Live Action Getup: Black with Brown Smart Casual

Right after “don’t wear white socks with dress shoes,” we’re told not to wear black with brown. And while that’s a good guide when you’re just starting out, pairing the two colors can also look damn sharp.

Black with brown shoes

With a monochromatic color palette, the brown boots inject color, variation, and intention into the look. Black boots could never provide the richness the brown does.

Herringbone blazer, black sweater, jeans, brown wingtip shoes

I've been a fan of JCPenney's Stafford brand since high school. Their Deacon boot is a perennial favorite, loved by internet style aficionados of all income levels. I recently purchased mine on sale for only $60, a great deal considering they're a steal at the regular price of $100. They also have a cap toe version, the Gunner, that you can check out for a boot of a similar profile. If you like the wingtip, Sebago also makes a version for $157.

herringbone blazer, black sweater

Andrew is the founder and editor of Primer. He's a graduate of American University and currently lives in Los Angeles. Read more about Primer on our About page. On Instagram: @andrewsnavely and @primermagazine.

  • anónimo

    Just checked and it looks like the Stafford Deacon’s are in stock, online, for $100.

    • Andrew

      Whoa, that’s perfect timing! Thanks for letting me know.

    • Brian

      I hope you didn’t buy these yet without today’s coupon code…
      That will save you 30%. I’ve seen guys who talk about getting them for $50, but $70 isn’t bad either!

    • Josh

      Just ordered them for $49.99 – $10 with “NOWSAV” = $39.99

    • David

      They are on sale right now for $50. Steal!

  • John

    The key is matching the shoes to the belt; brown with brown, black with black. Doesn’t have to be perfect, but they have to be in the similar. Also, tan, khaki, camel = light brown; grays = various shades of light black. Just don’t wear dark chocolate brown with black, try to be 1 shade or more different, e.g. Dark khaki w/ light gray or black and camel.

    • SolefulStrut

      And how much leeway is there with watch band? I’ve always heard that shoes-belt-watch need to match, but I’ve got a great watch on a black leather band (don’t want to swap to brown) I hardly wear outside of casual sneakers b/c I don’t have any nice black shoes (and don’t feel much need for them).

      • Andrew

        I think there’s some leeway with your watch band. I don’t like all 3 to be of the exact same color, it can stand out.

        • John

          I agree with Andrew. Trying to match all your leathers, i.e. belt, watch band, shoes, jacket, etc. is too much matching. Example, I have a waxed cotton jacket that is almost black (it’s my go to jacket, so it’s got some wear on it). I wear that with brown boots, brown pants, brown belt, and my black watch all the time. The key is that the boots are more of a russet color with the patina of wear on them, the pants are a very dark khaki, the belt is a basic dark brown, but has patina-ed a bit as well. See how all the browns coordinate, but are slightly different in hue? And the watch and jacket are black, or different shades of dark gray.

  • browneagle44 ロベルト

    Currently wearing the Deacons right now! These are my go-to everyday office shoes.

  • Joshua

    Instead of black, would a navy v-neck sweater work? Or would it clash with the denim?

    • Andrew

      Navy would work, just make sure they’re not the exact same color. You could also do a brighter blue.

  • Nick

    I sure wish UNIQLO sold Large in that oxford..I can never seem to win on shirts I want to pull the trigger on! Any subs?

    • Andrew

      Old Navy / Gap and H&M usually have oxfords. Online they’re sold out in Large, but check in store.

  • Tom

    These boots are incredible. Got mine for $50 a year ago and they are holding up nicely. Throw some darker colored shoe polish on there on they will gain depth and character.

  • Miguel

    I have that same jacket. Andrew, did you have yours tailored?

    • Andrew

      Hey Miguel, I had this one brought in on the sides, but I have another Gap jacket that I bought at the same time and the same size that fits great untailored.

      • Miguel


  • Daniel

    Just ordered the boots. $70.

  • James Tollison

    If you buy a Citizen watch, make sure you get one with a readily replaceable band. I had a metal one, and when the third break occurred (I’d already spent $75 on repairs), they told me that the only option I had was to spend $120 to replace the band on a $175 watch. I will not buy Citizen again.

    • Andrew

      I’ve had a Citizen watch for 13 years and have never had any problems with it. I love it, a bummer to hear about your experience.

  • Brian

    I just ordered a pair, shipped to store using promo code “NOWSAV”. Total came to $42.39.

    • Andrew

      Whoa! That’s crazy!

      • Brian

        Especially considering that yesterday was “Green Monday,” supposedly the best deal day of December. Here’s hoping more of your readers are able to take advantage of this deal.

        • Daniel

          I just bought them a second time to get $30 more off. I’ll just return the first order.

  • Daniel

    Can get the blazer at 40% off right now with the code “cozy”.

    • Andrew

      Awesome!! Thanks!!

      • Daniel

        Yeah man, bought the boots and blazer. The rest of the ensemble I have. I also bought the cap toe boots in black as well.

  • Chad

    After reading the comments here and the reviews on the Stafford boots, I had to get a pair. They look good. I hope they are as awesome as advertised.

  • Wyatt

    any other grey oxford shirt like that? They are sold out in my size.

  • Shane

    Love the getup! What’s the best products to take care of those boots???

  • Shane

    Love the getup! What’s the best products to take care of those boots?

    • Andrew

      Any good tan or brown shoe polish will work great on these.

  • Jesse

    Andrew, what is your experience with the sizing of these boots? True to size, order up or down? I’m usually size 11, but 10.5 in a Clark Desert Boot. Thanks.