Dear Esquire Wears Prada,
I need some help picking out a brown dress shoe. I'd like to be able to wear the shoe both at work and out to dinner or the bar. I'd like it to be a tie - most of my pants have cuffs and loafers look bad with them. I'm looking to spend under $200, but if there is a good argument to be made for spending more, I'm willing to listen. Can you please help?
Thank you for your assistance,
Clueless Shoe Shopper
Oh, yay, a menswear question! We've never had one of those before! This is an EWP first!
While I am a shoe officianado of the highest order, I will admit that while I do have strong feelings about men's shoes, I may not have the ins and outs totally down. So, dear Clueless, I'll have you know that all my choices have been approved by Mr. EWP who considers himself quite the men's footwear expert. So between the two of us, we've got you covered.
I totally understand your desire for a lace-up shoe, and am thinking you'll need an oxford, but not a cap-toe. Cap-toes are too formal for jeans and what you're looking for.
While women can get away with $100 dress shoes, men's shoes really show poor quality at that price point and you have to spend more to get a good quality shoe. No, I'm not saying to spend $1,000 on Mr. EWP's dream shoes (Edward Greene shoes which are only available in England. Yes, he's a weirdo), but I think $180-$350 is about an appropriate price point for the shoes you're looking for. In that price range, you are looking at retailers like Johnston & Murphy or Allen Edmonds -- both are reputable shoemakers, and have storefronts in many cities like Chicago.
Another point -- not all lace-ups are created equal. Stay away from shiny shoes. Often poor quality leather is shined up to hide its imperfections. Plus, let's be honest, shiny looks stupid with jeans.
Regarding color -- Dark brown is probably the most suitable with jeans. Further, a light brown is hard to wear with dress clothes unless you are pretty fashionable or, in the words of Glee's Jesse St. James, "fastidiously groomed." Sorry, I have a compulsive need to reference Glee.
Finally, rubber soles though not usually advisable are typically cheaper than leather soles, more durable, and perhaps may be more appropriate with jeans.
I have some suggestions for you below, but, as always, would recommend trying them on in person and looking at them in real life to make sure they're not too shiny. Hard to tell shininess from online pics.




ae by Allen Edmonds, $199 @

Allen Edmonds, $285 @
@ Available in more colors
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