What To Wear With Dress Shoes Men

Dress shoes differ in style, but they all have formal style because they’re matched with formal trends. For example, we have oxford dress shoes, boot dress shoes, penny loafer dress shoes, slip-on dress shoes, strap slip-on dress shoes and so much more.

Black and brown are the most popular colors when it comes to dress shoes. Brown shoes can match with gray trousers, navy blue suits and pants, and black formal trends, yet black shoes will match with almost every trend. So it is better you own both brown and black dress shoes.


What To Wear With Dress Shoes Men

What To Wear With Dress Shoes Men



Always remember to complement your shoes with a matching belt, do not wear black shoes with a brown belt.


Today on Olixe, I have compiled a list of the best dress shoes every man should own, I know you have your own taste for shoes, but you won’t fail to find a shoe that fits your desires.

NOTE: Links to stores where you can buy these Dress shoes for men are listed at the end of this post.




  1. 1. Windsor’ Wingtip Oxford (Men)

Dress Shoes 1


  • Bostonian Men’s Pavillion Oxford – $34.51
  • Florsheim Men’s Bastille Bit Loafer – $99.95
  • Johnston & Murphy Men’s Melton Oxford – $96.82
  • Cole Haan Men’s Air Madison Wing Oxford – $127.99
  • Giorgio Brutini Men’s 66014 Boot – $43.77

This cognac oxford dress shoe has scored number one on the list of top ten dress shoes for men. Let’s see what makes this Windsor’ Wingtip Oxford shoe different from most dress shoes. The cognac color unique and stylish, the shoe features a pure leather upper, leather lining and leather sole which guarantee durability; it also has a brogue trim which makes the shoe stand out.

What to wear with this Cognac Oxford Dress Shoe for men?

Tip 1: Navy blue suit will match with this shoe, to look smart, you can wear a slim fit navy blue suit and a white shirt, and then complement the shoes with a cognac leather belt. If you want to look formal but casual at the same time, you can leave the last three buttons of your dress shirt open; make sure the collar of your shirt is stiff so that it stands out from the suit. For those going to business meetings of work, you might need to look formal, so a slim navy blue tie will be a great match.

Tip 2: You can also wear these shoes with a black / gray trouser. These two colors match with Cognac brown shoes. If you don’t want to wear a blazer, then complement your trend with black / pink / white or yellow dress shirt.

  1. 2.

    Bostonian Men’s Evanston Slip-on

Dress Shoes 7

If you want to buy your father or husband a gift, i suggest you surprise them with these old school slip-on shoes. These Evanston Slip-on shoes have been on fashion since 1990’s and they still rock. They feature leather upper, leather sole which makes them durable and trendy. Let your dad or husband hit the office with these classic dress shoes.

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What to wear with this Bostonian’s Evanston slip-on dress shoe?

Tip 1: Any color of formal trouser will match with these Evanston slip-on shoes. If you want to look simple but smart, try to complement the trend with a classic cufflink shirt and a black leather belt.

Tip 2: You can also wear them with formal khaki pants or chinos. To look stylish, you can wear a pink / blue dress shirt with your khaki pants, and then complement the trend with a black blazer.

  1. 3.

    Brownlie’ Wingtip Oxford

Dress Shoes 4

Cognac dress shoes have almost the same way of styling, the only difference we have between shoe (1) and Shoes (4) is that shoe (1) is a bit lighter and its brogue style is quite different from shoe (4). This Brownlie’ Wingtip Oxford shoe features leather upper, synthetic leather lining and a rubber sole.

When it comes to complementing these shoes with other fashion trend, you can wear them way as the ones in position (1)

However, with this type of dress shoe, you can match it with a straight leg denim jean. To add value to this trend, you can wear a pink or white striped dress shirt and a black blazer.

  1. 4. Shipley’ Chelsea Boot

Dress Shoes 5

You can wear dress boots to work or any business meeting. Dress boots are always expensive because they look more elegant than normal dress shoes. So due to their high price very few men wear them as dress shoes. This is a trendy Chelsea boot which features leather upper. leather lining , and a rubber sole. The boot is elastic on the sides, so it is very easy to wear them.

What to wear with these Chelsea Dress Boots?

Tip 1: Wear this Chelsea dress boot with a suit to work, this is a formal fashion trend. Make sure you complement the boots with a black slim leather belt. In this case, all colors of suits will match with this boot. If you don’t want to wear a suit to work, then team them with a formal trouser and a classy dress shirt.


  1. 5.

    Cole Haan Air Adams Split Oxford

Dress Shoe 3

Coole Haan makes the best dress shoes at an affordable price, you can grab this cool split oxford tan brown shoe for as low as $139. I found this great shoe on Zappos and i think it is worth, it features burnished upper leather, leather lining a rubber sole and a cushioned NIKE AIR technology which makes them comfortable on the inside.

Styling this Cole Haan Air Adams Split Oxford:

Tip 1:- Team this tan brown dress shoe with a gray trouser. To add value to your style, you should complement the shoe with a tan brown crafted leather belt, and then wear a blue, pink, white, black dress shirt.

Tip 2:- You can also wear them with formal straight leg denim jeans. Most men love wearing jeans to work, so this dress shoe will match with formal jeans. Complement the trend with a classic long sleeved check shirt.

  1. 6.

    Caesy’ Cap Toe Oxford

Dress Shoe 6

I love brogues and i like the idea of integrating brogue style with an oxford dress shoe. This trendy cap toe dress shoe will match most formal trends, it is the type of shoe you can wear to office, business meeting, job interview, party and so much more. It features lace-up style, leather upper, leather lining and leather sole. Designed by my favorite designer ”Salvatore Ferragamo”,

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What to wear with Caesy’ Cap Toe Oxford Dress Shoe?

Tip1:- You can team this shoe with a slim-fit suit. In this case, you can match it with a gray suit, black suit and navy blue suit. Make sure you complement it with a brandy leather belt. If you wear a navy blue or black suit with this shoe, you might need to wear a bright colored shirt because the shoes are dark, so i suggest a pink or white cufflink dress shirt will match with your outfit, let the tie be slim and dark colored.

Tip 2:- Not every one wears a suit to work, so chino and khaki lovers, this is a great dress shoe for you. Make sure that your khaki pants have no pleats on the front; flat pants will also look good with this Cap Toe Oxford Dress Shoe. If you want to match it with jeans, that will be okay, but the jeans have to be formal or with a very simple fade.

  1. 7.

    Air Madison’ Oxford

Dress Shoes 9

I’m not obsessed with tan brown dress shoes, this shoe just grabbed my attention while on Nordstrom and it was among the top most liked dress shoes. It features upper leather, leather and rubber sole which makes the shoes durable. It is both formal and casual, so the options of matching it with other fashion trends are limitless.

What should you wear with this Air Madison’ Oxford Dress Shoe?

Tip 1: You can team it with a cream straight leg fitting jean, then complement your jeans with a stripped / check shirt, make sure the shirt has some cream prints to match with the cream jeans, or you wear a dark colors like black, navy blue and dark gray. For those who love suspenders, you can leave out the belt and opt for brown leather suspenders.

Tip 2: Fashionable guys, you can team this British tan oxford dress shoe with a dirty brown slim fit jean. To look stylish, you can fold the bottom of the jeans, then match the brown jeans an off grey long sleeved shirt, then complement the shirt with a black buscoat and a slim white/grey striped ties, fold the sleeves of the shirt.


  1. 8.

    Marco’ Monk Strap Loafer

Dress Shoes 10

This is a catalux grey dress shoe, this is the kind of shoe you can match with a suit or trouser and look smart. Catalux grey is dark so you need to match this shoe with bright colors. This Marco’ Monk Strap Loafer features leather upper, leather lining and a leather sole. The buckle closure makes it easy to wear, some time i don’t like lace-up shoes because they take to much time.

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So, let’s see what you can wear with this Catalux grey loafer

Tip 1:- My best choice is a grey suit. To look fashionable, opt for a slim fit grey suit, a two button style will look good, and then match it with a white/purple/pink striped shirt. The three colors in the shirt match with grey, so you can complement the shirt with a check slim tie which has purple/pink and grey prints.

  1. 9.

    Rockport Office Essentials Ellingwood

Dress Shoe 2

This is an ordinary dress shoe anyone can afford, the shoe costs only $100 yet it looks awesome, i just landed on this black Rockport Office shoe on ZAPPOS, the shoe has got over 234 reviews, which means many people have purchased the shoe, this makes it popular and it scores position (9) on TopTenShoes. You can easily style this shoe; it matches with suits, jeans, khaki or chino pants and formal trousers.

This Rockport office dress shoe features a waterproof leather upper which will keep your feet dry, a padded tongue and a cushioned collar to provide extra comfort. It is not heavy, because of its polyurethane outsole.

  1. 10.

    Langley’ Double Monk Strap Slip-On

Dress Shoes 6

Double monk strap slip-on dress shoes are not very common, most of them don’t look nice but his Langley ‘dark tan shoe looks cool. You can match this monk strap dress shoe with most formal trends. The shoe features warm burnished leather upper and a sleek design. It also has leather sole which makes the shoe durable and trendy. You can ware this shoe with a suit and a formal trouser.

Judging from its style, I’m not so sure if it will match with formal jeans and chinos, but with fashion, you can try it out and see it matches.



  • Shoe type 1:- bit.ly/11Y6Y5N
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  • Shoe type 3:- bit.ly/1bzoYJo
  • Shoe type 4:- bit.ly/12puW01
  • Shoe type 5:- bit.ly/jWepXQ
  • Shoe type 6:- bit.ly/1bzpaZc
  • Shoe type 7:- bit.ly/12IxAiR
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  • Shoe type 9:- bit.ly/175msy1
  • Shoe type 10:- bit.ly/1a7sKvC


Dress shoes are formal in style; you can wear them to work or any formal event. As you have seen above, these shoes differ in type; we have oxfords, loafers, Chelsea boots and slip-on dress shoes. It is not a must that you have to team them with suits, not every job or career requires you to wear suits, so you can wear them with jeans just the guy in the picture above. Unlike penny loafers, you will need to wear socks with these dress shoes.

Feel free to ask a question or leave your comments and thoughts below…

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