Here is the kind of outfit that I feel really shows off your summer cool, while looking dandy, sprezzatura and quite different from the crowd (without looking like an ass). It is truly a fashionable and trendy outfit with a classic kick. I couldn't decide on which belt option I liked more... so I gave two different options. This would also look great with a distressed brown leather belt.
A few quick keys to this outfit. Keep the shirt washed don't over due on the ironing. The jacket needs to perfectly tailored. I would recommend a blue linen jacket like this one. Don't be afraid to embrace the wrinkles that the linen jacket will acquire. Make sure the jeans are dark wash and free of holes and other signs of bad trends. I recommend sticking to a slim fit selvedge cotton, like the jeans shown. The red shoes tie the outfit together. They go with the outfit without matching. It is key that you don't wear a red belt as that will look to thought out and perfect. Artful dishevelment is the key to make this outfit look fashionable.
Try this outfit out and tell me later how many numbers girls will give you. If you don't believe me, try it.
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