Men's Fashion Trends by Hello Sailor TMH

Hello Sailor Gay Style Tips

 Men's Fashion Trends

Gay style tips for your next gay cruise and keeping your wardrobe in ship shape after 40 from Hello Sailor TMH

As a man in my mid 50's, what I wear today is quite different than what I wore in my 30's and 40's. Back in the day, I was a fashionista as it was important to me at that time. I am an interior designer, and I had the desire to make a statement as a gay man and artist. I was slim, average height and wore clothes well. I took risks mixing and matching all kinds of things and usually pulled it off. I knew what worked on me and had a lot of fun with it.

When new significant others came along, I often had to teach them how to dress. I gave them permission to buy more expensive designer clothes and to have fun with their look. I transformed numerous lives.

Now I'm settled, married to a lovely man, Danny,  for a number of years and have added about 20 pounds to my frame. I did not appreciate my boyish figure while I had it, but I don't mind being a little heavier though I have had to learn to dress for it. My goal is to look well put together but I no longer desire to have all eyes on me. I have also learned that I don't have to spend outrageous amounts of money on my wardrobe in order to look good.


1. WEAR CLOTHES THAT FIT - If all those clothes hanging in your closet are tight in the waist and across the chest, it's time to face reality and donate them to someone who is your former size. Holding onto things until you lose that extra 10 pounds just creates clutter. I recommend you buy for the size you are now, and if you get inspired and lose the extra weight, treat yourself to a new wardrobe. Your clothes should be trim cut but not tight. Don't wear things that are too big even if you are trying to disguise your midsection. No one wants to see a man in maternity wear! Wearing your clothes too baggy will only make you look heavier than you probably are.

2. SKINNY JEANS ARE FOR THE YOUNGER BOYS  - Jeans should be slim cut and flattering to your body but not too tight. Also, make sure they are the correct length - just breaking at the top of your shoes.

 3. AVOID DISTRESSED CLOTHING - You don't want to look like you just stole clothes from a zombie! In my opinion, jeans with ripped knees and holes don't even look good on young people. 

4. SHOES ARE A MAN'S BEST FRIEND - You can take a pretty basic outfit, put on a pair of fabulous shoes and take the look to a whole new level. Invest in good quality classics - lace up boots, driving mocs, loafers, desert boots etc. If you find something fun and trendy that works, by all means, go for it but don't go overboard.

5. HAVE FUN WITH SOCKS - There are all kinds of wild and crazy socks, but they don't necessarily have to match your outfit. I am particularly fond of the crazy socks, but they don't necessarily have to match your outfit. I am particularly fond of the brand happy socks.

6. BELTS SHOULD ALWAYS MATCH YOUR SHOES - You can get away with mixing if they are different materials. For example, a canvas sneaker with a ribbon belt. Don't even ask how much I used to spend on fashion belts at Neiman's!

7. WEAR PRINTS AND A SPLASH OF COLOR - This is a good way of adding a little pizazz but a little goes a long way. A good way to introduce this is a color contrast sweater or a floral print or plaid shirt. Or you can throw all caution to the wind and wear them all together!

8. WEAR COOL FUN GLASSES - This is a great way to add interest to your face especially if you have a thinning hair line. I keep a drawer full of all colors and shapes and always receive a lot of compliments on my eye-wear.

9. DARKER COLORS LOOK GOOD ON OLDER MEN - You can't go wrong with navy, black, dark gray and medium gray. I gravitate to reds and blues as accent colors. You can lighten up in the summer - a pale pink shirt is always fresh and flattering. 

10. INVEST IN GOOD QUALITY BASICS - Sharp outerwear, classic blazers, a hand knit cable sweater, cashmere sweaters etc. You don't need a lot but these produce a large impact on your look.

11. PERSONAL GROOMING IS ESSENTIAL - Make sure your nails are trimmed, smooth and clean. I fight the battle of ear hair every day. Get a good set of tweezers and pluck regularly. There is nothing more gross than tufts of ear hair on a man, and while you are at it, check your nose hairs too as no one wants to see those either.

12. KEEP YOUR BEARD TRIMMED AND GROOMED - If you have a beard, it's a good idea to groom regularly. Keep your neck shaved at all times and shave the back of your neck between haircuts. Keep your eyebrows trimmed but not too close - unless you are a drag queen or desire to look like one! Not that there is anything wrong with that of course :)

13. INVEST IN GOOD QUALITY MOISTURIZER - Apply facial moisturizer, eye cream, and body lotion daily to avoid crow's feet and wrinkles as long as you can. I use these liberally on a daily basis as I'm not taking any chances!

Most of all you want to dress well, live well and be well as we say here at Hello Sailor TMH!

You should always aspire to put in a little time and effort and always try to look your best even when you are tired and grumpy. Above all don't become that sloppy older man you swore you would not become when you were in your prime - back in the day!

Keep it all ship shape and I wish you smooth sailing.

Don Bostick

Creative Director


1 comment

  • Maryanne Mildner

    good writing! …enjoy reading your blog and wearing your comfortable, warm shirts and hoodies.

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