•      If you were to pick your top 5 fashion classic pieces, what would they be?

Navy suit, black oxfords or brogues, white dress shirt, Levi’s 501 jeans & white t-shirt 

• I saw an article on your blog about dressing for your 40’s. Could you expand on what the advantages are?

We spend our 20s figuring out who we’re not, our 30s figuring out who we are, and our 40s being it. By the time we hit 40, the “who am I" experimentation should be over. We should have a basically established look and a signature haircut. That’s not to say that there isn’t room for post-40 reinvention if one wishes, but if it turns into one of those clownish clichés where an aging guy looks like he’s trying to keep up with the kids, it looks foolish and sad.

As I approached 40, I felt ripe for a reinvention. I felt like I couldn’t keep up the jeans and sneakers uniform with confidence. This might sound silly, but when I saw Casino Royale, I was reminded how James Bond was always a character men wanted to be, in theory or fantasy. He looks great, in both his suited and casual modes - like a man who cares about his clothes, not a man who cares only about his clothes. I also always admired earlier periods in our culture when men had a higher sense of occasion than they do now. With both examples, we look at the character and the time with a certain wistfulness combined with hesitation. “I would love to look like that, but I couldn’t.” Why not? So I decided to go for it, investing in tailored suits and grown man shoes. I started paying attention to details and to history and to classic notions that seemed impervious to trends. When I started dressing like this more consistently, my life changed - all for the better. People perceived me differently. I made more money. I got better tables in restaurants. Things like that. It’s gotten to a point where I feel quite comfortable in a suit. (And it’s also a matter of respect: respect for oneself and respect for the people, places and things I encounter when I step out.) But I think all of this can be summed up in one word: maturity.

• Do you feel that affordability play a part in developing your wardrobe personality?

Absolutely. I do not subscribe to the notion that style should be expensive or unattainable for normal people. Looking good is not the exclusive domain of the wealthy. In fact, looking better in a $500 suit than the guy who spent $5,000 is not only quite possible, but it's immeasurably satisfying.

• Personally, I feel that the pocket square is one of those style elements that adds so to a look. It seams that there are so many “guides how to style a pocket square” that some men are a bit intimidated. Do you agree that casual is best? Small poof or straight edge fits most occasions without looking like you are trying too hard. #cheap tricks: Get your pocket square poof, twist a rubber band around the other in and pop it in your pocket. BTW, Loved your #cheap trick rubber band on the arm under a suit to hike up the sleeve. Genius.

I love that rubber band gimmick. Such a cheap trick. (And it works!). I love pocket linen, though I don’t always wear it. My preference is cotton so that I can actually use it to clean my glasses or wipe my nose. Form and function. The older I get, the less I fuss over it. The only occasion on which I iron a basic white handkerchief into perfect Mad Men lines is for black tie. Other than that, I like it to look (and be) easy and effortless. 

• A quote from your blog http://georgehahn.com/......“trendy is the last stage before tacky” – Karl Lagerfeld

What is your take?

I’m not one for trendy. I don’t have the budget or the interest. I like classic and timeless. And simple. There’s a reason we revere iconic images of certain movie stars from the past. They looked amazing then, and they’d look amazing now. Just do a Google image search of names like Steve McQueen, Marcello Mastroianni, Michael Caine or the patron saint of timeless men’s style: Cary Grant. That said, a little tasteless accent is okay. To quote the inimitable Diana Vreeland: “We all need a splash of bad taste… No taste is what I’m against."

•I really enjoyed your podcast on wearing suits.
 http://georgehahn.com/category/podcast-3/
•Can you share the highlights?
       Oh gosh, I think I’ll end up repeating myself from my answer to the “dressing your age” question. I love suits. Even more, I love well-tailored suits. As a guy who lives in New York City… Gotham… Metropolis… the Naked City, it is the ultimate uniform for me. A man looks his most elegant in a well-tailored suit. Yet, men seem to fear elegance or being “overdressed.” I’ve been overdressed and under dressed many times in my life. I’d much rather err on the side of overdressed. We live in hyper-casual “athleisure” times, and it’s tragic. It would be a nicer world if we could cure the allergy to elegance.

•       Attainable fashion. The article on your blog http://georgehahn.com/the-new-york-times-mens-style-section-is-great-if-youre-wealthy/ . This article really hit the nail on the head. I feel that great products with style should stand on their own. How does being frugal really pay off?

Circling back to my earlier response on affordability, a man of distinction need not be a real big spender. I am not impressed at all by ostentatious displays of expensive luxury goods. Against the backdrop of our current economic disparity, I actually find it profoundly vulgar. The new Men’s Style section of The New York Times featured an article on singer John Mayer’s watch collection, which is valued in the tens of millions. Super vulgar. Even when someone finds it necessary to flash a designer logo on the frame of a pair of sunglasses, I think it’s gross. Anyone with money can acquire. Boring. What’s more interesting to me is when someone does something fabulous with limited resources. When a movie star on the red carpet has the unshaved balls to step out from the chorus of luxury label whores and answer “Who are you wearing?” with something like J.Crew, Indochino, Suitsupply or even “my custom tailor,” my faith in manhood will be restored.

• What is your pearl of wisdom on style?

When in doubt, ask yourself, “What would Cary Grant do?"

• We truly appreciate you sharing your time and insight.

The pleasure is mine. Thank you for asking!