I was tossing and turning in bed the other day, unable to fall sleep. In situations like this, most normal people would read a book, count sheep, or just idly lay in their beds till the inevitable sleep haze engulfed their conscience.
Well, I'm a bit weird, and probably not very normal. Thus, as a sleep remedy, I decided to go into my closet and start randomly taking pieces out, just to put them together in different combinations that I thought might work out. Also, I felt compelled to add ties to the mix as well.
It kind of worked, as I was so tired of putting on and taking off clothes that I eventually plopped on my bed and immediately fell asleep.
The outcome is below. And yes, I am actually wearing pants.
The hunter's look.
Jacket: Barbour | Vest: Barbour | Tie: Ovadia & Sons | Shirt: Brooks Brothers
The formal look.
Jacket: Black Fleece | Pocket Square: Nordstrom | Shirt: Brooks Brothers | Tie Bar: Thetiebar | Tie: Theory
The ultra-hyperextended neck look.
Jacket: John Varvatos Collection | Shirt: Black Fleece | Tie: Drake's
The cold day layering look.
Coat: Hugo Boss | Knitwear: Banana Republic | Shirt: Black Fleece | Tie: Theory
The overcoat with suit look... or as I like to call it: blue steel look.
Coat: Banana Republic | Jacket: John Varvatos Collection | Shirt: Ben Sherman | Tie: Ben Sherman
The Looper-ish look.
Jacket: Theory | Shirt: Armani Collezioni | Tie: Thetiebar
The blue, blue, blue, and blue layer look.
Coat: Black Fleece | Jacket: Levi's | Shirt: Brooks Brothers | Tie: Ovadia & Sons
My first thought was to put these photos on reddit, mainly because I was curious to see which outfits vibed well with the huge crowd over there, and which didn't. I put the album up on reddit in the morning, walked away from the computer for about an hour, and then revisited its status shortly afterward.
Apparently the album became quite popular in that hour, ultimately hitting the first spot on /r/malefashionadvice, receiving thousands of up-votes, and getting more comments than I could read.
Turns out that pretty much every single look was simultaneously criticized and praised, showing how incredibly different peoples' tastes are. Some people said my Barbour look was the best, while others thought it was the worst. Some argued that leather jackets should never go with ties, others said leather jackets looked best with ties. Let's just say there was a lot of noise, and it taught me a valuable lesson.
The lesson is that you aren't going to please everybody with your look, no matter how great it is. Sure there are rules that you should follow to look better overall (for example, getting things that are more fitted to your body), but even then, you just aren't going to win everyone's approval, as everyone's tastes are different.
I put together 7 very different outfits, and for each outfit I got hundreds of different reactions. At first, I took each comment constructively, learning from what people had to say. Later on though, all I ended up really caring about was my own opinion, especially after seeing how much contradiction there was about what people thought was right and what people thought was wrong.
I think the best thing is for you to feel confident in the clothes that you wear, and present your unique style to the world expecting nothing in return. Sure, positive reinforcement may help you feel better, but ultimately, I think the most attractive thing about someone's style is how they own their look. The swagger and confidence they have in wearing what they are wearing. The great thing is that no one can help you own your look, only you can.
Anyhow, sorry to go on a rant there, but I hope I was able to at least provide you with some ideas for outfits. Oh, and just kidding about the pants comment I made above. Commando all the way.