Many straight guys are averse to exploring their style and how they dress because they think it’s “gay” or intrudes on their masculinity. It makes most men feel uncomfortable. A lot of men feel set in their ways and don’t like the idea of changing the type of shirts they’ve worn, or the haircut they’ve sported for years and years. They're also intimidated at the idea of standing out or looking too different from the people they hang around.
If this describes you, then it is going to be a mental hurdle that you’ll have to overcome.
Recognize that unless you’ve spent a large amount of time focusing on fashion and style already, chances are what you think looks good right now is not accurate at all. You may think you dress well — hell, everyone assumes they dress well before they know better — but really it’s likely that you don’t.
So the first step is recognizing what you don’t know.
There are a few rules to dressing well:
- 1. Wear clothes that fit.
- 2. Match.
- 3. Dress to your personality
We’ll go through and break each one down, one by one:
Clothes that fit: To start, the vast majority men don’t wear clothes that fit them properly. Men often prefer comfort and practicality to any aesthetic purpose of wearing clothing, so most of their clothing is too big. Chances are most of your clothing right now is too big. Many men are also self-conscious about their body, so they buy large clothing to mask it.
When it comes to clothing, fit is king. You can have the nicest, most expensive clothes in the world, but if they don’t fit well you’ll look like a clown. On the other hand, you can have some modest or even mediocre clothing, but if it fits well (and you’re in decent shape), you’ll look quite good.
Fit makes a massive difference and the change is immediately apparent:
The first step to overhauling your wardrobe should be to go through your closet and pull out anything and everything that does not fit well.
You should always know your measurements. If you’re not quite sure, ask to get measured.
Most clothing department stores have a tailor who will gladly take your measurements for you.
With shirts, the shoulder seam should extend to the end of the shoulder, not any further. If it extends past the end of your shoulder, then the shirt is too big.
On dress shirts, the cuffs should not extend past the wrist bone.
The bottom of your pants or jeans should rest gently on the top of your shoes (unless you have a specific brand – rocker or hip hop jeans). There should not be more than one “break” in your jeans — a break is a natural fold from them resting on the top of your shoe.
If you’re stepping on the back of your pants with the heel of your shoe, they’re too long. If your jeans are raising up to expose your socks when you walk, they’re too short.
Your pants should never sag from your waist when you wear them, even when leaning or bending over. Plumber’s cracks are never attractive.
Jeans should also never slip off your waist without a belt. Most men wear jeans that are too large for them and feel awkward when they first put on a proper fitting pair of jeans. They feel tight and uncomfortable at first. But this is normal. You’ll get used to them in time.
Matching: Guys have an unbelievable knack for being oblivious to colors and how to coordinate them.
Matching is actually simple once you know what to look for:
- Your belt should match your shoes and/or your accessories.
- If you’re wearing dress pants, your socks should match your pants. If you’re wearing jeans, your socks should match your shoes.
- Your accessories must all be gold or all silver.
Here’s an easy way to get started. Go out and buy a “black set” and a “brown set”. Buy a nice pair of black shoes, a nice black belt, and a black jacket. Then buy a nice pair of brown shoes, a brown belt, and a brown jacket.
Then buy a few pairs of nice designer jeans with lighter and darker washes and a dozen or so shirts.
Then it’s just mix-and-match.
You pick a pair of jeans, a nice shirt, and then throw your “brown set” or your “black set” on –
whichever set compliments the shirt and jeans the best. I like to wear the brown set with lighter shirts and jeans, and the black set with darker shirts and jeans.
Of course, dressing gets more complicated than this, but this is an easy and fail-safe way to start out.
Dress to your personality: Dressing to your personality is important to understand dressing well.
Many men learn about fashion and then decide to buy some ridiculous stuff that does not suit
their lifestyle at all: a 40-year-old business executive with baggy jeans and a hoodie, a 20-year old college student with a $500 suit and sweater vest, or just all kinds of random stuff – LED light belts, gold clock necklaces, top hats, etc. It’s amazing sometimes what people think is being stylish when it’s really being outlandish.You are not stylish if you are not dressing to your personality.