Dress for Success: The Most Versatile Men’s Outfit

This week’s Dress for Success selections are the most versatile items you can have in your closet. Whether you’re going to a dinner party, out on a date, or heading into court, pick up these three items and you’ll be well on your way to a great outfit.


The gray suit is the most versatile suit you can own. It’s been said that if you are only going to own one suit, it should be gray. Andrew over at Primer points out, and I agree, that the gray suit is conservative yet leaves plenty of room to bring your own style to the ensemble. Pair your gray suit with a pink shirt, green tie, and brown shoes. It’s a bit of an odd color combination, but it looks great. That look is perfect for a more formal dinner party or a nice date. If you’re going out for drinks after work, you can easily take off your necktie and still separate yourself from the crowd a bit by not being just another guy in a black suit.

I paired the gray suit with brown shoes and a brown belt. Why? First of all, gray and brown look great together; especially when mixed with pink, blue, or green. Moreover, I promised a versatile outfit. These Steve Madden shoes are right on the border between formal and casual. That means they would go great with your suit or a pair of dark jeans. The Cole Haan belt is in the same category. Wear it to work or wear it on the weekends. Either way, wear it and you’ll be dressed for success.

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  • Designer

    Never wear a black belt with brown shoes.

    • If you read the article, you’ll see Josh recommends the brown color of the belt shown.

  • Anonymous

    No, this is not good advice at all.

    Those shoes are truly hideous garbage. If you’re going to buy a shoe for court, it should be a black captoe.

    If you want a more versatile shoe, try a brown or chestnut semi-broogue like the Strand by Allen Edmonds. Steve Madden shoes are generally poorly made, and terribly styled.

    Why not leave your tie on to separate yourself from the slobs who loosen their ties to “still separate yourself from the crowd a bit”?

    Please stop this series if your articles are of such a low caliber, and stick to writing about the law.

  • Josh, I think you should add a sentence to the end of your bio:
    “His courtroom shoes are hideous garbage.”
    That would be sweet.

  • Anonymous

    “Pair your gray suit with a pink shirt, green tie, and brown shoes.”
    Because lawyers should look like plants.

    • I nominate this for best comment of the week!

  • Anonymous

    I have to agree – those Steve Madden shoes are really awful. The sad truth is that to get a decent pair of men’s dress shoes, you’re going to need to spend at least $150 – and that’s if you find a pair on sale.

    Forget about Steve Madden, Stacey Adams, Kenneth Cole, Bostonian, etc. Those are all awful-quality shoes that simply won’t last. Try Allen-Edmonds, Alden, anything from Brooks Brothers, or even To Boot New York if you want to be more high-fashion. But the bottom line is that if you can buy it at DSW or Macy’s, you *don’t* want it.

  • Tyler Durden

    Those shoes are panfully cheesy even if you match them with a “trendy” Ed Hardy suit and a truckdriver hat.

    Seriously, your shoes should be conservative like your suits. For example, Oxfords, wingtips, etc. with subtle detail and no “trendy” flourishes. I don’t even wear tassled loafers because they seem too casual. Save your “style” for the nightclubs.

    Also, belt color should match the shoe color.