Last month at ESM discussed dressing well even when you’re upgrading from entry-level to middle-level at work as well as your wardrobe.

You are upgrading your wardrobe right?

This month we discuss those men who have sophisticated tastes and the check to match it. This is when dressing becomes more of an art and less of a science.

Closets become dressing rooms. Suit, shirt and tie combinations become ensembles instead of outfits. Purchases are made less and less in a mall and more and more in a boutique, etc.

This is for the connoisseur; the man who appreciates the provenance of clothing and enjoys luxuriating in his sartorial splendor. Take notes.

Suits for the Corner Office 

Custom, Made-to-Order, Made-to-Measure,



You’ve got the coin to spend so go for the gusto and get the best:

  • Having the ability to purchase clothing made especially for you and to your exact measurements is a blessing and a privilege. Use it wisely.
  • Patronize a tailor who understands your lifestyle, career path, and personal attitude. It will pay off in dividends over the years.
  • Invest in fully canvassed suits with handmade details. This is no time for machinery.
  • Wear fabrics in mixtures. Wool/cashmere, silk/linen, cotton/linen, wool/silk/linen, cashmere/ tweed. 
  • Combining high quality fabrics is even more fabulous than wearing them alone.
  • Your rotation should double and you should be reaching the point where a suit is no longer a necessity. Instead it is an extension and outward expression of you. This is where dressing becomes art.

Shirts and Ties

The shirt is the closest thing to your body. It should be glorious.The tie is the only piece of a man’s wardrobe which serves no practical function. It is purely a work of art and should be worn as such.

  • Choose shirts of the highest quality fabrics. Sea Island cotton, voile, chambray, batiste, and linen for summer. Twill, flannel, end-on-end for winter.
  • Play with your collar and cuff styles. English spreads, rounded clubs, tabs, elongated Italian points, soft collars without fusing and/or interlining to give off an air of nonchalance. Barrel, French, convertible, and/or cocktail cuffs are all expressionism at its finest.
  • Monogramming is a plus. At this level it’s nice to have the finer details. Just don’t let them go to head and show off your name anywhere and everywhere. The best dressers are discreet dressers.
  • Since ties serve no functional purpose they should be as beautiful as one can afford. Again fabric mixtures rule. Wool/silk, cashmere/silk, linen/cotton but don’t limit yourself to material. & folds are best and while you’re at it looked for unlined, untipped and hand rolled options. All of these are points of craftsmanship to truly enjoy.

Trousers and Belts

Trousers are overlooked by most men. At this point, you’re not most men. Trousers wear out sooner than jackets and suits. Therefore they should be of the highest quality.

  • Your choice of trousers can make or break your ensemble when wearing blazers and/or sport coats. Make the right impression.
  • Experiment with pleats. Yes, pleats. When worn correctly pleats are a nod to a more classic time. Try one at first, then two. Forward or reverse depending on your stature and taste.
  • Play with your cuff. Most men go with the standard 1.5 inch cuff. We say go for the beefier two inch cuff. This will add a substance to your trousers you’ve never felt or seen before.
  • Forget zippers. The best trousers in the world come with a button fly. Buttoning up is more secure and more rakish.
  • Lining is crucial. Lined pockets, half lined in the front and/or back of the legs. Fully lined to the cuff etc. Lining keeps you cool and/or warm and act as a barrier between you and the outside elements.
  • Forget the belt. Belts hold up those quality trousers but the best dressers don’t wear belts at all. Go with side tabs which hold trousers up without the use of a belt and create a cleaner line. Braces (or suspenders to the less initiated) are also an option. Having nice belts is good. Having nice enough trousers to wear without a belt is nicer.

Dress Shoes

Time and again we’ve said it. A man’s shoes are the foundation of his wardrobe.At this point your foundation should be solid for life.

  • These should be your first purchase. Bench made, made to order, and bespoke is the only way to go.
  • You wouldn't drive your car on bad tires. You shouldn’t walk on them either. Make sure your shoes are Goodyear welted or Blake constructed. These will double the life of your shoes over time and they may outlast you.
  • Leather is just the beginning. Try reverse chamois, deerskin, alligator, snuff suede, oiled calf skin and others.
  • The bottom of your shoe is just as important as the upper. A leather sole for business. Oiled, and flexed welts for casual.
  • Every shoe has its tree. Store your shoes with trees and they’ll thank you.
  • Get tapped. Have a cobbler put hard plastic or metal taps on the toe and heel of your shoes to protect them from the grind of wear and tear. They’re cheap and quick and you’ll be glad you have them later.

Underwear and Socks

Paying attention to your under garments will ensure you still look your best even after you take off your outer shell.

  • Underwear and t-shirts should be of the finest quality. Pima and supima cotton from Peru or Switzerland. Dressing robes and gowns in cotton for summer and wool for winter.
  • Footwear isn’t just for special occasions. Just as a man should not show his uncovered feet outside of the house neither should he roam around barefoot in his castle. House shoes or slippers are a comfortable way to look classy at all times.
  • Socks - not a dog – are man’s best friend. You’ve become accustomed to over the calf. Now expand your options with silk for evenings, boot socks for country, and invisible loafer socks for leisure.


Most men will have a few by now. You should have more and they should be better; make that the best.

  • A true rake takes into account everything the other men do not. This extends to accessories.
  • Umbrellas, gloves, hats, walking sticks, canes, eye glasses, sunglasses, scarves, grooming products. So many options which so many men overlook.
  • Putting time and effort into the smallest of accessories will make the grandest of difference in your appearance.
  • Taking the leap from mid-level to the upper echelon of dressing is a step most men only aspire to. This level of consciousness should be handled with responsibility and grace.

The best clothes in the world are just that;


. The man in them is what the world sees.

(i.e., If you’re going to dress like you’re the shit, you better be able to back it up.)