10 Style Rules That Can Be Broken


Here at RMRS, I always try to teach you the men’s style rules to help you stand above your peers.

You’ve been learning the rules and looking better and better each day.

I would say you’re almost a pro… which is why today I’m going to tell you the style rules you should break to look even better.

I can hear you now – “Antonio, why have I been learning all of these rules if I can just break them?!”

As Pablo Picasso once said, “Learn the rules like a pro so that you can break them like an artist.”

Today, you’re becoming an artist – and here are the 10 men’s style rules you must break to look like a style pro.

  1. Everything Must Match (Leather, Metals, Etc)
  2. No Brown in Town
  3. No White After Labor Day
  4. Don’t Mix Black With Brown
  5. Never Buy A Matching Set (Pocket Sq & Tie)
  6. Never Wear More Than Three Colors/Certain Colors Are Off Limits
  7. Always Wear a Tie When You Ask For Money
  8. Belt Must Match Your Shoes
  9. Only Wear Oxfords with a Suit
  10. Socks Should Match Your Trousers

Style Rule You Should Break #1 – Match Your Metals and Leathers

matching different metals in outfitmatching different metals in outfit

This rule is there to set a standard for the novice. In theory, that’s great, but let’s be honest…

People have:

  • Wedding rings
  • Class rings
  • Family heirlooms
  • Signet rings
  • Watches that have been in the family for generations

Breaking this rule allows you to incorporate more accessories into your outfits. Just because your wedding band is gold – that doesn’t mean you can’t wear your stainless steel watch.

Much like wearing double denim, the contrast has to be bold. This is critical as metals or leathers that are very close in color can look like you don’t know how to match.

You want the contrast to be bold. Announce to the world – yes, I know the rule, but I’m choosing to break it.

Style Rule You Should Break #2 – “No Brown in Town”

man in suit summer timeman in suit summer time

This old British adage held that men should not wear brown clothing or shoes while he was in the city. Brown was considered the color of the countryman. Think tweed and felt hats.

For the English, business meant black – especially as the color of shoes. So if you were wearing brown shoes you would be thought to be off-duty and not ready to work.

The brown shoe has since been accepted and loved. It isn’t easy to go to a professional environment nowadays and not see a brown shoe. Black is still the color that is most worn for formal occasions.

Style Rule To Break #3 – No White After Labor Day

man wearing white clothingman wearing white clothing

This inane rule has its roots in classism.

It’s believed that white was reserved for the financial and social elite. White garments were costly.

After the depression ended and the economy began to rebound, folks who couldn’t afford to wear white suddenly could.

Some say the rule was set in place so that those with “new money” would be noticed and potentially ostracized.

There are elements of this fashion faux pa that are still around. Notice that you don’t see white a lot in stores during the fall and winter months. White shows up in fashion and style when the weather gets warm.

I can’t think of anyone who follows this rule to the letter. Many may do it out of practicality (not wanting to get white clothes dirty during cold and wet seasons), but it’s really not that serious.

Style Rule To Break #4 – Don’t Mix Black With Brown

man wearing brown shoesman wearing brown shoes

One of the most common men’s style rules, this is there to protect the novice.

Black is the most formal of colors, while brown is considered a little more casual. You can easily go wrong with this combination if you opt to wear lighter color brown with blacks. 

But If you know what you’re doing, it can work if you:

  • Are dark skin complected.
  • Make sure the colors are dark enough not to contrast.

For example, you can wear a black leather jacket and add a dark brown chocolate Chelsea boot. Go for it. 

Dark colors work well with each other. It is essential to pay attention to proportionality when wearing these colors.

Style Rule To Break #5 – Never Buy A Matching Set (Pocket Square & Tie) 

man in suit wearing pocket squareman in suit wearing pocket square

When referring to pocket square and necktie matching sets, many aficionados will say, “Don’t buy a matching set; it doesn’t look good.”

This men’s style rule’s actual logic is that it shows a lack of creativity when worn together. It isn’t saying you shouldn’t buy it.

If you understand that and still choose to buy it, you can always wear them separately.  Or if you like the matching set together then go for it!

Most men don’t even wear a pocket square. The fact that you’re actually wearing one sets you apart from the crowd. Confidence will help you overcome 99% of these rules.

Style Rule To Break #6 – Avoid “Un-Manly” Colors

man in pink suit wearing pocket squareman in pink suit wearing pocket square

It was thought to be less manly in the old days if you wore certain colors or too many colors. At the end of the day, it’s all about comfort.

A color is a color – it has nothing to do with your masculinity.

If you are comfortable in pink or lavender, then wear it with pride. There are hundreds of colors and shades of colors that are available to us all.

Certain colors that you can wear can be tricky as well. There is a concept called color blocking but many guys aren’t too comfortable with that.

Color-blocking is a method of style in which opposites on the color wheel are paired together to make interesting and complementary color combinations.

Style Rule To Break #7 – Wear a Tie When You Ask For Money

casually dressed mancasually dressed man

This isn’t a set in stone rule. You should really be concerned with two things when asking for money, and they have nothing to do when neckties.

#1 Know your audience

#2 Never betray expectations

If you’re in a city like Austin, Texas, and you’re meeting with an angel investor, chances are he’ll be in a sports jacket and cowboy boots. You don’t have to mimic his attire, but you can still mimic the formality.

The important thing is to pay attention to the audience & the environment in which you’re asking. Don’t make them feel uncomfortable or betray expectations by severely over or underdressing.

Assess the situation and dress accordingly.

Style Rule To Break #8 – Belt Must Match Your Shoes

This men’s style rule is generally seen as a sign of sophistication and refinement when this detail level was given.

While I believe this should adhere to a professional environment, the rules have relaxed a bit outside of that realm. The browns don’t have to be exact or a tan belt and a brown shoe may work well.

This is also acceptable in casual wear. For example, you can wear a brown or black belt with gray suede loafers.

When your belt doesn’t have to match, you wear sneakers, grey shoes, and navy shoes.

Style Rule To Break #9 – Only Wear Dress Oxfords with a Suit

Close-up of a person's feet wearing elegant brown leather brogue shoes, complemented by grey trousers and blue socks, standing on a city sidewalkClose-up of a person's feet wearing elegant brown leather brogue shoes, complemented by grey trousers and blue socks, standing on a city sidewalk

While it is still preferable to wear formal dress shoes with a suit, there are exceptions. Suits made of 100% cotton and suits made of linen don’t require a pair of leather oxford or wingtips.

Less formal suits can be worn with:

  • Suede brogues
  • Loafers
  • Slippers
  • Moccasins
  • Casual sneakers (this is riskier, approach with caution)

Style Rule To Break #10 – Your Socks Should Match Your Trousers

man wearing suede shoes with blue lacesman wearing suede shoes with blue laces

This rule was for business standards. It’s thought that it was developed to help young lads look the part and not make bad choices when wearing the “professional uniform.”

Also, when socks match your trousers, they have an elongating effect on your legs. It might be prudent for a shorter gentleman to adhere to this rule.

As men’s style has changed and become more relaxed, it is now acceptable to wear a patterned sock that complements your tie or pocket square.

Doing this makes colors in your outfit pop. Socks have moved from an afterthought to a highlight of the outfit now.

Socks with personality have been making waves into style, and it’s safe to say they are here to stay. If you want to take it a step further, you can match your socks to your undergarments.

This, of course, benefits the person you may be getting intimate with later and will be an excellent conversation topic to lighten the mood.

It also helps take the strain of digging through your top dresser drawer for 10 minutes to find socks & underwear. Just grab and go.

Since you already know your men’s style rules (or at least you should), it’s time to break them like a pro. I promise if you break these – you will immediately look better and stand out in a crowd.

You may know your style rules and which ones to break but – do you understand women?

Well, I thought I did, but to be sure, I interviewed a bunch of women to find out what they truly want men to wear… the results may shock you.

Click here to discover exactly what women want you to wear now!

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