Fashion Rules To Live By

John LeFevre
8 min readSep 4, 2019


Last year, I wrote a popular fashion article — How To Dress Like a Man. But everywhere I look, when it comes to style, I still see men either trying too hard or not at all. So here is an updated, succinct list for pulling off a timeless and classic look — 125 Style Tips For Men:

  1. Throw out or give away anything you haven’t worn in over a year.
  2. Organize your closet so you aren’t just wearing the same few outfits.
  3. When in doubt, keep it simple. Trying too hard is worse than not trying at all.
  4. Get everything — suits, jackets, dress shirts, pants, jeans — adjusted.
  5. Spend more money on fewer pieces of clothing.
  6. Cedar shoe trees are an absolute must. They absorb moisture, prevent wrinkles, and materially extend the life of your shoes.
  7. Wear an undershirt, even if you don’t sweat. Hygiene and aesthetics aside, they will significantly prolong the life of your dress shirts.
  8. Shop for a suit in person.
  9. Time is too short to do your own laundry.
  10. There is no such thing as turtleneck weather. Circumcise that sweater.
  11. Pants should “break” on the top of your shoes.
  12. Throw all your socks away and buy ten pair of identical socks, and then replenish them every three or six months — because nothing beats the feeling of starting the day off in crisp, fresh, new socks.
  13. The era of baggy shorts is over. Nike is boring and Under Armour is for guys who think Chateaubriand is on a wine list. These are the best shorts on the planet.
  14. Get rid of the college apparel; no one cares.
  15. Facial hair should appear deliberate.
  16. No pant pleats and no cuffs. Ever.
  17. Don’t just burn your Vineyard Vines. Donate them all to homeless shelters until the brand is diminished into irrelevance.
  18. Manscape.
  19. Read more. Wits never sag.
  20. Your phone is part of your look. But skip the case. Phone cases are for the poor and irresponsible.
  21. Knowing how to dress is a skill that can be learned.
  22. Don’t bother with suspenders.
  23. The fleece vest, worn occasionally, is okay. They’re cheaper than a suit, durable, practical in a cold office, and conceal that extra weight.
  24. Other than watches, cuff links, and a wedding ring, no jewelry. The only thing worse for woman than seeing a desirable man with a wedding ring on is seeing a desirable man with with a ring on any other finger.
  25. Wear a tie when you don’t have to. But only with a suit.
  26. Quality sunglasses let women know you appreciate nice things and are responsible enough not to lose them.
  27. Emulate a style icon.
  28. Trade in your wallet for a slim card case.
  29. Gym shoes are for the gym.
  30. Wear a lightweight cashmere sweater under a jacket with some jeans.
  31. Mix it up with colored trousers, but skip the khakis.
  32. No flip-flops unless you’re within walking distance of a beach
  33. Invest in quality luggage. It lasts a lifetime and gets better with age.
  34. Shop with a friend.
  35. Pants beat shorts, even in hot weather.
  36. Buy more shoes than you think you need.
  37. Don’t wear shoes so distinct that they are recognizable underneath a bathroom stall.
  38. Always dress like you might decide to drop by a nice restaurant or bar.
  39. Practice rolling up your shirtsleeves different ways.
  40. Have a few comfortable sweaters or cardigans for cool nights. Most of the time, you’ll end up giving these to a girl. And that’s the point.
  41. Shine your shoes more often than you think you need to.
  42. Use the same moisturizer on your neck that you use for your face.
  43. Starch your formal dress shirts and have them folded in boxes.
  44. Shirt technology — wrinkle-free, machine-washable — has come a long way. Don’t waste money on dry cleaners if you don’t have to.
  45. Try a flamboyant jacket lining.
  46. Own several nice white dress shirts with different textures and collars.
  47. Don’t wear t-shirts with graphics on them.
  48. Invest in an expensive scarf and leather gloves.
  49. Expand your belt collection.
  50. Roll up your ties and store them in a dedicated tie drawer.
  51. Use patterns to flatter your body type. Use broad checks to add weight, or light vertical stripes to add height and slim down your appearance.
  52. Don’t be afraid of pink and lavender.
  53. Shave with a razor.
  54. Sometimes less is more. Plain, dark solid pieces with one bright accent can do more than a flashy, patterned suit or shirt.
  55. And sometimes more is more. It’s okay to go over the top with color and pattern once in a while. But don’t make a habit of it.
  56. Keep the top and bottom balanced. If you’ve got a sleek, streamlined jacket and a simple shirt, don’t wear loose pants with lots of texture. Stay consistent all the way up and down.
  57. Wear seasonal colors. Dark earth tones and shades in autumn, grays and blues in winter, colorful pastels in spring.
  58. Own a formal overcoat, long enough that you can’t see the bottom of a suit jacket.
  59. Buy as many suits as you can reasonably afford. Keep it simple; if a suit has too much flair, the only thing people will notice is how often you wear it
  60. Overdress. There’s nothing wrong with being the best-dressed guy in the room.
  61. Do better than Lululemon. It’s not a men’s brand.
  62. A bad tie knot is like a weak handshake; it shows that you don’t come from good stock.
  63. Learn multiple tie knots. Some are convenient, some are formal, and a few are both. Take pride in knowing how to tie them well.
  64. Ignore trends. They’re a way to separate fools from their money. Keep your look timeless.
  65. If the designer’s logo is too visible, it’s not as stylish as you think.
  66. Don’t be disgusting; replenish your underwear. The average guy only does so once every seven years. Don’t be that guy.
  67. Never wear a suit with sneakers.
  68. Backpacks are for hipsters and school kids.
  69. Keep your jacket buttoned except when you sit. And always leave the bottom undone.
  70. Fix damages sooner, rather than later. Wear and tear looks terrible in public.
  71. A suit is only as good as its tailor.
  72. Keep your jacket on at a bar. People equate sloppiness with drunkenness.
  73. Casual leather shoes make any everyday outfit look more stylish.
  74. Keep yourself well-groomed. And pamper your skin.
  75. Manicures and pedicures are not just for women.
  76. Shirt cuffs should be visible past the ends of your jacket sleeves.
  77. Ties can be fun. Sometimes.
  78. Pinstriped suits always look best with plain white stripes.
  79. Wear the lightest fabrics in the summer. Don’t torture yourself needlessly.
  80. Visit a boutique menswear store you’ve never been to before.
  81. The man purse is never going to catch on.
  82. The shinier your shoes, the dressier they are.
  83. Although bow ties don’t just come in black, save all other attention-seeking options for your son on Easter.
  84. Tie your necktie so that the tip hits the middle of your belt.
  85. Your gym clothes still get looked at. Buy ones you look good in, and replace them before they wear out.
  86. Don’t neglect the importance of swim trunks in terms of functionality, comfort, and fashion.
  87. Dress for the body you have, not the body you want.
  88. Measure yourself only against your previous self.
  89. Stand up straight.
  90. Do 50 push-ups and sit-ups periodically throughout the day.
  91. Manners and etiquette are a reflection of your style.
  92. Loafers are more comfortable and convenient than traditional lace-ups. And the conventional wisdom that they lack formality has long-since expired.
  93. Decent $700 shoes will last 3–4x times longer than something you pick up for $300. Do the math.
  94. If you aren’t confident in your innate fashion sense, keep the shoes black when wearing a suit and a safe shade of brown with business casual.
  95. Statement socks are dumb. They do not add personality or fashion sense. Moreover, pairing, sorting, and color-matching socks is a waste of time and energy.
  96. Get a few custom made shirts. The value far exceeds the cost. Just make sure they are tapered appropriately.
  97. Stick with a stiff spread color; it’s versatile enough to work with or without a tie, and goes with jeans or a suit.
  98. Skip the monogram.
  99. Brown suits are for back office guys.
  100. Buy a tuxedo before you are thirty. Stay that size.
  101. Unless you’re at the game, pro sports apparel is childish.
  102. There is no such thing as a “going out” shirt, especially on a first date.
  103. If you insist on wearing cologne, no one should smell you from five feet away or five minutes after you’ve left the room.
  104. Drink less.
  105. Get your haircut every 4–5 weeks. And if you’ve got problems up top, shave it or transplant it.
  106. Always keep decent facial moisturizer in your desk or gym bag.
  107. Don’t over use pocket squares as a fashion crutch. They should be simple, barely visible, and worn only occasionally.
  108. Leave a jacket on the back of your desk chair so people can never be 100% sure if you’ve left early for the day or are taking a long lunch.
  109. No shirt pockets or collar buttons. The Oxford collar is for college professors, Bernie supporters, and people who still shop at Brooks Brothers.
  110. When it comes to watches, they serve a purpose — presenting yourself as “high-status” is proven to make you appear more attractive to women.
  111. Wearing a Rolex is like driving an Audi. It means you have a little bit of money, but not much to say.
  112. But don’t forget — not wearing a watch is the new Patek.
  113. No need to go above 160 per inch thread count on a suit. Between the abrasive office chairs and the drunken nights out, they don’t last.
  114. You can’t go wrong with a two-button, notched-lapel, single-breasted suit. It’s a classic look that fits nearly every body type.
  115. Skip the three-button suit altogether, and absolutely no double-breasted, unless you still sleep on a waterbed.
  116. It’s a cliché because it’s true; the most expensive suit you own is the one you wear the least.
  117. The blue shirt and white collar is acceptable. This 1980s homage works much better in a light pink or baby blue, and without a tie.
  118. If you like a store or brand, subscribe to their e-mail list for new ideas.
  119. If you’re wearing a blazer, make sure it doesn’t look like a suit jacket. Try a one-button, peak-lapel, which looks great in the office, or out at night.
  120. No gold or silver buttons.
  121. Try brands most people have never heard of.
  122. Save the country club logo polo shirts for the weekend. No one likes to see dudes with dad bods miming golf swings in the office.
  123. Burn your khakis, and wear jeans or a suit instead.
  124. Really good dress shoes make a bit of noise when you walk. And there is evolutionary merit in status-signaling.
  125. Rules are for the obedience of fools, and the guidance of wise men. But remember, fashion rules are usually there for a reason, so use some common sense.

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John LeFevre is the creator of @GSElevator, the founder of a fashion line, a podcast host, and the author of the New York Times bestselling book, Straight To Hell: True Tales of Deviance, Debauchery, And Billion-Dollar Deals, currently in development as a major motion picture.



John LeFevre

Signed contracts with Goldman Sachs and Simon & Schuster, and paid lawyers more than I made. Author of STRAIGHT TO HELL (not about @gselevator or Goldman Sachs)