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5 Clothing Items All Men Should Ditch Once They Turn 40

Prime Parents Club Fashion Men Over 40As a busy family man with two kids, keeping up with fashion is rarely high up on my priority list. I usually wear whatever happens to be in the closet and barely look in the mirror before I leave the house in the morning.

However, after a recent outing to the movies with my kids, they told me they were embarrassed by my clothing. My Metallica t-shirt that I’ve had since the 90’s with my acid wash jeans weren’t up to scratch–according to them–and they strongly advised that I update my look. Although this was somewhat of a blow to my ego, I realized they were right. My current look was more than a little dated.

As my 40th birthday approached, I decided it was time I changed my look. I began to throw out much of my very dated wardrobe and replaced many items with more age appropriate attire. This recent experience made me notice that I am not alone in having fashion shortcomings. A lot of other men my age wear ridiculously age inappropriate clothes and rather than looking on trend they usually just look plain silly.

5 clothing items that men over age 40 should avoid wearing all costs

1. Speedos

Not wearing Speedos over 40 may sound like a given, but you’d be surprised how many men over 40 still try to pull this look off on the beach – seemingly oblivious to their often-times horrendous beer guts. Unless you are planning on vacationing in Brazil any time soon, avoid this look like the plague.

2. Wife-Beaters

That beloved sleeveless vest may have looked great when you were 25 and had bulging triceps, but now that you’re 40, a wife-beater will likely just make you look out of shape (think Tony Soprano) and probably a little creepy to boot. Trash this look and try sleeved t-shirts instead.

3. Humorous T-Shirts

That “I’m with stupid” t-shirt may have been a great icebreaker a decade ago, but it probably doesn’t get a lot of laughs today. Act your age and avoid humor t-shirts once you reach the big four-oh. This doesn’t mean you can’t still crack jokes and be the life and soul of the party, it’s just generally a good idea to avoid branding jokes across your chest once you get past puberty.

4. Vintage Clothes

Vintage clothes can look very chic on the young and hip, but once you arrive at the borders of middle agedom vintage apparel will likely make you look like a walking museum. Don’t waste your money on expensive vintage gear that reminds you of your lost youth and definitely throw out any clothes your mother bought you when you were still in high school. Try and wear new, fresh clothes that are age and era appropriate.

5. Tennis Shoes

Tennis shoes are fine for the gym or the tennis court, but probably will make you look a little strange if paired with jeans or work pants once you get to 40. Swap your tennis shoes for sleek loafers or smart dress shoes. You don’t have to throw out your beloved sneakers or tennis shoes, just wear them in moderation and only for appropriate sports themed occasions.


As you can see, there are multiple looks and pieces of clothing that just aren’t going to work once you turn 40. What once may have been your best look has the potential to make you look odd and older than you are as you enter your fourth decade. You can still embrace fashion, but just remember to dress your age. Good luck!

Duncan King is a freelance writer and divides his time between visiting his kids at their New Hampshire Boarding School and working on his upcoming crime novel.

This post was written by a guest writer for Prime Parents Club. We are not currently taking new guest writers.


  1. Another Mike

    July 7, 2016 at 3:04 pm

    This listing is fine as a “rule of thumb” but there are exceptions to every rule. If a man still has a HOT body after 40 he can probably get away with wearing a speedo but not the extremely skimpy/thong types. Square cut or the mid waist type. Wifebeaters around the house or doing yard work but once again, if you’ve still got the “gym” body, you can probably get away with it. NO to the humorous t-shirts esp. the big lettered, neon colored ones. If the saying or the picture are subtle and humorous then depending on the humor, you may get away with it. Vintage clothes, once again, depends on how they are put together. A zoot suit or 70 disco outfits – NO but a chic pair of vintage slacks, sports jacket, shirt can look great but needs to be carefully planned out. Tennis shoes – don’t see a problem unless they’re neon or trendy. Classics will win every time. My opinion!

  2. franz

    July 1, 2013 at 1:45 am

    I disagree with the tennis shoes. God if I now have to wear penny loafers and slip on shoes please shoot me like a wounded hoarse now.

  3. Dave McGoldrick

    May 30, 2012 at 7:44 pm

    While my teenage daughters wish I dressed like their dad, I feel as though I should have the right to dress the age I feel, which is probably 17 again. I’m a little over 40 and humorous t-shirts to me are pretty cool. I’m awful at shopping myself and I guess I just tend to buy anything from anywhere without any real thought. My wife did some online shopping for me on and I have to say their clothes are pretty good, smart casual but I still tend to wear my ‘tennis shoes’ and humorous t-shirts over smart casual wear most days. I guess I should just dress my age…

  4. Robb J

    February 10, 2012 at 7:19 am

    As a male over 40, I have to take a little exception to your ‘suggestions’. I totally agree on the white tank top and speedos. However, I wear tennis shoes on a regular basis. I also have a collection of ‘funny t-shirts’. I’m not quite sure what you are meaning regarding vintage clothing? If its bell bottom trousers or a velour jump suit, ok. But some vintage clothing, if properly put together, can look nice.
    Maybe I’m just a backwards, soon to be 42 yr old, stuck in the mid-west. But I dress for comfort and what wear what I like. I’m not here to be a fashion show for the ladies or to land a gig as a Eddie Bauer model.

  5. Christin

    February 9, 2012 at 12:26 pm

    While I wish my Prime hubby would read this and comply, he feels that he is so “prime” (as in still hot) that there is no need to worry what others think about his fashion. :-/

  6. Tina

    February 8, 2012 at 1:57 pm

    I asked My 20 year old son his opinion and he said after your 40 you should wear “gap” or “express”. I had to laugh at that! This bums me out a bit because I was also told women over 30 should no longer wear torn up jeans. I’m a creature of habit. I love my Poison jeans. Speedos and wife beaters are always a no, unless your Kid Rock then wife beaters are a MUST! My husband would be sad to read this because he loves his funny t shirts and tennis shoes. And vintage is hot if you still have the body for it! I think wear it if you can still rock it!

    • Prime Parents Club

      February 8, 2012 at 2:18 pm

      I’m okay w/”prime Parents” wearing torn jeans. I think they’re cool. But, I guess it depends on where you are wearing those “tears.”


  7. Steven Depolo

    February 8, 2012 at 11:41 am

    Nothing worse than an old guy in a team jacket, baseball cap, stonewashed jeans, and white Reebok cross-trainers. You, sir, are an adult. Dress like it

  8. Prime Parents Club

    February 8, 2012 at 8:18 am

    Not sure I agree. YES, ditch the Speedos..ALWAYS. But I’ve seen some pretty put-together 40+ men in vintage clothing and tennis shoes. Might be a miss on that. If you where them like you’re 40 and not a 40 year old man trying to be 20, I think some can pull it off.


    • Prime Parents Club

      February 8, 2012 at 12:21 pm

      *Wear not where LOL

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