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Shoes for Suit & Smart Casual


Aug 27, 2013
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Hi Guys,

Due to the need to suit up I have started rebuilding my wardrobe and style. In the past few months I have purchased a very nice suit and high quality black cap toe oxfords (Cheaney Lime). Now I am looking to improve my non work wardrobe too and think I should start with shoes. To give you some background I am 26 years old and would like to avoid looking too old-fashioned.

If you want to skip all the details and background info, my questions are all the way at the bottom.

The next pair of high quality shoes I want to buy should be as flexible as possible and go with as many outfits as possible. Here is what I would like to be able to wear them with:

  • Dark gray or charcoal suit (Not sure how to classify mine, please check pictures I have attached)
  • Chinos with shirt
  • Dark straight, tapered jeans with shirt
  • Dark straight, tapered jeans with polo
  • Dark straight tapered jeans with plain t-shirt (I understand that one is a stretch)

To summarise I would like to be able to wear them in the non strictly formal business environment as well as smart casual or business casual.

I have been doing a lot of research and I understand that shoes are more formal
  • the darker they are
  • the less brogueing and decoration they have
  • if they are oxfords with closed lacing as opposed to bluchers/derbys with open lacing

Based on this a dark brown wingtip derby would be the easiest to pair with more casual outfits like jeans and would still work with a suit, but I cannot find one that I like. I also think that most wing-tip shoes look a little too old for my taste.

Therefore I am thinking about buying a dark brown semi-brogued oxford like the AE Strand, Loake 1880 Strand or Barker Flynn. From what I can tell these should work with my suit as well as a smart casual outfit.

What I would like you to help me with is picking a model and color that will work with my suit and jeans.

Picture of my suit:

I am currently in London therefore it will be much easier for me to get the english ones than the AEs. Here are the shoes I am considering:

Loake 1880 Strand


Loake 1880 Byron

The only semi-brogue Derby I could find, but I find the toe is a little too square.

Barker Flynn - Cedar Calf


Herring - Hampstead

Cannot try on. Would have to try on Loakes on the same last and then order

Allen Edmonds - Strand


Another picture of my suit to give you a more accurate idea of the color:

My questions:
  • 1. What colors will work with my suit considering it’s dark gray/charocal?
  • 2. Will really dark brown like Burgundy still work with jeans or is that too formal?
  • 3. What kind of jeans will work best with oxfords? I currently have dark blue low rise, straight jeans with a quite tapered leg, but I am looking to buy new ones in the future.

Thanks guys.

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