MIDWAY GENTLEMAN

How to Dress Like a Gentleman: The Complete Guide – Our 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.

If you want to dress like a modern 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.

1. Make Sure Your Clothes Fit You

First, 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 buying new clothes, choose the right size for you. Therefore, if you want a piece that doesn’t fit you, or you already have some items in your wardrobe that you want to save but aren’t looking well on you, look for a good tailor and ask for help. Nowadays, it is no easy task to find quality tailors 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

Next, if you’ve been wearing the same style of clothing for a long time, it is time to refresh your wardrobe with a few new pieces. Try a bit more formal outfit. Formal apparel lasts a long time if you buy good-quality pieces.

Man Standing Next To Porsche Macan Dressing Elegantly

3. A Gentleman Pays Attention to the Unwritten Rules

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

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.

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.

4. Get the Length of Your Pants Right

The next tip might be for the fit part, but it deserves a separate point. The length of pants is crucial if you want to dress like a gentleman. If you are wearing your sharpest suit, you don’t want the bottom of your pants to sag or your ankles to show too much. Your pants should just sit on top of your shoes.

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

5. Pay Attention to Details

It 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 you 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.

7. Quality Over Quantity

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

Clothing Store Booth

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 tieing, you can try new ways to tie a tie.

Man Adjusting His 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

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 just as elegant as dress shirts and ties paired with trousers. Navy, olive, and burgundy are always a good idea and look way more expensive than any bold print or bright color in your closet. 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 can a pair of nice socks make to your suit.

FURTHER READING