Urban Gentleman Q&A: Advice on Casual Shoes

Question:

Hi

I am currently very gradually trying to smarten up my wardrobe, and I would like to wear more trousers (casually) rather than jeans, with fitted polos, nice shirts, blazers etc. However, I am finding it difficult to find some suitable footwear for such a smart casual look. I like boat-shoes, and will be picking up a navy or brown pair, but they are more kinda summer wear. I find most loafers, mocs to be too formal, so I was wondering to you have any advice on what type of smart-casual shoes can be worn with trousers.


Answer:

Hi (Urban Gent’s name- who’s from England),

I actually had a gentleman email me about a similar dilemma recently- he was trying to find an alternative to the sneaker (so yanno somewhat similar). I advised him to consider:

- boat shoes (sebago/sperrries)
- oxfords
- “dressy sneakers”
- vans (like Pharrell)
- boots

I see that you’re already halfway there since you have purchased a pair of boat shoes (sebagoes/sperries). After securing a pair of those then the type of casual shoe you wear is totally dependent on your style. I am personally a big fan of oxfords- there are so many different styles of oxfords and they easily smarten up the wardrobe.

Other options:
- very casual wingtip lace-up
- drivers
- moccasins (only if this fits your personality)

Here’s a link of examples from Urban Outfitters: click here. Since the pound is almost double the dollar you can easily order from there (but I think you have to add $50 to the total order)… I really like the Schmoove Oxford, the Generic Surplus Oxford, and the Ben Sherman Vacations Lace-Ups.

Drivers are basically the everyday casual shoe for the man that pretty much doesn’t wear sneakers anymore unless he’s going to the gym or participating in an outdoor activity (that’s sort of my view on it anyway). I don’t like all drivers because some tend to look a bit old and dated, but there are plenty that are sleek and stylish- check some of the drivers out at Neimans: click here. From that page I like the Gucci leather driver- 3rd row number 4, the other Gucci leather driver- 5th row number 4, and the Cole Haan venetian moccasin driver- 5th row number 1…. Also I know alot of men that really love the Ferregamo drivers. You don’t have to buy those exact shoes, but those just give you an idea of the styles that may work for you.

If you want a shoe that is, perhaps, a step between sneakers and oxfords then you could try a “dressy sneaker”… basically like a leather converse or designer tennis shoes- Hugo Boss, Lanvin, etc etc (preferably in a solid color).

** this question is a little dated (about a month and a half– so the shoes I’m referring to may not be there anymore or in the same order, but you can still get the general idea).

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3 Comments


  1. GREAT ADVICE.

  2. boat shoes are great all year round, you just need to wear them right.

  3. thanks for taking the time to discuss this i feel strongly about this and i benefit from learning about this subject if possible as you gain facts please add to this blog with more information i have found it enormously useful

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