Damn son, what you wearing?
Thursday, May 20, 2010 at 1:21PM The summer is tough for a shit ton of reasons. Most men don’t know what to wear in the warmer months and usually don’t care. It’s hot and being comfortable is paramount when it comes to doing things outside. Men dress like crap in the summer, opting for the lowest common denominator when it comes to wardrobe choices. The look is sloppy. But it doesn’t have to be.
I’m a sweater. Once I get going it’s hard to cool down so if in a situation, like being on a roof deck for a BBQ, I need to plan for such things. I would prefer nothing more than putting on some board shorts, a pair of flops and a t-shirt, but that’s not how I roll. If I’m going to be around people in a social situation, there’s a need to look good. Here’s what I wore last weekend. Let me tell you why this works and why I was comfortable.
- Black usually looks classier than any other color so wearing shorts and a t-shirt in dark colors will set you a part and helps you look more polished
- Wearing a blazer and pocket square will ALWAYS make an outfit pop and can dress up anything
- You can always loose the jacket but not until the look has had the time to sink into the party goers minds. At that point it doesn’t matter because you already wowed them.
- If it gets really hot, the pocket square can mop up the sweat
- My t-shit is slighted fitted, fairly new and a very lightweight material so when the jacket came off, I still looked good
- Flops should very simple and small, not clunky man-sandals (which are the dumbest shit. Period.)
- The flops, watch and pocket square all match which elevates the entire outfit
So yeah, I was comfortable, I know I looked good and it couldn’t be simpler to duplicate this look.
Details: Blazer, Ben Sherman * T-shirt, City Sports * Shorts, Reiss * Flops, Gucci * Watch, Toy Watch * Pocket Square, Target (set of three)


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I saw this and had to comment.
Please don't wear this outfit again. Here's why:
1. A blazer with shorts never works. Ever. And the flip-flops make it look even worse. Take off the blazer and you'd look fine. This isn't just my opinion:
http://www.esquire.com/style/fashion-story/mens-fashion-trends-2011-6#slide-7
http://dappered.com/2012/06/is-it-okay-to-wear-a-sportcoat-with-shorts/
http://lagunabeachdjs.com/1/djs-joe-chad-shorts.jpg
2. If you were wearing pants/jeans and shoes, the pants should NOT match the blazer, unless of course you're wearing a suit--if the shades of black are off at all, you look like you're wearing a suit jacket with the wrong pants. So don't do all black unless you have a black suit. The only exception to this would be if the blazer is very casual, like a somewhat faded black cotton/linen. Then it'd look fine with black jeans.
3. A graphic t-shirt with a blazer is pushing it. Some guys won't even wear plain tees with blazers, but I think a fitted plain v-neck looks fine. No graphic tees.