1) Your clothes will look better on you if you’re in good shape

If you’re in the middle of a wardrobe overhaul/makeover phase, before you start spending all of your money on clothes, pause for a second. Have a look in the mirror: are you in good shape?

If you’re hesitant or the answer is no, don’t waste your money buying new clothes and spend that money on a gym membership instead. Clothes look better on people who are in shape; that’s how they’re designed. Rick Owens, who, if you’re not familiar, is one of the more influential fashion designers of the last decade, has a great quote that applies here:

“Working out is modern couture. No outfit is going to make feel as good as having a fit body. Buy less clothes and go to the gym instead.”

You don’t have to be jacked, but just make sure that you’re in a position where you feel confident that you’re in good shape. If you feel confident on the inside as a result of being in good shape, then this will project outwards into what you wear, but more importantly, how you carry yourself. Dressing well should be an enjoyable experience, and being in good shape helps to amplify that.

2) Women don’t care about your expensive clothes

It’s a lifestyle myth sold by designer clothing companies that women will desire you more if the price tag on your clothes is higher. While it is true that most designer clothing does look better because of the cut, design, and materials used, what really matters is how you carry yourself underneath all that clothing. Clothing with logos that advertise the brand doesn’t telegraph wealth; they broadcast desperation, which is a very unattractive trait.

There’s a saying: “A rich man should never have to tell you he’s rich, and a smart man should never have to tell you he’s smart.” If your clothing is plastered in logos and you’re clearly fishing for a compliment with it, please reconsider your tactics. Needy behaviour is not a desirable trait.

Clothes make the man, but clothes should not own the man. Instead, focus on finding clothes that fit and look good on your body type and skin tone. Don’t fall victim to logo-heavy clothing just because it’s “designer”. Besides, all of the most expensive designer clothing rarely has logos, so you are only looking pretentious if everything you wear has a logo on it.

3) Don’t buy all your clothes at the mall

This is an abridged version of a previous article. One of the reasons guys tend to avoid caring about how they look is because shopping can be a stressful or boring experience. Whether it’s overwhelmingly large stores, pushy sales associates who do a poor job of relating to their clients, or the exhausting atmosphere of most malls, shopping for a new wardrobe can be taxing on your system. For a change, why not try shopping at a thrift store or searching for clothes online using applications like eBay? Experiences are said to have more profound psychological effects on our happiness than purchasing products do, but what if the two were linked?

By searching at a thrift store or on eBay, you throw in an element of unpredictability to your clothing purchases, and the “treasure hunting” effect can leave you feeling much more satisfied with your purchase. If you are more satisfied with your purchase, you’ll likely be tied to that particular item more, and if that’s the case, you’ll probably enjoy wearing it more. It’s the same feeling you get from wearing your lucky hoodie from college when you go out for a run or toss the football around. If you feel happier about the clothes you’re wearing, that will translate to more confidence, and you’ll look and feel great as a result.

After you purchase something that’s new, the novelty of it being in pristine condition wears off quickly when it gets used, worn, or dirty. Buying clothing second hand is also beneficial because you won’t experience that same feeling of depreciation; your clothes are already used and a little worn, so there’s nothing to worry about if they get a little dirty or look worn.

4) Context is everything: just because you’re dressed up doesn’t mean you’re dressed well

For those of you who took business in school: did you ever have that kid who wore a suit to class in freshman year because he was trying to act “professional”?

This guy would be a classic example of failing to understand context when it comes to wearing clothes. Dress for the situation or else you’ll look like a clown. If you really want to try going outside the spectrum, that’s fine, but you had better have a lot of charisma and self-confidence.

Here’s what you do to look your best based on context. Figure out what the accepted dress code is for whatever situation you’ll be in that day: work, class, wedding, whatever. Figure out the acceptable spectrum that you can dress within, and then always aim for the high end of it.

Are jeans and a sweatshirt the most common thing on your campus? That would be an example of what the middle of the spectrum is, so wear a great fitting pair of jeans and a nicer crewneck sweater to place you near the top end of the spectrum.

Are you going to a semi formal event and everyone is wearing khakis with a dress shirt and tie? Wear a suit without a tie and a dress shirt. This is still semi formal, but you look a lot more put together. The absence of a tie tones down the formality so you don’t dress outside the spectrum. Plus, ties without a jacket always look worse than a jacket and shirt with no tie. Just make sure everything fits properly.

5) Take fashion advice from women with a grain of salt

The old adage is that all women know how to dress well and whatever advice they give their husband/boyfriend on what to wear should be taken as gospel. Not even remotely true; it’s a myth that women are all knowledgeable about this sort of thing. As men, we’ve been forced to believe that caring about how we look is a feminine character trait and should repress it for fear of appearing like a sissy or acting “gay”.

As a man, you should at least have a working knowledge of what clothes look good on you and which ones don’t. Learn what looks good on your body type and skin tone. Declining a woman’s suggestion on what to wear can actually make you appear more attractive, because it will demonstrate your independence and assertiveness. Having a women order you around all the time when you’re rummaging through your closet is not attractive to her or you.

Women are traditionally more gifted in art and other visual-based things, so it does make sense that they are generally better at dressing themselves. That being said, there are many men on the planet who are also very visual-based, and there are many women who aren’t that visual-based. This is not to say that you should completely ignore a woman’s opinion; a second opinion on what you’re wearing may yield a new perspective, but you should at least have the basics down to argue your side of the case.

6) Dressing well means that you’ll look “gay” or feminine

Another stupid stereotype and myth that needs to die. There is zero correlation between being a homosexual male and being well dressed. Yes, there are some well-dressed gay men on the planet, but there are just as many, if not more, well-dressed straight men.

This stereotype stems from the whole argument mentioned in the previous lesson that caring about your appearance means that you will come across as more feminine. Your clothes should not dictate who you are; your actions should, so if you think that you’ll be seen as feminine if you dress fashionably, you won’t, unless you act in a stereotypically feminine manner.

In fact, caring about your appearance and acting like a normal, confident guy, will make you look more attractive. By dressing better than the norm and standing out from the crowd, even if it’s ever so slightly, you take a calculated social risk. This risk makes you vulnerable, both to potential criticism and increased attention. Despite the notion of the word, vulnerability is actually something that men should express more often. I’ll explain: as long as you carry yourself well and don’t act needy or desperate for attention, your vulnerability of dressing will be seen as an attractive trait, and your risk will pay off.

This can backfire, though, so this is why your body language needs to mirror the appearance you wish to personify. Recall the risk of dressing well I mentioned previously. If you dress well but act needy and annoying, you’ll make people dislike more than if you didn’t put in an effort to look good. You may have dressed the part, but because your actions aren’t attractive, the fact that you went out of your way to look good compounds with your unattractive behaviour and makes you look worse overall. In this case, your risk backfired, and this is where the stereotype of men who dress well are seen as high maintenance and overly feminine comes from.

Men are not scrutinized for their physical attractiveness to the same degree that women are; we are judged more on our actions and personality. Even though one of the goals of dressing well is to increase your attraction to others, men need to remember that their clothing is not the single most important factor in the equation. Your clothes will be the first thing people notice about you since appearance. This is the brain’s first step in assessing somebody, but your staying power is rooted in what do say and do after that initial assessment phase.

7) Invest more in things that you wear more often

Makes sense, right? You should invest the most per item in the following order: outerwear, suit (if applicable), shoes, sweaters, jeans/pants (ideally only 1 or 2 pairs of each), dress shirts, casual shirts, activewear.

The reasoning behind this order is that since you will only need 1 or 2 nice jackets, 1 or 2 suits, and 2-3 nice pairs of shoes, you should spend more per item on them. It doesn’t make sense to spend the bulk of your disposable income on t-shirts or gym shorts if you’re just going to ruin them faster by sweating through them day after day. If you’re only purchasing 1 or 2 pairs of jeans, it makes sense to invest in a few nice pairs to last you longer. Your shoes are in constant contact with the ground, but a nice pair will last much longer as long as you take care of them.

You can also look at it this way: the more direct contact on your skin the item has, the less you should spend on it proportionally. Guys sweat a decent amount, so things like t-shirts and even dress shirts wear out the quickest. Your coat, your suit, and your sweaters don’t have the same level of contact with your skin and the sweat it produces as the layers directly against your skin like t-shirts, dress shirts, and undergarments. As a result, they’re likely to last a lot longer, so it makes sense to invest in something nicer, especially considering a nice coat, suit, or sweater adds a lot more statement to an outfit when compared to a nice t-shirt or dress shirt (provided you control for context).

Fashion is a highly subjective field, but I believe these 7 philosophies and guiding principles are universal. I believe that we should all take pride in our appearance the best we can because it demonstrates a great deal of self-respect to the world. These 7 philosophies will help you feel great and feel your best, and hopefully make getting dressed in the morning that much more enjoyable.