Looking stylish in a suit is easy, but what happens when you need to go to a bar or a ball game with your friends? Getting the same look from casual clothes is far more difficult, which is why the vast majority of men end up looking disheveled at best when they are in their relaxed or casual clothes.
But it doesn’t have to be that way. You only need to look as far as celebrities like David Gandy to see that you can look just as stylish wearing jeans as you can in a suit. By picking your clothes carefully, matching colors and ensuring that the fit is on point, you can all but guarantee that you’ll be the best-dressed man in any bar that you walk into.
- 1. Picking the Right Clothes for the Right Situation
- 2. Focus on Timeless Pieces Rather than Trends
- 3. Opt for Versatile Colors
- 4. Don’t be Afraid to Invest
- 5. Ensure that You Get the Right Fit
- 6. Find a Local Tailor
- 7. Try Out More Interesting Pieces
- 8. Don’t Over or Under Accessorize
- 9. Clean Your Clothes Regularly
- 10. Pick a Stylish Pair of Shoes or Boots
- Bonus. Match Your Leathers and Metals Throughout
1. Picking the Right Clothes for the Right Situation
Dressing casually is fantastic. It’s typically comfortable, and it’s much easier than wearing a shirt and tie, but when you choose to dress down, you need to be particularly aware of your environment. There’s a big difference between a downtown bar and your local football game, so, while you might dress casually for both your outfit is still likely to differ.
Knowing when to dress down and how much is arguably the most important step to looking stylish. The simplest way to achieve this is to think what the average person will wear at the venue and then dress one notch above that. For an event where everyone is wearing a t-shirt and jeans, perhaps you could wear a polo instead, or even a patterned shirt.
Similarly, if you’re going to a nicer bar where your friends are going to wear jeans and a collared shirt, you might opt for a stylish pair of suit pants instead which you can dress down with loafers. The point is to match and exceed, not to stand out and look like the exception, but to make others wish that they dressed like you.
2. Focus on Timeless Pieces Rather than Trends
While trends can look great for a short period, by nature, they will come and go. This isn’t to say that you can’t incorporate them into your outfits, but that you shouldn’t rely on them. Instead, by focussing on timeless pieces that have looked stylish for decades, you can give yourself a classic look, prevent yourself from having to buy new clothes each year and ensure that you look stylish month after month.
Two great examples of timeless pieces are a black leather jacket and dark denim jeans. Whether you’re in 1970’s New York City or Ohio this year, you’re going to look stylish wearing dark denim and black leather. These types of clothes are so ingrained in our culture at this point that they have taken on a life of their own and are highly unlikely to ever go out of favor.
What’s great about this is that you can justify spending a little bit more on them because you know that they’re going to last for years to come. As a result, you get to enjoy higher quality clothes that not only look far nicer on you but will also last for longer and are more comfortable to wear. Picking classic and timeless clothes is a win-win with little to no downside.
3. Opt for Versatile Colors
As well as choosing stylish and classic types of clothing, you’ll need to consider the colors too. While trends come and go and with them come a variety of obscure colors and wild patterns, classic colors that are versatile can give you greater use out of your wardrobe and ensure that you wear pieces until they wear out rather than go out of fashion.
Versatile colors are typically rather plain, including white, black, grey, blue, khaki and brown. Not a lot to choose from, right? Well, these aren’t the only colors that you can wear. However, by using them as a basis for your most important clothes like your favorite pants, shoes, and coats, you can ensure that you look stylish.
Then, if you want to incorporate trendy items or different colors you can so sparingly so that they stand out. Picture this, your favorite brown leather loafers, a pair of tailored dark denim jeans, a comfortable black bomber jacket and then a blue and a red hooped t-shirt. By dressing in this way and being conservative with your color choice for your most important clothes you accentuate the trendy items you do choose and still guarantee that you look stylish.
4. Don’t be Afraid to Invest
It’s scary to think about dropping hundreds of dollars on a pair of shoes or jeans, especially if you’ve never spent more than thirty or forty bucks before. But it’s important to remember that not only is looking stylish a priceless thing, but your clothes will also last your for years unlike what you’ve bought in the past.
By thinking more long-term, say over a decade, rather than month to month you can justify buying more expensive and therefore higher quality clothes. The beauty of this is that premium clothing also lasts longer and therefore it’s not unreasonable to assume that you’ll often get better value for money from higher priced items.
One of the best ways to think about clothing is on a per-use basis, in the same way, that you might for a car. A cheap t-shirt might give you fifty uses, at which point it’s shrunk, faded and out of style. Whereas a more expensive shirt might cost ten times as much, but it could give you a thousand use’s or more.
So, as well as having a lower cost per use, you’ll also look far better while you’re using it. Of course, you’ll have to pay more upfront, but that doesn’t mean that you need a lot of money. There’s no reason why you can’t invest in one piece today and then another two months from now, and before you know it you’ll have a far superior wardrobe.
5. Ensure that You Get the Right Fit
As important as your choice and combination of clothes is, there is arguably nothing more essential that a great fit. The world’s most luxurious jeans are going to look terrible on your if they don’t fit, while relatively affordable clothes can look fantastic if they fit like a glove. The key here is to get measured accurately.
Men are notorious for wearing clothes that are either one size too small or one size too big for them. In part because of laziness and also because they might not know what a proper fitting outfit should look like. In general, you want to feel your clothes. If they are loose then you need to size down, if they feel tight or restrictive, you need to go up.
You want them to hug you ever so slightly, but still give you plenty of room to move and be comfortable. If in doubt, take a look online at some of your favorite stylish celebrities to see how their clothes fit and try to emulate it, David Gandy and David Beckham are two great examples.
6. Find a Local Tailor
Unfortunately, the vast majority of men are not going to fit a standard sized piece of clothing because we don’t work out as frequently as we should or have model-like proportions. But luckily for us, a talented tailor can compensate for even the weirdest of proportions to ensure that your clothes look fantastic.
Tailoring doesn’t need to cost an arm and a leg either, often you can spend a few hundred dollars and get your entire wardrobe tailored to fit you perfectly. This decision is ideal if you’re investing in new and better clothes, especially if you plan to wear them for a long time.
It should be noted that if you’re planning to gain or lose a serious amount of weight soon, you might choose to put off buying new clothes and hiring a tailor. There’s only so much they can change, and there’s nothing worse than wasting money.
To find a good tailor you want to look for someone with experience, who has tailored tens of thousands of items and who won’t charge you an outrageous amount. The cost of tailoring will vary from city to city and also depending on your items, but often it won’t cost more than fifteen dollars to do small to medium alterations on the clothes.
7. Try Out More Interesting Pieces
The advice so far has been rather conservative, the point of that is to teach you that you don’t have to do anything crazy to look stylish. It’s typically the opposite, where classic and basic pieces when worn in the right size and color will look best. However, that’s not to say that there is no place for more interesting pieces of clothing.
An easy way for you to look better than everyone in the bar is to pick out more interesting clothes and wear that with your fundamental wardrobe. A great example of this would be the henley shirt, a criminally underappreciated type of shirt that has been worn for decades by some of the most stylish men of all time.
The henley shirt sits between a t-shirt and a polo on a scale of formality, which makes it perfect for a man who wants to look stylish but still dresses casually. If there’s one piece of advice you take away from this guide, buy yourself a long sleeved dark henley shirt and wear it instead of a t-shirt.
Another example of a more interesting alternative to a typical item would be a pair of Chelsea boots instead of dress shoes or even loafers. They are exciting, comfortable and look fantastic with a variety of outfits especially if you opt for a neutral color like black or tan.
8. Don’t Over or Under Accessorize
Accessories are there to accessorize, simple right? Apparently not, because the overwhelming majority of men are either under or overusing them, typically the latter. Wearing three different rings, two bracelets, a watch, and a necklace looks ridiculous and defeats the point of having them in the first place.
Limit yourself to two or three accessories and never wear less than one. A watch should be the obvious choice, but you might also think about things like a hat, necklaces or a bracelet if that’s what you prefer. The point of an accessory is to draw the eye, but you shouldn’t overdo it, which is why subtle metals or leather are ideal.
9. Clean Your Clothes Regularly
While it should go without saying, you need to clean your clothes regularly. Unfortunately, the vast majority of you are probably washing your clothes incorrectly, leading to them wearing out quicker and becoming damaged. If you’re using a dryer for all of your clothes, newsflash, you’re doing it wrong.
Never using a dryer is usually the right choice. It will shrink, fade and cause your clothes to unravel which can half the life expectancy of your clothes, costing you a huge amount of money. For the vast majority of your clothes, a cold or warm wash is best, on a medium spin mode and for a relatively short time. After they are washed, you should take them out when they are still wet and hang them on a rack or a line.
By hanging your clothes when they are wet they won’t stretch or form into an abnormal fit, plus it makes ironing them easier. When it comes to ironing, you should be using a hot temperature, unless you are doing delicates, and you should iron rapidly to prevent any damage. Press down hard or use a hefty traditional metal iron, then fold or hang your clothes and store them.
Remember, items like denim don’t need to be cleaned after every use. Ideally, you can wear them for up to a week or even longer without washing them if you are careful and this can help to extend their lifetime.
10. Pick a Stylish Pair of Shoes or Boots
Footwear is often overlooked by men, given by the number of people you’ll see wearing beautiful outfits with a pair of running shoes. Rather than tripping at the last hurdle, make sure to pick out a stylish pair of shoes or boots that match your outfit and complete it. While leather should be a fundamental part of your wardrobe, suede, and even canvas can look great.
Again, if you want to look better than other men, you’ll need to step up your game. Converse and other sneakers can be great with certain outfits, but you shouldn’t be wearing them every day. Why not try a pair of leather loafers, some Chelsea boots or even Oxford shoes?
Bonus. Match Your Leathers and Metals Throughout
Finally, it’s advisable that you choose a single color of metal and leather. Mixing gold and silver jewelry, for example, looks particularly odd and can leave your outfit seeming cheap, rather than stylish. The same is true for leathers, although it’s arguably less of a problem. Black and brown leather can look weird together while sticking to a single color brings the entire outfit together to look cohesive.
For the vast majority of your outfits, black leather and silver jewelry will look better. So, if you’re on a budget and want to get maximum versatility from a relatively small fundamental wardrobe, pick yourself out a black belt, black boots, black leather shoes, and some silver accessories.