How to Dress Like a Gentleman: Complete Guide & Best Tips

Dressing like a gentleman involves the style and the fit of your clothes. Even in a casual T-shirt and jeans, you can feel like a gentleman by following a few key rules.

Man Standing in Front of a Classic Car

If you want to dress like a gentleman, you need to understand two things: what occasion you are attending and what 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.

Wearing a comfortable outfit is essential; it not only boosts your confidence but also improves your overall appearance. One of the crucial elements of any outfit is fit, so ensure that all your clothes fit you properly. Casual clothing can be as stylish as a plain white shirt, as long as you follow the guidelines mentioned in the article.

1. Make Sure Your Clothes Fit You

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

When buying new clothes, make sure you pick the right size for your body type. However, 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.

Gentleman In Dark Suit Sitting Next to Christmas Tree

Semi-bespoke clothes will look ten times better on you than any other off-the-rack clothing, and they will make you feel awesome every time you wear them because you know they are tailor-made for your body.

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

A refined man respects the unspoken rules that define life’s subtle nuances, such as jacket buttoning, pattern mixing, and leather matching, which, though rarely discussed, should not be disregarded.

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If you want to dress like a gentleman you should learn to pay attention to these unwritten rules:

Suit Jacket Buttoning Rules

There are many unwritten rules to look out for. For example, the buttoning rule on jackets. On three 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

We’ve made a separate article about how to wear a suit like a gentleman, make sure to read it for a more detailed answer about fashion rules.

Pattern Mixing 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 or matching patterns.

If you dress casually, you can get away with some style mistakes, but if you are visiting any formal events, you have to follow the rules – especially if there are any dress codes.

Dress Like a Gentleman: Match Patterns
Matthew McConaughey as Mickey Pearson in © The Gentlemen, 2019

Match Your Leathers

The third unwritten rule is that your leathers should match. This usually includes the belt and shoes, but if you are wearing leather accessories such as a watch, it should also match your outfit.

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.

Dress Like a Gentleman: Match Your Leathers
Photo by Hermes Rivera

Of course, if you want to go for the most elegant look, you can skip the belt and wear a suspender or side adjustable pants – but in these cases, I highly recommend going with 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.

Dress Like a Gentleman: Wear Well Fitting Clothing
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.

Dress Like a Gentleman: Pay Attention to Details
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 it or not. So, the next time you go on a date, make sure your shoes are clean. You don’t have to wear your most expensive dress shoes to impress anyone – you just have to take care of your shoes.

Dress Like a Gentleman: Keep Your Clothes Clean
A Man Cleaning a Navy Blue Suit © Suits Co

The same applies to other garments as well; avoid wearing clothes with stains on them. If you plan to wear a suit, make sure it is properly cleaned, and if you are not sure, take it to a local dry cleaning place.

7. Buy Quality Over Quantity

The price of a quality sweatshirt is maybe three times what you usually pay, but trust me, in most cases, it will last three times – or more. Good 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.

Dress Like a Gentleman: Buy Quality Over Quantity

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 high 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.

Once you learn how to tie a tie, you can learn how to break wearing them. A gentleman also knows when and how to skip the tie.

9. In Winter, Wear Boots, Not Sneakers

While it’s more typical for younger men to wear sneakers in winter, older men often opt for lightweight sneakers as well. Gentlemen, during winter, put away your sneakers and opt for sturdy boots. There are many boot styles available, ensuring a suitable choice for your style and needs.

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

Dress Like a Gentleman: Wear Boots Instead of Sneakers

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. You just need to look out for a couple of rules. Avoid t-shirts with any graphics on them and try to choose a subtle colored top. 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 a perfect smart casual outfit.

Dress Like a Gentleman: Less is More

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.

Dress Like a Gentleman: Wear Subtle Colors Like Burgundy, Navy, and White

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

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 opts 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.

How Should a Gentleman Dress?

A gentleman should dress in a professional, sophisticated, and tailored manner, reflecting a sense of style and respect for the occasion. Keep in mind the fit of your clothing plays a bigger role than the actual clothes you wear.

Men Sport Coat Jeans Outfit

Now let’s see the rules that every man should pay attention to if he wants to dress more maturely:

How to Dress Like a Gentleman Without Looking Old?

If you are a young guy and afraid of looking old, I understand you; there are certain clothes that best fit a more mature man, but don’t worry, there are many clothing items that a young gentleman can wear, such as a plain dress shirt, a collared shirt, a nice pair of pants, stylish white sneakers, or a tailor-made suit, which are classic items suitable for any age.

How to Dress Like a Gentleman


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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When you dress like a gentleman, you exude an air of confidence and self-assuredness that commands respect in any setting.

Keep on reading: How to Live a Gentleman’s Lifestyle

How to Dress Like a Gentleman: Complete Guide & Top 10 Tips
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How to Dress Like a Gentleman: Complete Guide & Top 10 Tips
Wearing tailored clothing 24/7 is not a feasible task – but what to wear then? We'll show you how to dress like a gentleman in this article.
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Midway Gentleman
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