Everything A Gentleman Needs To Know About Dressing Well Without Breaking The Bank

I get asked questions about my unique style of dress every day. I answer many of those questions here.

Below I answer a lot of questions I get about the way I dress:

You've developed an iconic aesthetic both with your clothing choices and overall lifestyle. What would you consider to be essential elements of your style?

It takes just as much time to be well dressed as it does to be poorly dressed—but the way a man is groomed and dressed is how he presents himself to the world.

The designer Mary Quant once said about clothing, "People like you better without knowing why, because people always react well to a person they like the looks of." It was Mark Twain who said, "Clothes make the man."

It is not true that it is excessively expensive for a gentleman to dress with style and meticulous attention to detail at a reasonable cost. The key to dressing well is firstly to always be properly dressed for the activity one is going to embark on. In other words, don't wear gym clothes to a supper club and don't wear a dinner suit in the gym. Don't wear workout clothes or sweats for shopping or the mall. Always be appropriately clad for what you are doing. If you are in public, you must give some thought to how you are dressed.

The way you dress, mustn't appear studied or as if you've thought about it. The Italians refer to as sprezzatura, a natural ability to thoughtlessly throw together outfits.

One should combine tweeds, plaids, linens, polka dots, blazers, sport coats, and pinstripe double and single-breasted English tailored suits with appropriate shirting and neckwear.

It must all appear as you put it together thoughtlessly—like you "through it together." Gianni Agnelli was the master of this thrown together look of casual high style. This Italian playboy lawyer was the chairman of Fiat and bedded some of the most gorgeous international beauties of the 30s, 40s, and 50s. He famously wore his watch over the cuff of his button-down Brooks Brothers shirt that was always mixed with an understated but finely Roman tailored Italian suit with cream linens in the winter months when he stayed in the Caribbean. Agnelli called himself the "Avvocata," using the Italian word for attorney, which he pronounced as the "Avocado."

Walk us through your styling process. Is it an "effortless" process or do you spend a fair amount of time curating your looks?

As I said, it's a natural process which is thrown together given the fine elements you can assemble online at a reasonable price to utilize in your personal style. 

Very fine gently used or new quality men's style staples can be found on eBay and Etsy. Poshmark has been disappointing lately with their cancellation of purchased items and lack of communication with their customers. 

All the basics of a proper men's attire for both formal and leisure occasions can be acquired or in some places even made, online. 

The Chinese tailor on eBay by the name of "jolenta.1900" will make fine seersucker suits and excellent blazers to your specifications at more than reasonable prices. It is important that you measure accurately and be very specific in your desires.

One must not shy away from the idea that clean, gently or never used garments are not in excellent condition and can be had for a fraction of their original price. 

A navy double-breasted blazer, a gray herringbone three-button sport jacket. A brown herringbone tweed jacket with leather elbow patches. The aforementioned topcoats are all requirements at some point.

You will also need a double-breasted camel hair polo coat, a gray tweed Chesterfield either in fly front or double-breasted style, a naval peacoat, cutaway collar dress shirts, polo style button-down collar shirts, and a solid collection of tasty neckwear. Add an array of high quality used gently or never used neckties in knits, solids, and regimental stripes.

A great trouser starts at the shoulder. That's because a proper fitting pair of men's pleated trousers must be held in place by braces (which Americans call "suspenders") so that the trousers actually hang properly.

High-quality braces or suspenders are harder to find but the most reputable and revered brand is Albert Thurston. 

I have seen some snarky online comments about my trousers appearing "baggy," but those who think so misunderstand the aesthetic—the suit flows. 

The key, of course, is the way the line of your jacket and your trousers fit to create a smooth silhouette. Therefore I prefer a fuller cut trouser that literally hangs at the waist comfortably. This can also work for single and double-pleated khaki trousers, as well as pleated gray flannel trousers—all basic necessities.

Pleats in your trousers can be flattering if the reverse pleat is chosen. Plain front trousers are more available and can look clean, but a pleated fuller cut trouser was a requirement for every suit I've ever had made—although I have not had a new suit made in thirty years.

The cutaway collar is considered more formal, but I have seen Eric Metaxas wear it with a tweed sport jacket with aplomb. 

A short-sleeved knit-collared polo shirt in navy is indispensable - it can be worn with any type of sport jacket and always looks great. Izod Lacoste got this look from actual polo players on Long Island in the 1920s. These can certainly be found online and are still marketed by Polo Ralph Lauren, among others. Avoid ostentatious large logos on the shirt breast, however. These also work in white, red, gray, or wedgewood blue.

It's not just what one wears in public or in the company of others—but what one wears all the time that is a requirement of true personal style. Even when home alone and seeing no one, you have the satisfaction of knowing you are well-turned-out. Fine silk pajamas, silk robes, velvet smoking jackets, the moccasins at MyPillow are excellent (use promo code "STONE"), I order them in black. Again, all these items can be found online at reasonable prices. You can even have your pajamas monogrammed if you so desired. No it is not expensive on-line if you know where and how to shop.

My interest in custom tailoring was initially caused by the fact that in my prime I had 44 inch shoulders but a 31 inch waist—this meant that no suit that was mass-produced, off-the-peg could accommodate both my shoulder without the trousers requiring so much tailoring that the pockets on the back were next to each other. It's unacceptable. This required me to start having clothing made to fit me properly. Having a few classic pieces made and taking good care of them should keep a gentleman well dressed for a lifetime—as has been the case with me. 

A relationship with a qualified tailor who can make simple alterations allows those on the hunt for fashion staple bargains online to purchase at a slightly larger size and have the jacket tailored to fit in the waist and body. When added to the modest costs of acquisition online, you're still paying far less than the fine garment originally sold for. The only unchangeable element in a well-tailored jacket is the shoulder—everything else can be taken in or let out. If the shoulder fits; miracles can be done with a jacket that is slightly too big for you. Miracles can be done by a good tailor.

Unfortunately, because most men's clothing is mass-produced, few manufacturers leave enough fabric in the seams of a jacket to allow the jacket to be "let out." With that being said, any jacket where the shoulder fits but the waste is abundant can be tailored inexpensively. 

Having a few pieces made to your exact fit and specifications or purchasing classic pieces that fit you are the keys to having the basics from which to pluck the elements of your own sprezzatura. 

Again, one does not have to be super wealthy or even rich to dress well if one is willing to take good care of the quality garments they do own and shop diligently for tasteful, basic pieces every gentleman should own.

A young gentleman needs the basic wardrobe of a solid medium or dark gray suit, preferably three-buttoned rolled to two. The same suit in navy, a navy blazer, a tweed jacket, a quality pair of dark gray or medium gray trousers that fit properly, quality khakis (the best are at Bills Khakis), some well-cut jeans, some quality pajamas.

After acquiring some appropriate shirts and neckwear, this basic collection can sustain any gentleman. One can expand into the other highly desirable elements of style I list here as requirements as your finances allow. 

Now we go to socks. It is a sin for a gentleman to show any part of the ankle or leg. You'll need them in navy, gray, brown, and tan. Socks must cover the calves and remain in place. Prior to the invention of polyester, men used ridiculously looking garters to keep their socks in place. 

Some men indulge in a more robust selection of socks that include patterns and checks or other styling. It's a matter of personal taste but I generally stick to the solids. Again, proper length is key.

Angier Biddle Duke was an ambassador and a Brahmin on Philadelphia's Main Line who Esquire and the tabloids regularly cited as the best-dressed man in the country. In fact, Duke owned ten of the exact same dark double-breasted suits and wore the same solid dark navy tie with highly polished wingtips every single day. He had a uniform. It worked, although I don't recommend this route, as his dressing had to get boring even to him.

A monogrammed velvet bedroom slipper is an indulgence if you can afford it. The best are made by Stubbs & Wootton. They can produce a slipper to your personal specifications and do so quickly and are extremely reliable but not inexpensive. Lower price brands can be found on eBay and Etsy. These can be worn in the home or with socks and jeans. Those that I own were custom-made thirty years ago by John Locke - I could scarcely afford them today.

What's the key to making a major entrance?

Sadly, I must usually travel with paid security but the key to dressing well is whether you're going to be seen or not. My friend Jeffrey Tucker said it best, "First, there are clothes for public consumption: clothing in which to present yourself to others and thereby convey an elevated message about yourself. These are types of clothes you wear to work, to the store, out on the town, at a wedding, at church, at parties, or wherever people are going to see you. The primary objective here is that you look presentable, that you are civilized, a gentleman and not a beast." 

What should every gentleman have in his wardrobe?

One indispensable item is the silk knit squared bottomed solid necktie in jet black. It can be worn with any type of collar and, if you are running through the airport to catch a flight and your suitcase breaks open, can be used to tie the suitcase closed. I think this necktie could be used to tow a car—it's a sharp looking staple that works with many great outfits you throw together. Every man must own one. This is an indispensable item.

Another item a gentleman should own is a baker's dozen of fine white cotton handkerchiefs and pull together a tasteful collection of pocket squares, which can be printed, patterned or paisley- one must stuff in their breast pocket as if one hasn't thought about how it looks. Leaving the house without either a white linen or patterned pocket square stuffed in your breast pocket is like leaving the house naked. They are a staple.  

Give us a visual of your closet. What brands, garments, color schemes fill the space?

I've already outlined some must haves for the well-dressed gentlemen. A few others are; a vintage Brooks Brothers or J. Press button-down collar shirt. Brooks Brothers once made the ideal version but as the company changed ownership — belonging at various times to American, German, and Italian owners — the brand changed manufacturing locations so many times that they lost the ability to produce the proper roll of the collar.

The collar was referred to as the "polo collar" because the buttoned button stopped the collar from flapping in the face of a polo player rushing down the field in a chukka. Brooks Brother seized and popularized this button-down collar which originally had a certain insouciant role.

J. Press of New Haven — Brooks Brothers chief competitor — always maintained the proper roll. They still maintain a button on their shirt pocket which I am not a fan of, but they've got the collar right. Kamakura, a Japanese Ivy League company made Brooks Brothers own version better than they did at a much more reasonable price. I turned Larry Kudlow and Charlie Rose on to this company.

Who would you consider the best dressed man in history or today?

I am inspired by the style of Gary Cooper, Douglas Fairbanks Sr. and Jr., Cab Calloway, the Duke of Windsor Edward VIII, Fred Astaire, Rudolph Valentino, Cary Grant, and the aforementioned Gianni Agnelli, among a few.

Fred Astaire was among the great dressers of the 30s, 40s, and 50s. One of the few men so well-dressed that he could break the general rule that one did not wear the less formal button-down shirt with a more formal double-breasted suit. Where generally the cutaway or spearpoint collar is more appropriate for the formality of the suit. Only Astaire could break this rule with aplomb—sometimes topped with a jaunty tyrolean hat, popular in the 1930s.

Astaire would famously throw a new suit or jacket against the wall several times to "knock the newness out of it" before wearing it! His dressing is an inspiration. The idea is not to copy them but to get inspiration from the way they throw together solids, plaids, stripes, and fabrics.

Today, Former White House Economic Advisor Larry Kudlow now of FoxBusiness, is an always incisive tasteful dresser, as is Greg Kelly of Newsmax and WABC. These men are inspirations to any young gentlemen who wants to dress tastefully and well. Mike Smerconish of CNN and Josh Mankiewicz of NBC's Dadeline are always extraordinarily well-turned-out.

I remember meeting you in Miami at a hotel restaurant. You were wearing this perfect combination of patterns; the tie had dots and your suit had subtle striping, etc. I would have never thought to put the pieces together, but you did and it looked absolutely iconic. How do you put pieces together like that? Is it a natural ability?

Again, it's "sprezzatura." You must know the rules before you can break them. Mixing plaids, stripes, and dots can be tricky, but can be done to great effect.

Were you always so bold with your style?

I haven't thought about it. I just believe if you look good; you feel good.

What are some trends that you are into now. Or, perhaps a better question, does Roger Stone do trends? Or is a classic aesthetic always preferred?

One must understand the difference between style and fashion. Style is immutable; it's classic, it's standard—it always works.

Fashion is fleeting. Lapels get narrower and wider. Neckties get wider and narrower. When buying vintage or gently used pieces to assemble your wardrobe, one should avoid extremes in lapel sizes to keep the piece timeless.

The four-inch-wide neckties of the 40s and again in the 70s lack elegance, and as John F. Kennedy, Cary Grant, Sean Connery, and David Niven proved; a trim, elegant knot can be smashing. Connery wore such a solid black knit tie with a three-piece nailhead gray suit as James Bond in Goldfinger—it's perfection. 

I can't emphasize enough how one can piece together a personal style, getting all the necessary basics garments on Etsy, eBay, and Amazon. Live It helps to know one's proper sizes before you find that excellent, high-quality Ivy League and classic style clothing at great prices online. One need not be wealthy to dress well.

Tasteful and proper selection of shoes is also key and the mixing of brown suede shoes with gray or gray pinstripe trousers became acceptable when Edward VIII wore them on a visit to New York City. 

It was there that the Duke of Windsor, Edward VIII also introduced the gray glen plaid double-breasted suit with a blue windowpane overlay. The tabloid media of the 30s made the suit an iconic item and hundreds of designers rushed many fine copies into the market. Some can be found at a reasonable price today. It's a stunning suit every gentleman should own if possible. It also works in a single-breasted style—again, preferably with three buttons... but that's up to you.

The importance of a well-cut navy blazer cannot be underemphasized (in the three or two-button style, and most certainly at least one double-breasted version with fine gold buttons). They can be dressed up with gray flannels or down with well-fitting jeans or properly hanging khaki, gray flannel trousers and even cream linen trousers. The darker your choices, the more formal your ensemble. 

All gentlemen's jackets in the single-breasted style were originally three buttons. It was actually the young John F. Kennedy living with his father, Ambassador to the United Kingdom Joseph P. Kennedy, who invented the two-button jacket, which he had custom-made by fine English tailors while daddy was the ambassador and he was studying in London. The two-button jacket became the staple in American suiting and three-button jackets were still only favored by Italians and Germans.

The buttons on your navy blazers, whether single or double-breasted, must always be both interesting and of high-quality. The standard double-breasted navy blazer has six buttons, although I interestingly found a photo of Prince Phillip with an eight-button jacket. It was exquisite.

Mixing a sport jacket with properly fitting "odd trousers" is less formal than a well cut and commanding suit in the style of Gary Cooper or English movie star Jack Buchanon. Bold beaded and chalk pinstripe suits are always in good taste.

My critics say I look like a Batman villain because I wore a black homburg hat to my federal trial in Washington D.C. Winston Churchill, Dwight Eisenhower, and John Foster Dulles, who popularized this look in the UK and the United States.

One idiotic reporter asked me why I was wearing a "derby"—I guess he meant a "bowler" which, while popular in the financial district in London in the 60s, generally makes one look like a vaudeville comedian. I would never wear one.

The official etiquette for a presidential inauguration requires the wearing of a "morning suit" for the swearing in ceremony, and white tie and tails for the inaugural ball that balls that night. I wore this correct outfit to Trump's 2017 inauguration for which, of course, I was mocked.

The morning coat is the most flattering hip-hugging swallowtail coat a man can wear and is properly paired with striped trousers and a gray or fawn waistcoat which can be either double or single-breasted. A spearpoint, cutaway or a wing collar is paired with a well-knotted silver wedding tie. This is what JFK, Jimmy Carter, Bill Clinton, and Ronald Reagan wore to their inauguration until George H. W. Bush ended the tradition by wearing a nondescript solid blue suit—a major fashion faux pas.

The outfit also requires a top hat which can either be of the collapsible silk type or of a shiny black beaver fur. JFK, who hated and never wore hats, was enamored of the top hat he wore for his inauguration.

In fact, it was JFK who killed the thriving U.S. hat industry which was largely centered in George Bush's Connecticut. Until Kennedy appeared bare headed on the campaign trail, no gentlemen would think of leaving his home for work or leisure without wearing a hat. Overnight, hat sales in the United States plummeted as the bare-headed Kennedy became a national fashion plate and hero.

High quality homburg hats fedoras, as well as fine straw and Panama hats for summer months can all be found online in both new and gently used varieties.

A word about the bow tie. Few men can pull it off. Tucker Carlson could but abandoned it while writer George Will made it his trademark. The blue and white polka-dotted bow tie worn by Winston Churchill is an instant classic. The bow tie, however, must be hand-tied. A clip-on bow tie looks stupid and is strictly verboten. The process of tying a bow tie is the same as tying your shoe and you can master it. The key is for your bow tie to be slightly askew as to show that you hand-tied it. This nuance must be subtle. Bow ties should be avoided with double-breasted suits, but done right, they are a key element of style.

The ascot is another clothing item that not every man can get away with. Most men look like they are a fop or a 1930s Hollywood producer. Carry Grant could pull it off. So could David Niven and Clark Gable. You may want only to sport this look at home!

The Washington Post has never written anything favorable about me in forty years in American politics, however, Robin Givhan wrote this excellent piece for the WaPo when I was standing trial for federal charges in Washington D.C.

Even those who hate me at The New York Times had to acknowledge my personal style. Other than that, their coverage of my trial was inaccurate, misleading, incomplete, and biased. It's the fake news.

For more about how a well-turned gentleman should dress, I refer you to How to Dress Like a Man by Jeffrey Tucker, a seminal piece every gentleman who seeks to be properly and well-dressed should read.

ROGER STONE has a daily webcast at StoneZONE.LIVE every weekday at 5 P.M. ET. Follow him on Twitter at @RogerJStoneJr.

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