I have been somewhat of a clothes horse since I was a teen aged, now somewhat a youthful looking guy in my mid 50’s (my closest celebrity doppelgänger is Joe Scarborough). In a certain sense, being older frees you up to not jump on to every trend and hopefully age has given you the self awareness to dress for your body type rather than try and squeeze into something that while fashionable, looks ridiculous on you ( The late Scott Weiland (lead singer of the Stone Temple Pilots) was quoted as saying “There are a limited amount of years in which you can wear skinny jeans, There comes a point where whether you can or not, you shouldn’t “. I’ve got nothing against skinny jeans per Se for young men that are, well, skinny. I was rocking that look about five years ago and then I caught a look at a young guy who was built like me wearing some Levis 511’s and thought he looked like a California raisin, then I had an “oh shit” moment and out went the 511’s to be replaced by 501’s and 514’s (straight legs, see my previous post on Denim).
It is ok to stick with or go back to classics. In college and law school 83-90, I wore Levis 501, Ralph Lauren polos and button downs and Sperry Top Sider boat shoes and sneakers. Today I wear pretty much the same thing. The cut may change but it’s a classic look. That’s the key word, classic. Nobody wants to see the 40-50 something wearing a logo skinny tee. Clever Graphic tees are awesome for 30 something single guys to wear to brunch. They look sad on the 52 year old at the Catholic High School parents social. Same thing with shoes. I love Vans and the fact that my teenage boys wear them. I wore them for years but I don’t rock the checkers anymore and that’s ok. If you are in my demographic, you can wear Vans but they need to be the solid color Authentic’s or Era’s. The same thing with athletic sneakers, keep them low key, we are too old to be Sneaker Pimps. Lastly for the love of God, stay away from White New Balance sneakers, unless you are going to wear them with jean shorts, live in the Villages (huge retirement community in Central FL) and sport a MAGA hat.
There came a time when I tried to sport the big logo Ralph Lauren Polo’s. Huge mistake, unless you are Argintinean (and really play, think Latin Silver fox with a mustache) or a Narcotrafficante. Any logo’s should be small and understated. I don’t wear Ralph Lauren for the status, I wear it for the quality. I was wearing Polo oxfords from college in the 80’s all the way through the early 2000’s. As I type this, I am wearing a black Ralph Lauren tech polo I’ve had since early 2014 and it looks great. More on tech shirts in a bit. As far as other similar brands, Lacoste is great but the fit can be a little small in the wrong places. Vineyard Vines is great for the younger prep but in your 50’s you’re trying too hard (I do like Whales though).
I live in a warm climate so a lot of guys here wear tech shirts, usually with fish printed on them. That’s ok for some. My tech wear of choice is Patagonia or North Face. Columbia (who actually owns North Face) is great as well. These are adult brands. Again, wear them with pride for their quality and understated logos. I also wear a lot of LL Bean which checks the preppy box and the outdoor/tech box. However, big mistake a lot of guys make is wearing a button up fishing shirt in place of a dress shirt. Big no-no. I have a couple of nice LL Bean tech button downs that are a cool plaid. I wear them anywhere a polo or a tshirt would be appropriate but not with a sport coat or dress pants. I have a friend who wears Levis denim cowboy shirts, the really faded ones, with board shorts and somehow pulls it off, but its probably not a look for everyone.
By this age, you should know how to wear suit and if you have no suit game, I’m not sure I can help. My advice is to go custom. You can get a custom tailored suit for $1000.00. Owning 2 or 3 of these is much better than owning 5 or 6 suited separates. Stick with Blues, Greys and Subtle Plaids. In the South you can even go seersucker. Keep the lapels neutral because these suits last. I have one from 15 years ago that still looks great, I just need to have the pleats taken out of the pants and the legs tailored. A word on pleats, they come in and out of style (currently creeping back in) but they are not for all body types. Tall and slender yes, everyone one else, not so much. Use your ties and socks for creativity. As for your shoes, brown and black wingtips or cap toes for your base but maybe get a little crazy with some dress chukkas.
In Florida, where I live, it seems like a lot of older men revert to wearing Hawaiian or Aloha shirts as their go to. This is ok sometimes, especially if you are married and your wife doesn’t care. They look great down at the Elks club. I recently wore one of mine (purchased on my honeymoon in 2002) to an event and I liked it, except the sleeves were a bit long. Reyn Spooner (the Cadillac of Aloha Shirts) is now making them fitted with a button down collar, I may have to test drive one. Tommy Bahama is another popular brand with married guys. It shows up a lot in Facebook Posts of my male clients before their divorce when they were overweight, emasculated and miserable. They don’t wear them as much after the divorce when they have lost the weight and started getting laid again. In fact most of them dress like I have written above, understated, body specific, flattering and classic. Words to dress by.