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Dress Shoe Options

iamelectroman

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I'm looking to start building out my shoe collection. I wear a suit for work, and as such already have a decent rotation of various black and brown cap-toe oxford dress shoes. My office tends to be smart casual on Fridays, so I want to pick up a couple of more interesting brown dress shoes (loafers, monk straps, chukkas? etc.) to wear with odd trousers and blazers. I would also be wearing these on evenings and weekends whenever I go to a nicer restaurant or the like. I'm looking to probably eventually pick up 2-3 pairs. What would you say would be my best options?
 

Ben W

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Have you considered oxblood in addition to brown? It is very versatile and if you already have a number of browns may be a good option. I'd suggest looking at some double monk straps and maybe some chelsea boots for what you are describing.
 

ValidusLA

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Brown or chili double monk straps.
I also second oxblood. Love oxblood.
 

J.Odelius

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I third oxblood. It can really enrich an outfit and goes with most darker colours!
 

iamelectroman

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Have you considered oxblood in addition to brown? It is very versatile and if you already have a number of browns may be a good option. I'd suggest looking at some double monk straps and maybe some chelsea boots for what you are describing.
I haven't really considered an oxblood, what types of shoes would be best as an oxblood? I also live in a city with hot summers and cold winters, would a chelsea boot be appropriate for spring/summer? Or is it more of a fall/winter only option?
 

Anachronist

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There’s virtually no shoe style that won’t look good in oxblood or burgundy... even flip flops ;-)

Joke aside, I would also support the above mentioned double monks or generally a nice single monk shoe. Alternatively, a split-toe Norwegian or a nice (penny or tassel) loafer are a good smart casual shoe. The Chelseas are probably a better option for fall, winter and the colder spring day, but not first choice for summer. Chukkas are clearly the most casual in the selection you proposed and probably better suited to be paired with denim or chinos rather than worsted/woolen slacks and a more rugged sports coat (Tweed, Hop Sack or Linen).

I have a soft spot for saddle shoes ever since I saw a picture of nifty looking Fred Astaire wearing a pair with grey flannel trousers and a navy blazer, but admit I‘ve not found any yet that really look good. Apart from that, they fall into the more classic (read „old school“) category like spectators (which I love to wear for smart casual) that take a bit of guts to pull off these days because they are eye catching.
 

breakaway01

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dark brown suede chukkas are very versatile and would be my first recommendation.

if you only have captoes then maybe a longwing brogue

agree with a Norwegian split toe -- I am partial to scotchgrain leather
 

Ben W

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I haven't really considered an oxblood, what types of shoes would be best as an oxblood? I also live in a city with hot summers and cold winters, would a chelsea boot be appropriate for spring/summer? Or is it more of a fall/winter only option?
I would say oxblood is even more versatile than black because it can be worn both on casual shoes as well as shoes that are more business (something you'd wear with a suit and tie), whereas black is not typically a great choice for casual. The only place I probably wouldn't do oxblood is with actual formalwear, but I also wouldn't wear brown with that. Anything you'd consider having made in brown I'd say you could consider in oxblood or burgundy instead.

I wear chelsea boots year-round, and with everything from denim up to a dark colored suit, but maybe that is a little bolder than average. I'm a boot guy. 🤷🏻‍♂️
 

iamelectroman

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There’s virtually no shoe style that won’t look good in oxblood or burgundy... even flip flops ;-)

Joke aside, I would also support the above mentioned double monks or generally a nice single monk shoe. Alternatively, a split-toe Norwegian or a nice (penny or tassel) loafer are a good smart casual shoe. The Chelseas are probably a better option for fall, winter and the colder spring day, but not first choice for summer. Chukkas are clearly the most casual in the selection you proposed and probably better suited to be paired with denim or chinos rather than worsted/woolen slacks and a more rugged sports coat (Tweed, Hop Sack or Linen).

I have a soft spot for saddle shoes ever since I saw a picture of nifty looking Fred Astaire wearing a pair with grey flannel trousers and a navy blazer, but admit I‘ve not found any yet that really look good. Apart from that, they fall into the more classic (read „old school“) category like spectators (which I love to wear for smart casual) that take a bit of guts to pull off these days because they are eye catching.
What are your opinions on wearing a Norwegian split-toe shoe with a business suit (primarily solid navy or charcoal)? What would be the optimal color to get? For context, it would be without a tie (open collar) and the coordinating suit jacket and trousers. I know the cap-toe oxford is the de facto business shoe, but I feel like it's sometimes overkill if I'm not wearing a tie.
 

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