How to Dress Well

Recently I’ve realized that most (not all) dudes go about their daily lives not really caring at all about how they dress or how they look. I know, trust me. I was one of them once. I personally feel that if you want to be taken seriously or you want to stand out, or possibly be noticed more by the opposite sex, you need to know how to dress well. Again, trust me. I know. The first time I wore a tie out into the world (excluding bar mitzvahs and funerals) I got hit on. Now that I think about it, that was also probably the first time I’d ever really gotten hit on… That was when it all started coming together. Since then, I think I’ve come to learn a lot about how dress myself and ultimately how to dress well.

First things first. In order to understand how to dress well, you need to first and foremost understand your body type and how to dress accordingly to it. This is probably the most important thing. No matter if you’re underweight, overweight or average, you need to understand the fact that everyone is different and you have a certain body type and you absolutely have to OWN IT. If you’re skinny like me, you do not need to wear overly baggy clothing. It will just make you look even skinnier. You need to wear ‘fitted’ clothing that will flatter your body type. Everyone knows I’m skinny, it’s not like it isn’t obvious. I don’t need to try hide it by wearing bigger clothes. As a guy, you want your clothes to be fitted for the most part. The same thing goes with being overweight. When I say ‘fitted’, I’m not referring to skin-tight. I just mean clothes that actually FIT your body but still give you some (but not too much) breathing room. You don’t want baggy pants that make you look like a clown and you also don’t want pants so tight that you look like a thirteen year old emo kid (sorry thirteen year old emo kid reading this).

Once you have that down, you need to understand how to “dress for the occasion”. This may seem like a no-brainer to most people, but I’ll say it anyway. If you’re not at the gym, or out playing some kind of sport, DO NOT WEAR ATHLETIC CLOTHING. It makes you look lazy. When I say athletic wear, I mean basketball shorts, under armour, sweat bands, or a ridiculous calf high sock + tennis shoe combo. Realize where you’re actually going before you even leave the house. If you’re going out to a bar with some other dudes, you don’t need to wear a three piece suit… unless you want to pass out from heat exhaustion, then by all means. Send me a snapshot or two. Regardless, knowing how to dress for the occasion is a very simple rule that will make your entire social life easier. I hope by now you’re beginning to grasp the sad fact that you can’t wear your “Fuck You Flip Flops” to a five star restaurant.

Moving forward. I’m going to tell you to do something you had never even thought about. ACCESSORIZE. I know this sounds pretty weird if you’re a guy, but it’s true. Girls talk about this shit all the time: “accessories can make or break an outfit”. Again, weird but true. Just wearing a basic v-neck and a pair of jeans today? No problem, add a nice watch or a bracelet or two. Maybe even a sick necklace. This will give people the illusion that you actually tried and thought about your outfit, when you really didn’t put much effort into it at all! Do yourself a favor and invest in a few bracelets and a necklace or two. You can get them from H&M, Topman, asos, YesStyle or even eBay. Trust me, you won’t look back. I would also definitely recommend investing in a nice stylish watch that you can wear everyday that will make you stand out. I have the Jeremy Scott x Swatch Winged Watch. You can even add a pair of sunglasses, a cool hat or even a scarf. I can’t pull a hat off though. I think my head is too small. Maybe I should just buy hats in Asia…

Now I’m going to unlock the final secret for you. I’m making this so easy. If you really want to look incredible without even trying, you need to understand this one thing: LAYERING. Knowing how to layer is a key part of knowing how to dress well. Layers work magic when it comes to dressing for those important interviews, dates, meetings, walking 5th avenue, etc. Remember, you don’t want to look too formal. What you need for your bottoms are: a pair of dress pants or chinos, some casual dress shoes and a belt. Here’s where the layers come into play: the top. To look really good, you want at least three layers. That means a button down shirt or t shirt, a tie or necklace, and some sort of outerwear. Whether it’s a blazer, vest, coat/jacket/cardigan or whatever. This will honestly make you look like a celebrity stylist dressed you or something. It’s that serious.

I know this may all sound like a lot to some of you. The best tip I can give you is this: don’t worry about going out and buying an entirely new wardrobe. Buy one or two key pieces at a time. It’ll save you money and time in the long run, and it’ll keep you from ever having to suffer through an entire day of shopping for a ton of pointless/basic things. More importantly, make sure everything you take home with you makes you feel good about yourself.