up and dressed down. Remember, derby shoes are very versatile. Dress up your daily khakis and polo with chestnut brown derby brogues. Your fellow office husbands and wives will thank you.

4. Burgundy

Source: @rollienation via Instagram

Source: @amarast via Instagram

Source: @fernando_gent via Instagram

Source: @chunkie2.0 via Instagram

Source: @urban_sartorialist via Instagram

Wearing your derbys in an atypical colorway, such as burgundy, with a standard outfit of jeans and a navy polo or button-up will turn your style game up a notch. Or, wear your burgundy derbys with tailored burgundy suit pants, a white and maroon striped button-up, with a navy blazer and pocket square that brings the whole color palette together. 

5. Cap Toe

Source: @iamrahimbandwala via Instagram

Source: @laurenslindeman via Instagram

Source: @saurabhmalviya_ via Instagram

Source: @top_taws via Instagram

This style of derby shoe features an extra piece of leather added to the toe. They can feature broguing around the cap-toe and sometimes a medallion. They tend to be considered more casual than formal, but style rules are meant to be broken. Wearing them with cropped wide-leg pleated pants and a linen short-sleeve shirt keeps you trendy and stylish.

6. Classic

Source: @micelli via Instagram

Source: @edwardgreen1890 via Instagram

Source: @stylebyblain via Instagram

Classic derbys are easy to wear. Opt for sleek, simple styles with minimal stitch detailing. Plain, leather, simple, done.

7. Dark Brown

Source: @dxoxkxkxo via Instagram

Source: @fridaraimund via Instagram

Source: @gagagagagaga333 via Instagram

Source: @estilisman via Instagram

Dark brown leather derby shoes are ideal for work and formal events. A brogue-style derby with decorative perforations adds a sense of formality as well. Wear your bespoke chestnut patina leather derby shoes with black trouser socks, light gray suit pants, and a black fitted button-up sans tie. Let your shoes speak for themselves.

8. Lace

Source: @atulsonawane_official via Instagram

Source: @bernhardroetzel via Instagram

Source: @gu_acamolly via Instagram

Source: @nashkeitus via Instagram

Source: @triplepape_ via Instagram

Selvedge denim, a bomber jacket, and black matte derby shoes laced up make for a nice smart casual look on your next day off. Perhaps you have a formal event on the horizon? Patent lace-up derbys are the perfect way to finish off your tux look. Maybe your next event is slightly less formal? Pair your lace-up derby shoes with skinny tailored ankle pants and a white formal tuxedo shirt, no jacket, no tie, no pocket square, no cuff links; no problem.

9. Round Toe

Source: @iljajah via Instagram

Source: @_johnjarrett via Instagram

Source: @sebastyan_row via Instagram

The rounded toe is the most traditional and basic shoe shape. They tend to be quite spacious and comfortable, especially if your feet are on the broad or wide side. Since this toe shape is so simple, it can be innocuous, making this style of shoe easy to pull off for pretty much everyone.

10. Style

Source: @mchunut via Instagram

Source: @julianpiket via Instagram

Source: @melikkam via Instagram

Using fashion to show off your style is part of the fun of getting dressed. Sure, keeping it simple for certain occasions can be the right move, but being able to wear your newest safari jacket and how it looks great with skinny black jeans, a black Oxford shirt, and your matte black brogue lace-up derby shoes shows off your unique style.

Are you jealous of that guy that somehow manages to pair his derby shoes with shorts and a blazer? Don’t be. Just be that guy. An indigo blue short and blazer set with a chambray blue t-shirt and slip-on brown derby shoes is the perfect way to ease into the look.

11. Suede

Source: @livhipp via Instagram

Source: @mario_bertulli via Instagram

Source: @pshurley007 via Instagram

Source: @armandomadrid via Instagram

Yes, leather derby shoes are timeless and classic, but a suede pair can offer a more relaxed and contemporary feel, making them the perfect shoe for your favorite casual and smart-casual outfits. They are available in a variety of colorways, including brown, black, navy, white, burgundy, and tan to name a few. There is an option for every man and every event.

12. Suit

Source: @acesiki via Instagram

Source: @artworth_brothers via Instagram

Source: @alexsmiles1 via Instagram

Source: @gentlemenslounge via Instagram

Derby shoes are the perfect go-to dress shoe for any suit because they can seamlessly work with a wide array of suits from casual to more formal. Dark brown and black leather derby shoes with minimal brogue detailing look best with more formal suiting while casual suits look better with a heavier brogue pattern and suede fabrications.

13. Vintage

Source: @ignoreatyourperil via Instagram

Source: @paulevansny via Instagram

Source: @rowanrow via Instagram

Source: @newyorkersinthecity via Instagram

Source: @eremiashoes via Instagram

You can either go with an entire vintage look or just vintage derby shoes. The choice is yours (feels good to be in charge, eh?). The more worn-in the leather is, the more vintage your derbys will look. 

Conclusion

Derby shoes can be dressed up or dressed down, but however, you choose to style them, make sure they fit properly. Wearing an ill-fitting shoe can take away from the stylish look you are trying to put forward.

They should fit securely across the arch with no slippage in the heel when walking. The fit across the ball of your foot will soften and stretch over time, so upon purchase, ensure the fit across that area is firm. Also, you do not want your toes to touch the end of the toe-end of your shoe. A thumb-width is ideal but can vary with each style.

See more about - The Top 31 Men’s Going Out Shoe Ideas

See more about - The Top 31 Men’s Going Out Shoe Ideas