How to Combine Shoes & Boots with Business Suits – Gentlemen’s Outfit Ideas

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If you wear a suit to work every day for important meetings, sometimes it may seem that all the shoes you see are black or brown oxfords. Fear not, though, as there are many more opportunities for creativity here, which we’ll discuss today.

Changes in office dress codes across the globe have actually enabled men to wear a much broader range of shoes and boots to the office. Switching up your footwear can really create an interesting and fresh take on your regular suit, especially if you also change up a few accessories.

Dan Trepanier - Brown business suit
Dan Trepanier – Brown business suit

General Tips To Combine Business Suits & Footwear

In general, business attire is a rather formal dress code; as such, you’ll need formal shoes. That means your shoes or boots should be all leather with leather soles. You absolutely don’t want to wear any trainers or sneakers with a business suit, nor modern kinds of oxford-sneaker combinations with thick rubber soles. Also, chunky, thick double- or triple-leather soles are not appropriate for all business suits, and neither are chunky rubber soles. It goes without saying that you should avoid any kind of contrasting materials, such as spectators either in leather fabric or maybe even cowhide.

Black "dress shoes" with blue soles
Black “dress shoes” with blue soles – definitely avoid these kinds of shoes

In terms of the last, you want something that is classic and elongated, maybe with a rounded toe or a chisel toe but definitely no chunky square-looking toe boxes. In terms of colors and finishes, a classic box calf in black or other darker colors, such as oxblood or chocolate brown are your best bet. Avoid any crocodile or stingray leather, or something like elephant, because they’re too exotic. Maybe you can pull them off if you’re the boss. If you’re not, it’s not the best option.

If your office is a bit more relaxed and you want to add a dash of color, maybe consider adding a pair of shoelaces in a different color, because that really changes the look of your entire shoe combination. Generally, a shoe paired with formal business attire should cover the entire foot, which means no loafers with a deep cut, for example, and when you wear a double-breasted suit, skip loafers altogether because they’re too informal.

FRED AND MATT overshoes in Black
A pair of protective overshoes, from Swedish brand Fred&Matt

If you live in a cold climate and you have a lot of snow in the winter, avoid wearing your really nice dress shoes directly to the office–maybe have them at the office, or cover them up with rubber protectors. Alternatively, a pair of lined winter boots that keep your feet toasty warm while heading to the office could work, after which you’d switch into your nice dress shoes.

What Are the Footwear Options for Business Suits?

It all starts with the oxford, of course, and derbies. It doesn’t matter if it’s a cap-toe, a semi-brogue, quarter-brogue, full brogue, or a wholecut. These days, single- and double-monk strap shoes are also very office appropriate.

In terms of boots, Chelsea boots, Balmoral boots, Jodhpur boots, and even button boots are all office appropriate.

Footwear Styles & Colors

Black Oxfords with navy trousers (Pictured: Navy and Yellow Shadow Stripe Ribbed Socks from Fort Belvedere)
Black Oxfords with navy trousers (Pictured: Navy and Yellow Shadow Stripe Ribbed Socks from Fort Belvedere)

If you can just afford one pair of business dress shoes or boots, it should always be black. It’s the standard for business attire. Still, when you put together a combination of footwear and a suit, you always want to opt for some element of contrast. If you have a black suit, maybe have a pair of gray striped socks with your black shoes, would be a good choice.

On the other hand, if you have a navy, dark blue, medium gray, or charcoal suit, the black shoe would provide enough of a contrast that you can just get socks that are matching to the pants or that picks up the color of an accessory, your shirt, your pocket square, or your tie. If for some reason, you’re not a big fan of black, you can go with a dark chocolate brown (sometimes in Italian, it’s called testa di moro), or a few shades lighter. Nothing bright red or light tan, though!

Superbly polished burgundy oxblood double monks by Butler
Superbly polished burgundy oxblood double monks by Butler

Personally, my favorite shoe and boot color for business suits is oxblood. Why? Because it’s different than the typical black shoe, dark enough to be taken seriously, and it provides enough contrast to always be visible and visually interesting. As a general rule, a pair of dress shoes will always be a little more formal than a pair of boots when combined with a business suit. Of course, there are exceptions to the rule.

For example, black Balmoral boots sometimes come with a suede insert in the same color, and formality-wise, they’re about as formal as a pair of cap-toe oxfords. They look really great with a stroller ensemble (which isn’t technically a suit, because it’s a black jacket with striped pants), a traditional staple in formal office wear. The other option for a stroller or anyone who loves vintage is a button boot. Oftentimes, they come in contrasting leathers such as black and white, and while they’re a little more flashy, they’re traditionally considered to be office-appropriate.

Dark brown Chelsea boots with with glen plaid trousers (Pictured: Light Brown and Blue Shadow Stripe Ribbed Socks from Fort Belvedere)
Dark brown Chelsea boots with with glen plaid trousers (Pictured: Light Brown and Blue Shadow Stripe Ribbed Socks from Fort Belvedere)

A dark brown Chelsea boot with a blue elastic insert will always make your suit more casual and less formal. If that’s too flashy for you, consider a chocolate-colored suede Chelsea boot, because it has a rougher texture which makes it a bit more casual. In general, in today’s office environments, it’s totally acceptable to wear, and it just adds a bit more character and individuality to your outfit. One way not to pay attention to yourself at the office is to avoid crazy socks.

Pairing Business Suits with Various Shoes and Boots

*Note: be sure to watch the corresponding video to get a complete sense of all the outfits featured here!*

This pair of black oxfords will work well with a Navy Single Breasted Suit (Pictured: Shadow Stripe Ribbed Socks Dark Navy Blue and Royal Blue from Fort Belvedere)
This pair of black oxfords will work well with a Navy Single Breasted Suit (Pictured: Shadow Stripe Ribbed Socks Dark Navy Blue and Royal Blue from Fort Belvedere)

Navy Single-Breasted Suit

Here’s an example for a classic business suit with notched lapels and flat pockets, paired with a classic business tie like a red Prince of Wales check tie, silver cuff links with a monkey fist knot by Fort Belvedere, and black oxfords. In this pair of shoes, I opted for a bit of broguing on the cap toe, which makes it a “quarter brogue.” To add a bit of contrast between the dark navy suit and my black shoes, I went with navy blue shadow striped socks from Fort Belvedere.

If you want it to be even less formal, switch out the white linen pocket square for something printed in silk, get a bolder tie, and maybe switch up the oxfords to a black pair of double monk strap shoes. Of course, a navy two-piece suit with different colored vests can make all the difference, even though the rest of the accessories, including the shoes, remain the same. 

Olive green shoes with navy trousers (Pictured: Navy and Yellow Shadow Stripe Ribbed Socks from Fort Belvedere)
Olive green shoes with navy trousers (Pictured: Navy and Yellow Shadow Stripe Ribbed Socks from Fort Belvedere)

Lighter Navy Blue Suit

If a dark navy suit is too formal for you, the next notch up would be a slightly lighter blue suit, which could be a dark blue or a very light shade of navy. A nice dark blue suit that’s double-breasted with peak lapels is great with a Winchester shirt. A small boutonniere would lighten things up, but you can always skip it in a business context. Olive green shoes would be novel but conservative, and harmonious socks would finish the look.

Wingtip monk strap shoes (Pictured: Shadow Stripe Ribbed Socks Dark Navy Blue and Royal Blue from Fort Belvedere)
Wingtip monk strap shoes (Pictured: Shadow Stripe Ribbed Socks Dark Navy Blue and Royal Blue from Fort Belvedere)

Instead of going lighter with your suit shade, you could also add a subtle pattern, such as a faint windowpane, which relaxes the suit and the overall look. For this outfit, I chose a brownish-red, full-brogue monk strap from Crockett & Jones as a combination, but I could have also worn something in a more oxblood shade, which would have worked maybe even better than this pair. Regardless of what shoes you choose, the shadow striped socks again work well, because they pick up the color of the suit.

Solid & Patterned Gray Suits

Half-brogue black Oxford (Pictured: Shadow Stripe Ribbed Socks Burgundy and light grey from Fort Belvedere)
Half-brogue black Oxford (Pictured: Shadow Stripe Ribbed Socks Burgundy and light grey from Fort Belvedere)

This suit has a subtle undertone of brown, with a very faint reddish stripe. Because of that, it is a little less formal than a solid gray suit, but it’s still considered a business suit, especially since it is a three-piece suit with a double-breasted vest. When combined with a white shirt, white linen pocket square and a small dotted red tie, it is a quintessential business outfit. Here I went with a half-brogue black oxford. You can only see the burgundy and off-white shadow striped socks that pick up the color of the tie if you lift up the pant leg, otherwise, it’s just a very harmonious business combination without any pop of color.

With the same suit, you could also try adding a blue tie with reddish tones and the same pair of reddish brown monk strap shoes from Crockett & Jones shown above; this would make the look a little more casual. Another smart footwear choice would be something like chocolate brown long-wing derbies from Allen Edmonds.

Charcoal Brown Business Suit

Charcoal Brown Business Suit paired with patina monk strap shoes
Charcoal Brown Business Suit paired with patina monk strap shoes
Battleship Gray Jacquard Woven Bow Tie with Printed Light Blue and White Diamonds

Fort Belvedere

Battleship Gray Jacquard Woven Bow Tie with Printed Light Blue and White Diamonds

A photo of a Pocket Square with Monogram Initial Classic White Irish Linen

Fort Belvedere

White Initial Pocket Square – Hand-Embroidered in Italy

Charcoal brown, in my opinion, is a very underrated business color. It’s fantastic because it’s dark, just like a dark gray, yet the brown adds a certain element of warmth to it that is perfectly suited for today’s business environments. Here, I’m wearing it as a true three-piece suit with a double-breasted waistcoat, white shirt, and a gray and blue bow tie. The monk strap shoes I’m pairing it with have a beautiful brown patina, and they just provide enough contrast to the suit so they’re noticeable as shoes.

Charcoal Brown Business Suit with tan monk straps - a more relaxed vibe
Charcoal Brown Business Suit with tan monk straps – a more relaxed vibe
Shantung Striped Green, Purple and Cream Silk Tie - Fort Belvedere

Fort Belvedere

Shantung Striped Green, Purple and Cream Silk Tie

Silk Pocket Square in Brown with Blue, Green, Red Large Paisley Pattern

Fort Belvedere

Silk Pocket Square in Brown with Blue, Green, Red Large Paisley Pattern

Taking the same suit and switching up the accessories creates a very different look. If we switch the white shirt for a light blue shirt, the bow tie for a shantung silk tie in green, white, and purple, and add a purple and green madder silk pocket square, the look is a lot more casual and relaxed. Add an even more contrasting pair of tan monk strap shoes to the mix, and it almost looks like an entirely different suit. If that’s too much for you, you could go with more of a medium tan, which is still contrasting but less in-your-face.

Striped Navy Suit

This is the quintessential power suit and has remained a staple in business or office wardrobes. For a formal outfit, of course, you want to wear it with a white pocket square and a white dress shirt with French cuffs. If you pair it with a contrasting tie, such as a yellow one with a herringbone pattern from Hermes and maybe a pair of navy socks with yellow stripes that pick up the yellow of the tie, and black oxford shoes with a bit of broguing, you have a very classic business outfit.

Striped navy suits are best paired with black oxfords (Pictured: Navy and Yellow Shadow Stripe Ribbed Socks from Fort Belvedere)
Striped navy suits are best paired with black oxfords (Pictured: Navy and Yellow Shadow Stripe Ribbed Socks from Fort Belvedere)

For a personal note, you can add a little boutonniere, but that may not be appropriate for all workplaces. Whether the shoes are cap-toes, half brogues, or full brogues, doesn’t really matter as long as the color is black. If you want to dress down the suit even more, try something like a chartreuse colored knit tie and a purple boutonniere. Remember that the addition of unusual colors into an outfit definitely makes it more casual. Or alternatively, you could wear that same suit with a brownish printed tie, a burgundy polka-dotted pocket square, and reddish-brown monk strap shoes.

Dark Charcoal Flannel Suit

Whether it’s single-breasted or double-breasted, the dark charcoal flannel suit is a staple for business wear. Paired with a red madder silk tie from Fort Belvedere, cuff links, and black oxfords, it is a very formal business outfit, particularly in the winter months, because the flannel texture is a bit more casual than a worsted. If you want to add a dash of color to an otherwise very conservative outfit, always consider your socks.

Suede Chelsea boots paired with a flannel suit
Suede Chelsea boots paired with a flannel suit

If you wanted to take that same suit and make it a bit more casual, keep the white shirt and the white pocket square but add a two-tone white and brown knit tie, as well as brown chocolate-colored suede Chelsea boots that are not as high. Just like flannel, suede is a more casual texture, and because of that, those two work really well together. So if you have a flannel suit in a dark gray or a medium gray, always consider pairing it with either lighter medium or darker brown suede shoes or boots. It will always look the part.

Brown Herringbone Suit

In this example, my suit has a mohair color and burgundy tones which work well with the rest of the outfit. I’ve chosen to pair it with a blue tweed vest and double-soled tan boots from Trickers to create a very unique outfit in blue and brown.

Tan double soled boots from Trickers worn with brown herringbone suit
Tan double soled boots from Trickers worn with brown herringbone suit

Medium Gray Windowpane Suit

Another cool suit for casual offices would be this medium gray flannel suit with a bold white or off-white windowpane. Because it’s such a bold suit pattern, you have to tone down the rest of your outfits and boots. Here, that means white shirt, white pocket square, and solid tie, paired with a pair of black balmoral boots with a black suede insert.

Gray windowpane suit with black balmoral boots
Gray windowpane suit with black balmoral boots

Note that I exchanged the laces with Fort Belvedere shoelaces in gray that pick up the color of the suit to provide some contrast and tie everything together.

Gray Donegal Suit

This ensemble consists of a light blue shirt, the same blue tweed vest, and a mottled pink silk knit tie from Fort Belvedere. Together with a burgundy and blue silk-wool pocket square and blue suede boots, it’s just a very unusual outfit that stands out from the rest of the crowd. If you are just starting out, I think blue suede boots are over-the-top, but if you’re like me and you already have all the basics covered, experimenting with different colors and textures can be a lot of fun.

Blue suede boots paired with a Donegal tweed suit
Blue suede boots paired with a Donegal tweed suit

Brown Houndstooth Suit

Last but not least, one of my favorite casual suit looks, for example, for casual Fridays in the winter, is this suit which is a houndstooth of brown and off-white. I’m pairing it with a turtleneck sweater in a medium brown that provides enough contrast. In combination with mid-brown suede chukka boots, you get a nice blend of earthy tones that is casual and relaxed yet more formal than a regular dress shirt with Chino slacks. 

Mid brown suede chukka boots with a houndstooth suit
Mid brown suede chukka boots with a houndstooth suit

Outfit Rundown

I am wearing a very traditional business suit paired with slightly more casual bigger houndstooth bourette silk tie. I am pairing it with a white shirt, a white pocket square with red cross stitching that picks up the colors of my red tie.

Raphael in a traditional business suit
Raphael in a traditional business suit
Houndstooth Bourette Silk Tie in Burgundy Red Cream - Fort Belvedere

Fort Belvedere

Houndstooth Bourette Silk Tie in Burgundy Red Cream

White Linen Pocket Square with Burgundy Red Handrolled X Stitch

Fort Belvedere

White Linen Pocket Square with Burgundy Red Handrolled X Stitch

Monkey Fist Knot Cufflinks - 925 Sterling Silver Rose Gold Plated

Fort Belvedere

Monkey Fist Knot Cufflinks – 925 Sterling Silver Rose Gold Plated

Shadow Stripe Ribbed Socks Light Grey and Light Blue Fil d'Ecosse Cotton

Fort Belvedere

Shadow Stripe Ribbed Socks Light Grey and Light Blue Fil d'Ecosse Cotton

Charcoal Grey Shoelaces Round - Waxed Cotton Dress Shoe Laces Luxury

Fort Belvedere

Charcoal Grey Shoelaces Round – Waxed Cotton Dress Shoe Laces Luxury

I have classic black shoes; I opted for the black Balmoral boot with a suede insert, and contrasting gray shoe laces that pick up the gray tones of my light gray and light blue socks. My cufflinks are rose gold monkey fist ones from Fort Belvedere that match the rose gold of my pinky ring.

How do you select footwear to pair with your suits? Share with us in the comments!

Reader Comments

  1. To keep it simple, just wear oxblood/burgundy shoes. They go with everything execept brown and black suits (which should not be worn anyway).

  2. Please change the title to make clear that you are now running a silly style magazine instead of a Gentlemans Gazette

  3. Thank you for an interesting if not exhaustive treatise on stylistic possibilities which makes a good attempt to cater for the differences between workplaces in contemporary culture. The conservative (take note Vincenzo) as well as more creative and relaxed approaches are presented for reflection.
    My everyday work shoes are Allen Edmonds cordovan wingtip blucher brogues which are pleasantly versatile and stand up well to the demands of orthopaedic practice.
    On a personal note to Mr Schneider, you have impeccable taste in quality of material but the double-breasted waistcoat with the charcoal brown suit makes you look as if you have “a spare tyre” (excessive abdominal adipose tissue) in the photo. Keep up the good work GG and all the best for 2020.

  4. Great selection you have here Raphael. I personally like the blue suede boots. Would match well with my husband’s style and his suits.

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