As you reach your thirties (where I am now) you realize that unless you are in academics or in a creative field, you can’t wear jeans and sneakers everyday, and putting on a suit becomes a daily thing rather than something you do for interviews and weddings. You don’t even try to stick it to the man anymore, because you are fast becoming him (or at least his peon.) But at least you can be the most stylish corporate drone out their. Yup, you may be waiting for the train to arrive to take you to the 8:30 meeting where you are going to get chewed out by the senior partners, but boy, you can look good doing so.
1. A good charcoal suit. Get the best that you can get. If you are (very) well informed about clothes, like to do research, and fancy yourself a bit of a designer, go bespoke. Find one of those rare tailors, choose a cloth from a classic English mill like Lesser, and commission a suit. Otherwise, I suggest you get the best fitting suit you can find. Super lightweight wools are pushed by the Italian designers, but I suggest a solid English cloth instead if you want your suit to look good even after many wearings.
2. A good briefcase. You are (probably) not a secret agent man, so you do not need an aluminum Halliburton briefcase. Get something with the strong whiff of good leather. Do not overstuff it. Your laptop and maybe a portfolio is all you really need. Ghurka uses top notch leather that will age gracefully. The Barrister and Counselor models are classic.
3. A good pen. You don’t need to use it every day, but when you have something worth signing, you don’t necessarily want to do it with a Bic. The best type of pen should have been a gift, but just in case no one has given you one, Waterman is the originator of the fountain pen, S.T. Dupont specializes in beautiful lacquer designs, and Faber–Castell has been making pens since 1761.
4. A Blackberry. I know nothing about these things. I can barely program my cellphone. But all the corporate drone friends I have assure me that they need one of these. My brother (a doctor) tells me that all doctors carry one around to check their diagnosis, which is somewhat disconcerting.
5. A classic pair of sunglasses. Nothing wraparound and nothing that says “My other suit is a wetsuit, bro.” You live in the city. You go to an indoor gym. You have a latte with nonfat milk in the morning with your New York Times. Get something classic from a classic brand like Persol or Oliver Peoples.
6. A good overcoat. This will go over your gray and blue suits, which are, after all, the mainstays of your wardrobe. There are many models. I prefer the rakish Chesterfield, which features a velvet collar and a fly front, in a charcoal herringbone rather than the classic British camel, but the less formal covert coat and raglan coats are also good choices. The classic polo coat, especially the double breasted kind, are best if you are the CEO and own a summer home in Nantucket.
7. Really, really good shoes. If a really big deal falls through, or when your tech stocks crash, you should kick your tires out of frustration with a pair of shoes that cost as much as most people’s rent. So as you throw down your Ghurka briefcase in frustration, let your John Lobbs/Edward Greens/Lattanzis/Kitons/Santoni take the brunt of frustration as you kick your late model BMW. Also good for kicking at the street urchins who ask you for change.
8. A good pair of running shoes. You’re in your thirties. You can’t expect to eat those expense account dinners and not show it on your waistline without some work, right?
9. A watch. Something classic like the I.W.C. Portugese. You are too old to be using your cell phone to tell you the time.
10. A dinner jacket (tuxedo). The best I’ve seen is my Kiton, made for Louis Boston. (Kiton makes a special cut for Louis, I believe). The cut is a perfect blend of the aggressive Italian styling and American casual attitude. Cut from an extremely fine cloth, hardly any shoulder padding at all, high armholes and fitted to the body, but without too much swell in the chest. Single breasted, one button, with sweeping peak lapels that compliment and exaggerate the chest just a little. You are going to need a good dinner jacket for that awards ceremony, even if you aren’t going to win anything. And if you get married, this is the dinner jacket you want to wear at the reception.