Dressing Tips for Men on Fancy Holidays

We all want to try different things and to go to different places, but if you want to have fun you will need to have confidence in yourself. And nothing ruins more confidence than a bad outfit. You will be uncertain about yourself, and think that everybody talks about your appearance. So here I will write you down some of the most essential rules you should follow when you’re dressing up. I know that there are enough rules in life as it is. Some, however, (like this one) are here to help you from uncomfortable situations. Of course, every person that has an opinion on such things speaks from personal experience, but those opinions are subjective, no general rules. On the other hand what works for a person may be considered too avant-garde by another. So, when it comes to dressing, always find the most common and general rules and modify them just a bit to create it to your own style.

However, good advice is never to be sniffed at. Also, as menswear becomes ever more appreciated and diverse it can create more moments of confusion and self-doubt, so it’s always a good idea to stick to some general guidelines. These ‘guidelines’ or dress codes tend to be founded many years ago, and they are still actual, so if they worked for other people it will surely work for you as well.

There are certainly many rules out there that will be presented here. Some of these you may actually know, but some might be new for you. First we will show you some general guidelines or rules that are linked to different places or times, and at the end you will see some general rules that can be applied almost anytime anywhere. So without further ado, if you don’t have a girlfriend who gives you dressing ideas read this to have some guidelines about how you should dress on different occasions when you go on holiday.

Boating trip

Nothing feels classier than a boat trip on a luxury boat with a group of friends. You want this occasion to be a memorable day, so you must look ultra-stylish if you are a fashionista in the real sense. The nautical style is not about the changing trends rather it is more about the comfort and matching well of your pieces. A pair of bright shorts and dark tees or short-sleeved shirt is always a good idea to go for something unique that makes your style stand out among everyone around. Don’t be rigid, if you brought a light shirt with you, unbutton it at least to the half. However, this is only for the casual occasions, if you are supposed to have a formal meet-up or business gathering, go and find a light a blazer or a proper suit with hair slicked back.

Cocktail bars

It doesn’t matter if you’re there for a bachelor party, celebrating something or just to have a fun weekend. No matter the occasion, you will need to have a classy but occasional outfit. You can either wear a t-shirt, a long-sleeved shirt, a blazer, just make sure to avoid dark colours. You are there to party, so wear happy colours. However, pay attention to avoid looking like a peacock. The pants can be anything from a pair of jeans to an elegant suit pant, the secret is in the matching colours and styles.


In the previous places you had to be a little occasionally, but here is all about elegance. Nothing brings more confidence in a man than wearing a well-tailored suit. A well-chosen suit can make you feel like Ironman in his armor, where nothing can stop him. You will have to do some research before attempting a casino because there are more types of casinos. The most prestigious ones require a black bow-tie with a black suit and nothing more. But the less reputable ones require only a good suit. You will have to choose a dark colour that can be anything like black, navy or dark grey. A tie is not necessary, but a good pocket square is recommended.

General Rules

  • These are some guidelines, not general rules, you can always overwrite these guidelines by choosing your own style instead. Like all people have their own style, places have their own manners. For example, in Miami, you can show up for an elegant meeting or place in short but in Eastern Europe, you will be ridiculed for such things.
  • Also, if you want to be 100% sure that your outfit is well matched you can always google the specific outfit by entering the right keywords. Also, you can find trendy outfits by following different tags on Instagram or Pinterest.
  • And last but not least don’t forget about accessories. It can define other opinions about you, a well-chosen watch, pocket square, pair of glasses, etc can boost a lot on your outfit.
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