How to Dress Like a Gentleman: Complete Guide & Top 10 Tips

Wearing tailored clothing 24/7 is not a feasible task – but then what to wear? We’ll show you how to dress like a gentleman in this article. Dressing like a gentleman is not about the style but the fit of the clothing. If you want to wear a casual t-shirt with jeans, you can still feel like a gentleman. You just have to pay attention to a few things.

Man Standing in Front of a Classic Car

If you want to dress like a gentleman, you need to understand two things. What occasion do you attend, and what do you feel the most comfortable wearing. If you like to wear casual attire, you probably won’t feel comfortable in a full three-piece navy suit.

You should wear an outfit that makes you feel comfortable. The most important part of any outfit is the fit, so make sure all of your clothes fit you properly. Casual clothing can be as formal as a plain white shirt. Just follow the rules in the article.

The gentleman lifestyle doesn’t get the recognition that it deserves. That’s why we always write about men’s style and lifestyle tips that help you dress and act like a gentleman. In a previous article, we wrote about The Ten Best Wedding Suits For The Big Day And After.

What clothes do gentlemen wear?

Gentlemen typically wear suits, dress shirts, ties, and dress shoes for formal and professional occasions. Accessories such as cufflinks, pocket squares, and a tasteful wristwatch can further enhance their ensemble.

Khaki Chinos Paired with Burgundy Shirt

For casual occasions, a gentleman often opt for a more relaxed attire, such as well-fitted trousers or chinos paired with a collared shirt or a casual button-down. Comfortable shoes like loafers or clean sneakers are commonly worn, and accessories like belts, watches, and sunglasses can be added to enhance the overall casual yet stylish look.

Keep in mind the fit of your clothing plays a bigger role than the actual clothes you wear. Now let’s see the list that every man should pay attention to if he wants to dress more maturely:

1. Make Sure Your Clothes Fit You

As mentioned, one of the simplest ways to look sharper is to wear clothes that fit you. There is a famous quote – wear clothes, don’t let your clothes wear you.

Gentleman In Dark Suit Sitting Next to Christmas Tree

When you’re buying new clothes, make sure you pick the right size for yourself. But if you happen to find a piece that doesn’t quite fit or if you have some items in your wardrobe that need a little help, it’s worth seeking out a good tailor to lend a hand and make them look great on you.

Nowadays, it is no easy task to find a talented tailor who can help with that, but if you find the right one, they will make quality, long-lasting clothing out of an old loose piece.

2. Wear Clothes That You Feel Comfortable In

If you’ve been wearing the same clothing style for the past years, it’s a good idea to refresh your wardrobe with a few new items. Consider experimenting with slightly more formal options. Investing in high-quality formal attire can result in long-lasting pieces that withstand the test of time.

Man Standing Next To Porsche Macan Dressing Elegantly

3. A Gentleman Pays Attention to the Unwritten Rules

Button rule: There are many unwritten rules to look out for. For example, the button rule on the jackets. On tree button jackets, you can button the top two-button, but never the bottom one. On two-button jackets, you have to button only the top one, but never the bottom one.

If you sit down, you unbutton your jacket. If you stand up, you always button it. The only exception is if you have a casual look, you don’t have to button up your jacket when you stand up.

Jacket Buttoning Rule
Suit Buttoning Rule for Men

Pattern rule: The second unwritten rule is not to mix patterns. Wearing any patterned clothing is okay – just don’t mix and match different patterns. If you plan to wear patterned clothes, pair them with plain items. If you dress casually, you can get away with some mistakes in your casual wear, but if you are visiting any formal events, you have to follow the rules – especially if there are any dress codes.

Matthew McConaughey In Patterned Suit Afternoon Tea The Gentlemen 2019
Matthew McConaughey as Mickey Pearson in © The Gentlemen, 2019

Belt & Shoes Rule: The third unwritten rule is that the belt and shoes should match when you wear leather. An exception to this is white leather sneakers. White sneakers are the most versatile shoes. You can pair them with black, brown, or canvas belts, and they will still look good.

Of course, if you want to go for the most elegant look, you should ditch the belt and wear a suspender or side adjustable pants – but in these case I highly recommend to go with a more classic shoes.

4. Get the Length of Your Pants Right

The length of pants is vital if you aspire to dress like a gentleman. When wearing your finest suit, you don’t want the bottom of your pants to sag or your ankles to show too much. Your pants should just casually sit on top of your shoes.

Man Wearing Black Jeans with Stylish Sneakers
Photo by Alexandra Tran on Unsplash

5. Pay Attention to Details

Paying attention to the finest details is the secret to looking your best. When wearing a suit, try adding a pocket square to complete your outfit. If you want to go the extra mile, a silver tie pin or a stylish pair of cufflinks will contribute to your classy, sophisticated look.

Man Wearing White Shirt with Cufflinks
Photo by Nick Karvounis on Unsplash

6. Keep Your Clothes Clean

It should be an obvious point – always keep your clothes, accessories, and shoes clean. Especially if you want to make a great first impression on your first date. Numerous studies have shown that women check their partner’s shoes, whether they like the fact or not. Trust me. You don’t have to wear dress shoes to impress anyone – you just have to take care of your shoes.

Man Picking Up His Suit From Dry Cleaner

7. Quality Over Quantity

The price of a quality sweatshirt may be three times what you usually pay, but trust me, in most cases, it will last three times – or more. Quality clothing won’t wear out in a year. It’s better to have a few quality pieces than a dozen cheap ones that will look bad after the third wash.

Clothing Store Booth

More money does not always mean better quality. Sometimes that just means it has a big, flashy logo on it – which makes it more expensive. This is not paying for quality, but for brand and status.

8. A Gentleman Knows How to Tie a Tie

Come on, it’s not that hard, and once you learn it, it’s like riding a bike – you will never forget it. It’s time to grow up and learn to tie a tie. If you feel confident with basic tying, you can try new ways to tie a tie.

9. In Winter, Wear Boots, Not Sneakers

It’s more common between younger guys, but in winter, put your sneakers into the bottom of your drawer and put on a good pair of boots. There are many types of boots you can choose from. I am sure there is one that fits your style and requirements.

It’s not only more stylish than any sneaker but will be way better and warmer in the cold weather.

Man Wearing Dark Washed Denim Jeans Paired with Boots

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10. Less is More

Wearing tailored clothing 24/7 is not a feasible task. If you want to wear a casual t-shirt with jeans, you can still feel like a gentleman. Avoid t-shirts with any graphics on them. You can also apply this rule to your accessories. Don’t wear three different bracelets or necklaces. Pick one you like and keep your outfit simple. You can wear casual clothes with stylish accessories, and the result will be perfect.

Man Wearing White T-shirt with Denim Jacket

11. Extra Tip – Wear Subtle Colors

Finally, the key to looking classy is to wear subtle colors. A simple grey or black turtleneck paired with stylish jeans can be as elegant as dress shirts and ties paired with trousers and dress shoes. Navy, olive, and burgundy are always good ideas and look way more expensive than any bold print or bright color in your closet.

How to Dress Like a Gentleman: Wear Subtle Colors

I know it is mostly not visible, but keep subtle colors in your underwear and socks as well – you wouldn’t believe how big of a difference a pair of nice socks can make to your suit.


If you’ve ever asked yourself how is a gentleman dressed – now you know. Being a gentleman is not about the clothes you wear, but how you wear them. You should know when to wear certain pieces and when not. I hope I can help you dress more maturely with this article.

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