Example for men. You walk out of a club with your date after an evening of dining and dancing, carefree and enjoying each other, when suddenly a street slug confronts you. Maybe he just wants your wallet, maybe he wants your date, and maybe he wants your life. Whatever the he wants, he must be dealt with. You feel confident you can take him out, so you make your move. Then your shoes slip on the wet concrete, your punch is slower and less powerful because of your tight jacket, and your kick falls short of its target because of the fit of your pants. All your training fails you because of the way you are dressed.
Example for women. You walk out of a club with your friend after an evening of partying and dancing, when suddenly a street slug confronts you. Maybe he just wants your purse, maybe he wants you, and maybe he wants your life. Whatever the reason, he must be dealt with. You feel confident you can take him out, so you make your move. You find you cannot move quickly in high heel shoes, your dress is too tight for you to kick, and your nails are too long for you to make a tight fist. All your training fails because of the way you are dressed.
Soldiers, who are in combat, dress for combat. To be prepared for street combat, you should dress for street combat. This does not mean you need to wear a battle dress uniform with combat boots, but, you are delusional if you think you may defend yourself effectively while wearing constricting clothing.
When dressing for the street, dress appropriate for the weather and the locale. Dress to blend into the crowd, not attract attention to yourself. If you attact attention, you may get more attention than you want.
Everyone wants to dress nice and appropriate for the occasion; however, to be prepared for a possible confrontation, there are some things you should wear, and some things you should not wear.
You should wear fitted clothing that is not so snug that it restricts your movement, or punching or kicking abilities. Clothing should not be so loose that it might it may be grabbed easily and used against you. Clothing should not have anything that could snag on something and hamper your movement. Clothing should not have any parts that could be yanked off and used against you, such as a scarf or cording. Low hanging pants may be in style, but in a self-defense situation, they are a liability. If the opponent pulls them down, it will be very difficult for you to defend yourself with your pants around your ankles.
You do not need to wear body armor, but a leather or denim jacket may offer some protection against a knife attack, as long as it is loose enough for you to move freely. Thin long sleeves do not offer any protection and are a liability because they are more easily grabbed and held than a bare arm would be. There are some fashionable, slash resistant garments, such as jackets and gloves, which may be worn to offer some protection against knives.
Weather often affects your choice of clothing. In hot, humid weather, it is not practical to wear coats or other heavy clothing that may protect you in an attack. Cold weather may give you more choices for proactive clothing, but extremely cold weather may demand clothing that is too heavy and restrictive for self-defense. However, in this case, it probably means the attacker will probably also be wearing heavy clothing that may slow the attack.
Wearing your martial arts school tee shirt or a tee shirt that advertises your martial art is not being inconspicuous. It lets the bad guy know he will need to be more careful when accosting you, and it may mean that he starts the confrontation with club to your head instead of just demanding your money.
Footwear should not heavy or bulky, or have overly thick soles or high heels that prevent you from having free movement. One may think that spiked heeled shoes may be useful when stomped on the top of an attackers foot, but hitting a foot with such a tiny weapon is be difficult when both parties are moving around, and especially so then you are defending against other attacks. The soles of the footwear should offer good traction on most surfaces to keep you from slipping or over rotating on a kick, but they should not have so much traction that they prevent purposeful sliding or rotating. Leather soles are a bad choice under most conditions; they are slippery on practically any surface.
A heavy chain around the neck may be used to choke you. Jewelry draws the attention of attackers, so only wear it in relatively safe situations. The party you are going to may be safe, but the streets outside may not be safe. When in unsafe areas, remove or conceal jewelry.
Ties and scarves
If a thug wants to strangle you, he needs to get something around your throat. When you are resisting, this is difficult to do. However, if you already have something around your throat, the job is half done.
Long hair and beards
Long hair and beards are liabilities when attacked. In a knife fight, the beard may be used to pull the chin up for a throat cut. When fighting, a long beard or long hair may be grabbed and used to gain an advantage. When on the ground, kneeling on the long hair will help keep vitims under control.
Clothing or accessories used as weapons
A belt may be used as a chain whip or a garrote. A metal pen may be used as a spike or knife. A scarf may be used for blocking, grabbing, and choking. A hot cup of hot coffee may be thrown at an attacker’s face. A purse, briefcase, laptop computer, or table may be used can be used as a weapon or shield.
Most fighting knives or other non-firearm weapons are illegal to carry, so you carry them at risk of becoming a criminal yourself. Concealed firearms are illegal except for those who have state issued permits and who are in carrying them in accordance with state law. Unless prohibited by law, almost any weapon may be openly carried but usually there are local laws that limit or control carrying them.
Any weapon is only useful if you have it with you, it is quickly accessible, you know how to use it effectively, and you keep it out of the hands of your attacker. Whether the weapon is carried open or concealed, it must be easily accessible, which means clothing must not hamper its quick deployment. The weapon must be secured to the clothing to prevent the attacker from gaining control of it and to keep it from becoming dislodged when struggling.
You may not dress for street combat all the time, but you should at least keep it in mind anything you are dressing for the street.