101 Gentlemen’s style Tips

I didn’t plan to compile this list, it pretty much wrote itself. I had started to plan out my next articles and before I knew it, I had a pretty good list of headings that also work well as a list of tip style tips. OK so there are a few more than 101 tips here – and if you have some more to go on the list, add them in the comments.


  1. The black Oxford is the most versatile shoe a man can own.
  2. Take pride in keeping your shoes polished, everyone will notice one way or another.
  3. Always match your belt and your shoes.
  4. Invest in shoe trees for all your shoes, they will look better and last longer.
  5. Shoe care is more than just polishing. Storing and feeding are just as important.
  6. Never allow the heels of your shoes to wear down, nothing looks cheaper on a gent.
  7. Invest in a shoe horn and use it to extend the life of your shoes.
  8. A gent appreciates that shoes are an investment, buy the very best you can afford.
  9. Trainers look best in classic plain white or black, that’s when they’re most versatile
  10. If you own black Oxfords, Loafers, brown country Brogues, Chukka boots and plain trainers, you will have shoes for every occasion.


  1. A cleaned & pressed white fitted shirt is the most flattering for most men.
  2. A gent can wear a pink shirt or tie, but never both together.
  3. Shirt sleeves should extend 1/4 to 1/2 inch past the end of your Jacket sleeve. No more, no less.
  4. A gent understands which tie knot matches what shirt collar and wears them appropriately.
  5. A handmade tailored shirt will cost the same as a designer label, but will look so much better.
  6. If you’re unsure which colour suits you, stick with solid colours. Whites, light blues and pinks are the most versatile.
  7. The seam at the top of the sleeve should be in-line with the top of your shoulder. If it goes past your shirt is too big.
  8. White shirts should look white, if they turn grey, bleach them or throw them out.
  9. The key to mastering slim fit is understanding your clothes should still be roomy, just contoured.
  10. Only buy shirts that take collar stays, you will look better for it.


  1. A gent understands what a well-fitting suit looks & feels like
  2. If choosing a ready to wear suit, you still need to take it to a tailors for alterations
  3. Always keep your suit jacket fastened, it is slimming and makes the suit look as it was designed.
  4. Gents over 50 stick to classic cut suits, leaving the shorter trending styles to the youngsters
  5. When wearing a waistcoat, leave the bottom button undone.
  6. When buying off the peg, the hardest thing to alter is the shoulders, get them perfect, the rest can be altered.
  7. If choosing a ready to wear suit, ensure the button hole is not cut with a key hole machine
  8. Charcoal grey, navy blue and black should make the foundation of your suits. After that, the worlds your oyster.
  9. Two button suits are a safe bet, never go for more than three.
  10. Blue suits go best with grey hair.
  11. You jacket sleeve should stop at the bone on your wrist. Any longer is too long.
  12. A charcoal grey suit will be the most versatile suit in your wardrobe.
  13. Take the tags off your suit sleeves
  14. Double breasted suits add bulk to your frame, avoid them if you’re a very big guy


  1. If wearing a jumper over a shirt, ensure the shirt collar is tucked into the jumper.
  2. Gents of all ages will embrace the cardigan
  3. Always leave the bottom button of a cardigan undone, it’s far more flattering.
  4. Always fold your knitwear, it will keep it’s shape better and last longer
  5. A gent appreciates Argyle from his cardigans to his socks!
  6. Hoodies have just been outlawed for the over 30’s


  1. A gent understands the correct length for his trousers and gets them tailored accordingly
  2. Gents over 40 do not wear distressed or faded denim
  3. Don’t use trouser pockets for anything bulky, it ruins the lines of your outfits
  4. Flat fronted trousers are slimming, the more pleats you have the bigger you’ll look.
  5. Wash denim separately and inside out to preserve colour and avoid creases.

Hosiery and underwear

  1. Never wear sports socks unless you are actually doing sports.
  2. Throw out all socks with holes in them, you never know when you will be asked to take off your shoes.
  3. Matching your socks with your trousers will make you look taller.
  4. Make sure your socks are long enough to never show flesh, even when sitting down and cross legged.
  5. Add flair with bold bright socks, but avoid garish pictures or colours. Bright doesn’t have to mean tasteless.
  6. Never let your underwear wear out, you never know who might see them and when.


  1. A gent knows at least four knots for his neck tie and always chooses appropriately
  2. A gent does not wear a digital watch unless doing sports
  3. A gent always a tie clip to a business lunch so as not to get his tie in his soup.
  4. Never wear your sunglasses at night or indoors unless your name is Bono.
  5. Embrace the pocket square, it will add style to any jacket.
  6. A gent knows accessories add flair to an outfit, but you can have too much flair!
  7. It is better to wear no watch than a cheap looking watch
  8. A gent invests in a proper leather bag for the office, and saves his rucksack for hiking
  9. A gent does not mix silver, gold & platinum coloured jewellery in one outfit.
  10. Make sure your tie reaches your waistband exactly.
  11. Invest in quality cuff-links, they will last a lifetime.
  12. Braces (UK) and Suspenders (US) are far better at keeping your trousers up than belts.
  13. Never match your pocket square to your tie, but perhaps your shirt if you are really stuck for inspiration.
  14. A watch doesn’t have to be expensive, but it does have to be elegant.
  15. Don’t just match your belt with your shoes, match your bag and gloves too.
  16. carry a slim wallet with the minimum you need, bulging pockets are not trendy.
  17. you shouldn’t ‘need’ a belt, your trousers should fit. You might ‘want’ to accessorize with one.


  1. you don’t need polar expedition coats when going to the office in winter. Invest in a quality wool coat.
  2. If you need a light weight coat in the summer, a mac or trench coat are classic and stylish.


  1. Get your hair cut frequently so people do not say ‘hey, you got your hair cut’
  2. When buying cologne, test it for 24 hrs. Your body changes the scent over time
  3. A gent knows the name of his barber, his tailor and his doctor.
  4. A gent is comfortable using moisturiser, there is nothing manly about dry skin
  5. Learning to shave with a cutthroat razor will improve your technique with a standard razor.
  6. A gent does not skimp on his weekly grooming schedule
  7. A gent never buys grooming products from a supermarket

General Clothing behaviour

  1. A gent would never leave his clothes in a pile on the floor, he hangs them up.
  2. A gent understands a clothes brush will look after his clothes better than a dry cleaner.
  3. A gent never replaces like for like, he upgrades.
  4. A gent does not wear items with conspicuous branding
  5. Gents in their 20’s should embrace the freedom of youth and experiment to find their best colours.
  6. You should have enough clothes so you never have to wear something two days in a row, even shoes.
  7. Good Posture will drop 10lbs from your appearance
  8. Thrift stores and online auctions can turn up bargains worth investing in.
  9. Prepare for tomorrow today, even your clothes
  10. When dressing well, knowledge is more valuable than money.
  11. Dressing your age is more important as you get older.
  12. Ready to wear is rarely ready to wear. Love your tailor!
  13. The most important thing in dressing well is having clothes that fit perfectly.
  14. Master the basics, great fit and appropriate details and you will be more stylish than 95% of men.
  15. Getting older does not mean wholesale beige and grey, love colour!
  16. If you’re short, go slim fit not baggy to look taller.


  1. A gent never uses abbreviated text language when communicating.
  2. A gent does not refer to a lady as ‘Babe’
  3. A gent does not brag about sexual partners past or present
  4. A gent knows when to stand for a lady
  5. A gent knows when to doff ones hat
  6. A gent never wears a hat indoors unless in the lobby or unless in a public building
  7. A gent does not use his mobile phone in the company of others.
  8. A gent never uses profanity in the presence of others, he is articulate when being expressive
  9. A gent always tips generously when receiving great service, even if it’s not expected
  10. A gent understand which glass is for water and which is for wine
  11. A gent always places his napkin across his lap when dining
  12. A gent always arrives before his date
  13. If a gentleman asks for the date he pays for the meal.
  14. Nothing wrong with personal stereos, but be considerate, keep the volume personal too.

Gentlemanly Behaviour

  1. A gent stays up to date with current affairs, if only to have something to talk about.
  2. A gent keeps a secret and his word no matter what
  3. A gent will always buy the first round, but not the second unless on a date.
  4. A gent is well practised in keeping ones cool in difficult situations
  5. A gent does not keep a tally of drinks bought when out with friends, just to ensure others are paying their share.
  6. A gents car is always clean inside and out
  7. A gent is comfortable with sending hand written thank you notes
  8. A gent does not acquire anything he cannot care for (wife, suit, car, shoes, etc)
  9. When going to a new restaurant, a gent ensures he is prepared and has read the menu in advance.
  10. Rudeness is the weak person’s imitation of strength. A gentleman is never rude


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  1. Great comprehensive list! Every point is truly informative and the way you describe is very simple that everyone can easily understand it was such a necessary read too! I will definitely be passing this information on to my family and friends. Which give basic fashion nearness for every age…
    Thanks for Excellent Post..!

  2. Fashion is most important part in people’s life, its show how you are ? . Fashion never need & come with new era…its nice feel to see you blog, continue with new updates.
    people can visit TRYFA for new fashion update.

  3. What are your thoughts on wearing a suit if you don’t know the dress for the occasion? I meet with clients a lot but I normally just wear a polo. Am I doing this wrong?

    1. Hi Jon, If you don’t know the occasion, I suggest you dress up. It’s very easy to lose a jacket and tie and switch to smart(er) casual, than be stuck in a polo and feel under-dressed.

  4. Good list – which I was so un-gentleman like to share with some of my friends as a much needed refresher.

    In terms of etiquette/gentlemanly behaviour I would like to add the following:

    A gent keeps his private life private and does not complain about his wife/partner to others. If he has a problem, he takes it up with the partner.

    A gent does not gossip nor does he speak poorly of other when they are not around.

    A gent never flirts with others when his wife/partner is around.

  5. I’m only recently coming into the world of dressing well and dressing more gentlemanly so this is a very useful list. Thank you.

    Perhaps a few to add that I’ve picked up…

    An accessory should always be genuine, i.e. never wear clip on ties, or fake pocket squares etc.

    Any functional detail on a suit should always be that, functional, not just for show. (Pockets open but never over filled, working cuffs etc.)

    Last button on a jacket should never be done up. Middle only on a three button though top two are considered acceptable.


  6. Great article. But shouldn’t it be 118 instead of 101?

    I mean I do understand 101 means basic lessons, but if the list would have contained 101 tips it would have been a pun and more interesting.

    Keep up the good work.

    1. Hi Farhan,

      You make a great point. The list was initially posted with only 101 Gentleman’s style tips, but finding a few more, I couldn’t change the title and I didn’t see the point of leaving a few out. Since the article was last edited I have a few more so perhaps I will split them up a bit better in the future.

  7. I enjoyed reading this, thank you. I would love to see more gentlemen in todays age, I think it would be appreciated and respected by young and old. Keep up the good work.

  8. Hello,

    I think the list is pretty good, there were a few I disagreed with, but what I absolutely cannot stand is the photo on the top. The guy’s trousers fit poorly in all the photos (Rule 41), and he is standing with his jacket unfastened in two different photos (Rule 23).


  9. I really enjoyed reading that, and has given me some inspiration to strive to become better. Although, I have to admit, I do have a matching red tie and pocket square!

  10. Woah, stumbled across this massive style tip list and am quite impressed! Awesome job putting this together for men to follow, you’re doing great things here. My biggest tip would be to take care of your clothes, use shoe trees, polish your shoes, iron your shirts, and use suit hangers. Having clothes that are in good condition will only make your style that much better!

  11. Such a comprehensive list! I found every single one of these points informative, knowledgeable, and humorously-written. This was such a pleasant read – but not only that, it was such a necessary read too! I will definitely be passing this information on to my family and friends. We could use more modern gentlemen in the world.

  12. Nice reading, thanks!

    But I’m confused – why should a gent never buy the second round? What about if two gents are out for a drink? I’m not sure I quite got the meaning.

    1. Hi Rob, That’s a great question. Too many people confuse gentlemanly behavior and generosity with being flash with the cash. If you’re out with friends, sure buy drinks, but don’t routinely buy round after round sequentially.

      The obvious exception to this is when you’re on a date. I should probably do a post on this to explain in more detail… Thanks 🙂


  13. What a very elegant list of reminders.

    Lots there that I have either not followed or allowed to drop from my daily behaviours.

    Off to Evernote they go!

    Many thanks.

  14. I am 60 years old and although I am probably well aware of most, if not all of your recommendations, it never hurts to be reminded at any age. A great reference. I thank you.

  15. I enjoyed going through the list, and thought I was doing quite well until I got to the section on etiquette 🙁

    1. Hi Miles, thanks for commenting. This is proof you can’t please all the people all the time. If you want to drop me an email, I am happy to discuss improvements to the list.


    2. Hello Steve, not at all. The list is fine. Really fine. The shortcomings are all mine. That’s what I meant. I fail the etiquette test.

      However I wonder what you think about wearing a pocket square without a tie.


      1. Hi Miles, There is no failing the etiquette test, there are simply things we could do differently. Some people will notice, many won’t, but for those that do notice – it makes it all worthwhile.


  16. Excuse me but you appear to have duplicated in respect of points 60 and 66. May I suggest the following to make up the numbers? When rolling up the sleeves of a long sleeved shirt a gentleman would never roll the sleeves up beyond the elbow.

  17. 28. Black????
    52. You might want to know more than the 4IH and the double 4IH, but you shouldn’t need to actually wear them.

    Otherwise, great advice. Wish that more men read this.

    1. I thought long a hard about adding black, but it’s iconic, underrated and timeless. I’m with you on the tie knots, although it’s always nice to have a repertoire so you can choose should the occasion arise.

  18. Thanks, this is invaluable! You’ve put basically everything one needs to know to be comfortable in the world and to feel justified pride about being this way.

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