One fashion mistake IMO is trying to look serious all the time or being grouchy. “A smile is an instant face lift.” Forgot who said it, but it is so true. We are not talking teeth-out grins. A Mona Lisa kind of slight smile instantly makes one look younger. 
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My husbands wardrobe is identical but in a different college theme. Oh! He does have a baseball theme also.
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DH has a few Patriots shirts in there, too.
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Improving my husband’s fashion has been on my “to do” list for at least the past 25 years. He is a very successful business owner, super intelligent, yet his daily “fit” consists of horribly bunched-up, wrinkled cargo shorts and a faded company logo polo, that usually has at least one food-related stain on it 
Oh, and the old guy white sneakers - can’t forget about those! The kids tease him incessantly about his sneakers (he proudly buys 3 pairs a year from Kohls!)
The one exception is when we go on vacation - he has his vacation outfits, and while they are a step up from his usual, it’s not like we can incorporate palm tree shirts and white shorts into his daily rotation.
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D2 recently said to me, “I am beginning to appreciate Mommy’s looks. Can I borrow few of your dresses?” I didn’t know whether to take it as a compliment (am I dressing too young?).
I wear a lot of loose linen dresses in the summer. I don’t like pants because they feel too hot against my skin. In the winter it is boxy cashmere sweaters and skinny pants with ballet flats or boots. I tend to go with solid colors except when I am on a beach vacation.
I do get dressed up when I go out, especially now I live in NYC. After 6pm at many restaurants people are generally dressed. I recently went to a very nice restaurant with a friend without a reservation. We were dressed with appropriate accessories. They gave us a very nice table at a bar and then move us to a corner table for dinner (with the stipulation that we had to be out in 2hours ).
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We recently were preparing for a trip to Ireland and Scotland and my husband was packing his ten year old Adidas three striped soccer pants. I told him nope, you’ll look like a Russian gangster. I showed him all the soccer pant memes online and he finally packed some other sweats, which he never wore thank goodness.
Every time he saw someone wearing soccer pants, he’d point them out to me, but then I pointed out to him that none of the wearers were over 30 years old.
Example meme
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I’m happy to report that my D and I finally convinced my H that he was dressing like it was still 1980 and that baggy, ill fitting clothes just made him look like he was a kid wearing his dad’s clothing. Over the last 5 years we’ve totally managed to turn over his wardrobe. This year the man finally agreed to his first custom made suit (after we fought that he had nothing appropriate to wear to my parents’ memorial service).
He’s now hooked on well fitting clothes but now he spends more than I do ; )
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My husband has always been very fashionable and he spends way more than me on clothes and shoes. I am very frugal and always looking for sales and he is of the mindset you have to buy it when you see it.
Hah. My H always wanted long hair, so now he has a silver ponytail hanging halfway down his back. It actually looks nice, but the beard/sideburns/mustache should have been shaved off 30 years ago. But it’s his body, and I love him no matter what. His casual wardrobe is fine when he leaves the house … he is constantly working around the house, so when he’s home, he tends to wear ratty old gym shorts or jeans & t’s that have seen better days. He recently bought a very nice suit & shirt and had them professionally tailored. We went to a wedding, and not only did he look great, but he felt great. He wants to kick up his wardrobe a notch now.
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My husband has been wearing the same “uniform” for the last 25 years - summer - beige cargo shorts with a blue polo shirt, winter - jeans with a plaid flannel shirt. Yes, he buys these same items year after year.
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My husband buys his own clothes when we go to England, so he gets his resupply every year.
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I consider it a win if I can get my husband to stop tucking in his t-shirts.
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Cargo shorts on men should be outlawed over the age of 15.
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Late to the fun. I think this was mentioned, but jewelry is instantly aging. Matching necklace, earrings, bracelet. That’s old. Too much jewelry….old. Statement necklaces are old right now. They’ll be back in fashion…just not right now.
Shorts that are less than 4” inseam.
I agree with several original OP “old” items.
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I’ve told my husband he needs a vacation wardrobe re-do. He’s had the same shorts for 20+ years, and he thinks one pocket colored t-shirts are fine for dinner, or his “dress” sweatpants (ha ha). I would be fine with the shorts if he’d put on a polo like shirt, as an option, or a button front casual shirt. He has lulu ABC pants, and those are a fine option.
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Not that I’m any kind of fashionista, but here’s some of my outfits for those looking to update their H’s wardrobe. I always focus on stretch, comfort, and lightweight (I live in AZ). About 4 years ago I switched from a company where the average age was probably 40-60, to one that’s more 21-40. My first day in the office I realized I was dressed like the old guy! So I ended up revamping my wardrobe with many of the staples below.
The Luxe Sport line are lightweight, super stretchy and comfy jeans. The only jeans I could tolerate for those 5am - midnight long business days including plane rides. I wear the Slimmy but you can pick a style that matches his body shape. Wait for a sale or check Nordstrom Rack.
Lightweight stretchy, comfy shorts for dinner out on hot summer nights or general running around when you want to look decent.
https://www.nordstrom.com/s/travismathew-starnes-stretch-performance-shorts/5263818?origin=keywordsearch-personalizedsort&breadcrumb=Home%2FAll%20Results&color=001
If you absolutely must have cargo shorts. These have a little bit of stretch but not a ton.
Lightweight super stretchy short sleeve shirts for summer nights out.
https://www.mizzenandmain.com/collections/short-sleeves
Lightweight button down business casual shirts. The material actually has more stretch than many of my hoodies and workout gear. This brand is more fitted, so not the best for guys carrying a lot of extra weight in the middle.
https://www.mizzenandmain.com/collections/dress-shirts
Dressier night-out shirts, more of a traditional cotton feel but with some stretch (not as much as the Mizzen & Main shirts though).
Casual, comfortable slip-on shoes that look a touch better than sneakers. Lightweight and mesh upper so you can go sockless or wear no-show socks.
Still casual, but sometimes you want a leather upper.
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Very nice. My husband is a big fan of those Tommy Bahama cargo shorts because he can keep his car fob in the side pocket (which does label him as an old guy - he prefers walking up to an automatically opened car instead of having to unlock the phone and push a few buttons to unlock the car like the youngsters do).
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I agree very nice choices. If I ever move jobs and need to wear “fanicer” clothing, then I might be a buyer.
I personally don’t wear cargo shorts, but the ones pictured look like they’re for skinnier legs than mine.
I really enjoy Vivo’s for casual and also athletic shoes.
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When D2 was in high school, her Dad decided he wanted to be more hip. He started to wear more chic sweat tops, tighter/ankle length pants and sneakers. Kids at her school told her that her Dad looked cool. She said to her Dad, “Can you just dress like all other dads.”
Thanks for posting - my DH has similar taste and does all his own clothes shopping. I will mention these brands. Comfort is key for him!
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