Clothing and Fashion For Men by Hello Sailor TMH

Clothing and Fashion for Men

The Most Awkward Season - Hello Sailor

When the summer comes to an end and the days become shorter, we head into that most awkward of seasons – Fall. What are you supposed to wear when you don’t want to look summery, but it’s too hot to wear long pants and sweaters. I switch over to long sleeve cotton shirts (that I have to iron), roll up the cuffs, and wear light weight trousers.  Having to put your feet back into shoes and socks after your feet have had fresh air all summer is the most difficult of transitions. I practically have to force Danny to start wearing season appropriate clothes.

But then comes that first crisp cool day, and putting back on your layers feels great, and who doesn’t love outerwear? Everyone looks good in layers, even those of us who carry around a few extra pounds. But then it gets hot again and you have dial it back, then it gets cool again, and you have to put it all back on, it gets hot again, etc., etc. With our global warming issues, it’s only going to get worse and awkwarder – is that even a word?

The biggest question is – when is it time to pack up the shorts for the season?  I say by the first of November, regardless of how warm it becomes. When do you stop wearing sandals and flip-flops? I say there is never a good time to wear flip-flops, but my rule of thumb is – the end of September. Cotton sneakers are equally cool and season appropriate.

For years and years, I have always made fun of my glamorous friend Helene V., for wearing so much black. She is a little older than me, but why wear black when there are so many wonderful colors to choose from? Mostly she would tell me to F-off, but she would always let me know when she went to a special event in living color.

I spent the 1990’s mostly dressed in black, gray, and white.  Occasionally I would go neutral, or add a little color. But it got to the point that I had had it with black and moved on to brown and earth tones. Then I over dosed on Brown and earth tones and moved into a short-lived obsession with vivid color. A few seasons ago, I moved on to navy and all shades of blue and gray.  And guess what? Now that I am in mid-middle age – I have gone back to black. Helene V. was right all along.

I find myself drawn to black – not all black – but I do like the contrast of black, white, off-white, navy, and gray.  So long as there is contrast, it is a very classic look, and putting together a look is easy. Is this color story here to stay? – ask me in about ten years.

Alright, people, get with the program and cover those legs and feet, it’s Fall!

Wishing you cool nights and a warm heart,



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