This week Jordan is on vacation, so Leo gets some peace and quiet in the office, and sets aside time for himself in quiet contemplation of your questions.

You’ve put up with my tyrannical posts for the last 10 weeks now — congratulations for still reading. Hopefully you’ve learned a few things along the way, whether about what shoes to wear, proper colors for professional dress, or how not to overdo it. And a lot of you have been leaving comments and questions to my posts. I appreciate the lively discussion.

Late yesterday,  I got a suggestion from Sam Glover that I should do a piece focusing on the candidates’ dress — whether Paul Ryan’s Dad Pants or Obama’s Hart Shaffner Marx suits. I like this idea, but it requires work, and  I’m feeling lazy.

So instead I’m going to respond to your comments and questions, and grade your answers accordingly.

Let’s get to it.

Button Down Shirts with Suits

Gyi Tsakalakis asks:

At the risk of drawing your snark & ire, I humbly request your attention to the matter of the button-down collar shirt with suit and tie.

A few of you chimed in.

Josh Camson adds:

I agree with the brow-beaters. A button down collar is more casual, and shouldn’t be paired with a suit. But every single person I work with disagrees with me.

Troy decrees:

You shouldn’t wear a tie with a shirt collar that buttons down.

Here’s my response:

Yes, I wore this to court. The world didn’t end.

There are some “style icons” who say “Never wear a button-down collar with a suit!” Hogwash. Button-down collars have been a staple of American business wear for over 50 years. Brooks Brothers claims to have brought the button down to America in 1896, and it can be seen on style icons such as Cary Grant (with french cuffs and ::gasp:: in a double breasted suit!).

Quick, someone tell him he’s breaking “the rules”!

While fashion snoots will insist that it’s improper, they’re wrong. Wear button down collars in health. Brooks still makes seven different classic OCBD (oxford cloth button down) options, made in the  USA — white, ecru, blue, yellow, pink, and red or blue oxford stripe. Stock up. Especially if your office is more the business-casual type.

Grades —

Gyi: A for a good question.

Josh: B- for a half right answer.

Troy: C+ for invoking a “classic,” but wrong, rule.

Learn to Pick Your Own Shirts and Ties

Andrew Karaffa wrote:

…I allow my girlfriend to coordinate shirts and ties. She could spend hours in Men’s Wearhouse and the like, and I get rave reviews on my shirt/tie combo’s. If you don’t have a significant other…my own opinion is, make friends with a girl and let her coordinate.

I hear this suggestion a lot, and it’s almost universally terrible advice.

I want to get one thing off my chest: I really dislike Men’s Wearhouse. It’s like the WalMart of suit purveyors. While they guarantee “you’ll like the way you look,” much of their stock is low grade and cheaply made.

Remember — You get what you pay for.

In fact, The New York Times just wrote a piece relevant to our discussion, which for you “tl;dr”ers out there, can be summed as follows:

There’s a fundamental difference between traditional professional menswear and women’s fashion. Women’s fashion often relies on one or two “pieces” that grab attention. This is the exact opposite of what you should be striving for as a professionally dressed man.

Look at Fred Astaire:

You think Ginger Rogers dressed him?

Classic menswear revolves around looking like a complete package, where each piece complements the other, but none stands out too much. Think of it like a crew rowing a boat — if any one part is too strong, it’ll mess up the course of the ship.

Furthermore, you’re a grown up now. It’s about time you stopped relying on others to pick your clothes. Learn to dress yourself. Don’t rely on others to do the work for you. LIke any thing worth doing, it takes time, practice, and trial and error. Take some time, read up on your Alan FlusserPut This On, or even the Satorialist. See what works and what doesn’t. Remember to Keep It Simple and Sedate.

Grade —

Andrew: C+. You have a plan, but put effort into it and apply your newfound knowledge yourself.

Colors — Shoes and Suits

 Will Geer notes:

…What do you think about wearing a burgundy dress shoe with a charcoal or navy suit? I often view it as the “third shoe” in a man’s collection.

Burgundy (also known as oxblood or cordovan) is a fine color for a men’s shoe. It’s an American color for sure — you’ll likely not see many professionals wearing this color in England, where black shoes still mean business.

(The color “cordovan” actually comes from a special type of leather, shell cordovan, which is made from a membrane from a horse’s rump. Cordovan leather requires a different care regimen than calf, and it’s a bit more expensive, but it ages beautifully. Last I checked, there’s only one tannery in the US that still makes it, Horween in Chicago.).

Your first proper business shoe should nevertheless be a black captoe. Don’t skimp — your feet are worth it.

Grade —

Will: B. Good observation.

Dan Durocher asks:

What are your thoughts on a light gray suit? I noticed it wasn’t a color mentioned in [your] list.

Light grey is a classic color for men’s suits, though going with my larger scheme that lighter suits are generally less formal, it is generally less formal than navy or charcoal. It might not be your best choice for court, or a very traditional law office.

During the spring and summer, you’ll look stylish in a light grey tropical-weight worsted wool suit, white or light blue shirt, and a classic tie. In the colder months, try that same color in a heavier fabric, like a flannel.

Grade —

DanB. Insightful and thoughtful question.

Don’t Dry Clean Your Suits After Each Wear.

Eric Cooperstein is incredulous:

Brush your suits with a horsehair clothes brush after each wearing?! If you can afford the type of suit that would benefit from daily brushing, then surely you can afford to pay someone to do that for you.

There’s a misunderstanding here, it seems. Many men simply dry clean their suits regularly, thinking this necessary. It’s not.

A wise man once said: “What most people today know as dry cleaning is the soaking of dirty clothes in dirty solvent, then fragrantly steamed on a mannequin presser and stuck into a non-breathing plastic bag, hung on a wire hanger. ‘That’ll be $18 for your suit, sir.'”

In fact, dry cleaning is awful for suits. The harsh chemicals strip wool of lanolin (the oils natually present in wool) which causes the fabric to degrade. The heat and pressing ruin the fusible (if your suit is fused). And often, dry cleaners send out your suits for mass washing at an industrial plant where they pay per-piece for cleaning, so no one really cares about your clothes. This doesn’t even consider the environmental and health effects of dry cleaning chemicals.

Instead, avoid that nastiness virtually altogether. Invest in a horsehair brush and a steamer. Brush each suit after wear. If you have some stubborn wrinkles, or you’ve worn a suit a few times, use the steamer to refresh the fabric. For small spills, you can blot with a damp towel. For big spills, give in and take it to a cleaner.

You can drop your dry cleaning bill significantly this way, and prolong the life of your suits.

Grade —

Eric: D. Penny wise, pound foolish.

Let’s Talk “Shoes”

Vincent values comfort:

I just wish I could wear my Vibram FFs to court. They are so comfortable. But trial isn’t about being comfy.

Good call on not wearing them to court. But Vibram Five Fingers aren’t shoes; they’re an abomination. Jeeves disapproves.

Grade —

Vincent: FF.

What About Jordan?

Sam Glover wonders:

Okay, Jordan isn’t really this bad, is he?

A picture speaks a thousand words, so I’ll leave that for the readers to decide:

How would you grade Jordan’s cheesesteak hat?

Until next time, keep up your questions and comments. And keep sending that hate mail to

(photo: Any questions hand written on black board from Shutterstock)


  1. Aaron Street says:

    25% off the Jiffy Steamer on Amazon right now. Honestly, $125 for a clothes steamer will pay for itself in reduced dry-cleaning costs very quickly for most lawyers. Get one.

  2. Josh Camson says:

    I agree about the steamer. I often change in the car or at the gym, and my suits end up getting wrinkled. The steamer is a terrific help with that.

    Never used a brush before. That first one in the Amazon results seems to be geared towards shoes, but I’m assuming it’s the same idea?

    Now, turning to the issue of collars. As you note in your post, the button-down collar is great for an office with a business-casual dress code. Or for squinting at a billboard. That more casual look may be appropriate in Fishtown, but I still believe it is too casual for a courtroom. It’s unclear what the standards are on the Eastern side of the Commonwealth though.

  3. P McGrath says:

    I am sincerely jealous that this many men not only pay attention to how they dress, but discuss and argue over it. If only my husband cared a stitch about how he dresses. Sigh.

  4. Jovan says:

    Did you get the Cary Grant image from my blog? I swear I saved it as the exact same file name as here. ;)

    I do really like that look though. Another example you could have used was Fred Astaire, who regularly wore button-downs with double breasted suits. (Supposedly another sartorial sin, though I’m not sure why.)

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