How To Dress Casually as a Grown Man | Fashion Over 40
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When I was a child I dressed like Opy in the Andy Griffith Show. When I was about 40 I looked in the mirror and saw that I dressed much the same; a T-shirt, blue jeans, and sneakers. I started to dress like an adult by first wearing my father’s hand-me-downs. I began getting compliments.
I do want to see more videos on this subject. I want to know things like, Are polyester golf shirts acceptable as casual wear, or should they be limited to the golf course? Are man-made fabrics okay or should I stay with natural fabrics? Do tennis shoes look good on men over 60?
Keep them coming the advice is welcome.
I live in Chicago and work in the trades so I’m always wearing jeans, work boots and T-Shirts. I do like to dress up a bit when I’m not working, this video is very helpful! Thank you Sir!!!!!
Result of gym attendance showing…. Keep it up
Your recommendation on Crocs?
I wear a lot of tee shirts where i live in Bangkok. Pergect for the weather there. Im still in shaoe at 67 . I wear Paul Smith tee shirts.
Thanks for all the helpful videos, John. I’ve added some suspenders to my wardrobe lately. I really like wearing them with jeans + an oxford shirt or jeans + a knitted polo shirt. I find suspenders to be more comfortable and stylish than belts. It would be interesting if you could make a video about this someday.
Thank you for calling out flip flops. If you’re by the pool, fine. Anywhere else. No.
Just wearing a good polo shirt jeans and good shoes can elevate you against the mass of men wearing ill fitting mismatched clothes
I always felt that combining the outfit of the day was hard. Then I got myself jeans, chinos and belts in different colors. Suddenly it became much easier to combine an outfit to match the season, weather and activity. Having options and a wardrobe mostly in the neutral color palette that John often talks about has made it easy and fun to choose outfit.
This channel has been amazingly helpful in helping me "grow up" in a way, as someone who got a little too casual over the pandemic. I’m tossing a lot of old concert and sports tees and trying to focus on nice polos (at least for the summer… I’ll have to figure out how to navigate a Canadian winter stylishly.)
I think my main hurdle now is with shoes. As someone who has had multiple ankle and knee surgeries, I lean towards ugly comfort (like a HOKA shoe) over something stylish. I wore nice suede shoes to a wedding this summer and was in agony the whole day. Not sure where to go in my case there.
On Jeans. If they’re too long, you don’t really have to get them shortened. IMO cuffing them is perfectly appropriate for high quality jeans.
You pretty much nailed it John. Not 40 yet but I am slowly approaching it as I’m currently in my middle 30’s so the videos are truly helpful. OCBDS, Long sleeve Linens, Basic Dress shirts, sweaters, slacks, and Chinos are all part of my wardrobe. I’m growing a little out of the jeans as I get older but I still keep 2 pairs around.
When I was younger, most of the guys who wore polo shirts were the preppy kids who did that pin wheel ankle roll with their pants and a sweater tied over the shoulders, or their polo shirt was tucked into their shorts. Now whenever I see a man in a polo shirt I just know he either plays golf, has played golf, or is getting back into golf.
Know I’m “old” at 71 but think it started with Casual Friday years ago and it got out of hand which humans will do. Saw a kid going into 10th grade this year wearing T shirt and shorts. The teachers look the same. There is a reason military and law enforcement wear uniforms. People get lazy. Wife compliments all the time about how “put together “ she looks. The bar is not high but most people sinking to the lowest level as people do. I dress so my spouse can be proud to be seen with me too.
Overhere white shoes (used to be called tennis shoes) are only worn by wimps that want to radiate that they don’t do physical work (blue colar here means brown or black shoes).
While I agree about graphic Tshirts for the most part, there’s nothing wrong with rocking a rock and roll shirt if under a nice black denim or leather jacket for a show or casual weekend trip out with your fine lady. Like anything especially when you get older, you’ve just got to know how to do it right! Great video
Those C&C polo’s are nice but they’re out in my size…try again later
Great piece
I admire this gentleman having to say the same thing over and over again to men all year long. It’s not that hard to dress for your age, and it’s not that hard to find quality stuff that matches. When I started my journey to dress better, I started asking chicks to come shopping with me. They upped my game big time, and now I just know what works and what looks amazing anytime anywhere. Many women, especially those that just want to be your friend, will be more than happy to help. #lmao
I wish people would pay attention to what they wear. Have you been to an airport or a Walmart lately?
People go out dressed in their pajamas or at best like they are going to a backyard BBQ! Most don’t even bathe regularly!
They put on clothes they get out of the hamper.
You live in California and are from Seattle so maybe those in your circle dress a little better there.
Go the to Midwest, Texas, Arizona, Utah, Montana or the south and take in the fashion there!
John, don’t you think a solid T-shirt can look good under a nice unzipped bomber or leather jacket?
Elevated casual FTW! I’m with you on that – Great video John!!! 👊🏻
I’ve been watching your videos for a while. I generally agree with you on most things, though I do tend towards more classically stylish looks. This video however was very generic and just seemed to be a way to get your sponsor money
Ease up on the word super.
what’s your opinion on wearing pants one length short. For example, I’m a natural 34/32, but I’ve been loving 34/30, because it doesn’t crumple the bottom of the pant leg on the shoe. It also allows the pant to hug the calf, which is one of my better features (thanks to years of athletics). Now, I look for *casual* pants (khakis, chinos, jeans, etc) one length shorter.
The old guys who tuck t-shirts into shorts and worn with a belt. Why ?
I recall from another fashion tips video you commented on men who give up and how it shows in the way they dress. I can’t stop seeing that concept where I live in Montana. Casual is considered dressed up here: anything beyond that means some life event or court! But so many fashion faux pas here. Like anywhere, there are exceptions. I purchased a pair of canvas, lace up sneakers in muted olive tone recently and they look more casual and even relaxed. The color does go well with some of my combinations. I have to agree about the Hey Dude brand-way too "popular" here and I refuse to purchase them. Another is Hoka: for therapeutic reasons, I get it, but everyday? Again, no. Always great advice John. I think a regional style advice video might be good: New England, Southwest, Pacific Northwest, and so on.
Thanks, John, for the sport coat idea recently added to wardrobe, three colors, navy, tan and blue .. immediately sets off everything and better dressed right off the bat. Been tough to do during the heat waves, but for most of the year it’s a winner.
I try to follow the “style rules”, and dress my age, but I must admit, dressing was way more FUN, when I was a young man. In my opinion, following the “rules” doesn’t leave much room to stand out…but I follow them anyway.
I think it is ok to wear flip flops and the similar during certain instances outside of the pool / beach.
A thoughtful piece. Well done.
Great Advice…. I appreciate you! Always so positive, real and uplifting. Keep it up!
These are all great tips and completely agree. I do however, have a hard time. I’m 55 and 305 lbs. I’m working hard to reduce, but in the meantime, I don’t want to look like a schlub. It seems that all of the extra weight is in my stomach. So when I buy a 3x (to fit my stomach) it’s too big everywhere else. When I buy a 2x, it’s too small. I’ve found 2XB in stores like Kohls, and websites like DXL, and KIngSize, but choices are limited and so is style everything seems to be extra long, or they have cargo shorts and pleated pants etc. It gets frustrating. I checked Collars and Co and they only go up to a 2x as much as I like their stuff it won’t fit, sadly. I wish that some of the men’s channels on here would do some videos for larger guys…I know there’s stuff out there, I just can’t find it.
I live in Western Australia, so it’s too hot to wear a jacket 6 months of the year. Blokes here are generally terrible at dressing themselves, with board shorts and scruffy t shirts with flip flops the uniform of many (often barefoot, even in places like supermarkets). My girlfriend of 8 years assumed I was gay when she met me, simply because I was dressed in a polo shirt, cream chinos, and loafers. That’s how low the dress sense ‘bar’ is here.
My cooler weather uniform tends to be dark wash jeans or chinos, Chelsea boots or Adidas Originals (usually Gazelles or Spezials), a plain shirt (no patterns) or polo shirt, and a lightweight jacket. In hot weather I wear a lot of linen blends, and yes my iron gets used a LOT. I know you said the t shirt is low on the totem, but a slim fitting plain black t shirt is one of the coolest and most flattering items you can wear.
Living in Bangkok , most guys wear sandals and shorts.
John, you can sell just about anything. I like that you emphasize classing up what one’s personal style. you have been a huge, positive influence on my clothing choices. I always say to myself, "What would John say/think?" thank you!
Great stuff. I sell wine in a very upscale spirits store, and we do wear polo shirts for work. I just try to do the best with what I have to work with, but my clothes fit well, and I put a lot of time into grooming. Sadly, a lot of our customers can’t say the same, most show up dressed like bums. We do get some sharp looking guys, mostly military or retired military I think.
John on of the reasons I do not like polos us that most of them are short sleeve. I am a fit guy but do not like exposed arms. Any ideas on long sleeved polls?
I don’t like polo shirts. I Don’t buy them or have them in my wardrobe. I’ll pass on the polo shirts.
After going self employed and working from home I have not worn a suit in 18 years (except one funeral) plus we moved to Southern Spain at the same time which is class less either by money or dress code. You can dress up or down for dinner no one cares, it is still strange see one table all smart and another group in shorts and flip flops. I tend to wear shorts and linen shirts in summer and jeans and t shirts / long sleeve tops in winter (rare to drop below 10c in the day) I do think my causel style is two fingers up (UK) one finger up (US) towards my corprate life of three peice suits, braces, pocket square, shirt and tie etc etc. In the 18 years of leaving the UK I think I have clean shaved about four times. I call my style Boho chic ……………….. well thats what my wife says. Great video and keep up the great work.
I live in boots of one sort or another, seven days a week. Can i pair a polo with boots or is that going to look off?
Gym shorts and T-shirt and ball cap are not cool in a mid scale to upscale restaurant. $30-100 plate .
Crocs!!!! I find them repulsive.
I don’t dress up if I’m running errands but I dress decent if I’m going to church, restaurant, casual party
No graphics tees (cartoon characters etc) Spider-Man is the dude, but only 10 year olds will compliment your shirt….
If your shirt doesn’t have a collar, you’re in the gym or you’re a man-baby
Great photo. I am one for the KISS system #Legend
YES, finally. 🎉 T-shirt is pajama!!
Only looks good on fit young guys. Men dressing like toddlers… 🤦♂️🤦♂️ (including myself not long ago, anyone can change 😎)
I will say, one situation where I think walking shoes or athletic shoes are appropriate as if you’re literally going to be walking around all day, such as taking the family to Disneyland. Trust me – in situations like that, function over form is probably the way to go lol. But even then, you don’t have to look like a slouch. You can wear a pair of casual chinos and a comfy polo, for example
What are the best shopping options for big and tall? Shoppimg is a miserable experience because nothing fits. Im 6’5", long torso, long arms, wide shoulders with some extra weight. Where can i find clothes that fit? Pants are hard to find, too.
Your videos have helped my husband find his style and he is loving the compliments he receives. Can you link the suede loafers, please?
Please get more specific