I have discussed dressing age-appropriately, but most of the time, it’s regarding older guys trying to dress too young. Dressing young makes them look super weird and awkward. It looks like they’re trying too hard.
But on the flip side, you can also dress too old. I would like to discuss what makes you look like an old man. All the items I will cover make you look like a dad or a grandpa. You should never wear these to look like a young and stylish dude.
Don’t look like your dad — or grandpa!
- Ankle socks. Ankle socks with a band will likely be worn with unstylish shoes like boat shoes.
- Boat shoes. They suck!
- Athletic shoes. You should not wear athletic footwear or running shoes in an unathletic environment. You will look like you’re wearing old dad sneakers. You see them — big and bulky New Balance sneakers like Dads wear. They’re not stylish.
- Comfort dress shoes. These are the mullets of shoes, like those from Cole Haan. The top may be a brogued Oxford that’s leather with an athletic soul on the bottom. They are definitely not stylish.
- Mandels. The strappy sandals that you’ll see old dudes wearing.
- Blazers with metal buttons. Nothing more than a metal button blazer will make you look like an old dude. My favorite blazers come from Collars and Co. and have a lot of stretch and a slim fit.
- Baggy suit jackets. Any jacket that’s too big and baggy will make you look old. Wear a jacket that fits your body.
- Old man polos. Whether striped or have weird patterns, they are not stylish, even though they may be fun and functional. Instead, try a Collars and Co. polo with a nice collar that can be dressed up or down. It’s not striped like a little boy’s polo or with weird patterns like Grandpa’s. It also doesn’t have a country club logo on the chest.
- Dad jeans. These will be pulled up high and be a bit baggy. They have a regular rise and are very relaxed. These are horrible.
- Jorts. Long jean shorts (jorts) are usually worn with an ugly T-shirt and a fanny pack. These are usually paired with athletic or casual footwear for running around Disney World. Don’t do it!
- Baggy cargo shorts. These will automatically make you look like an old man because of all the storage pockets (and the stuff you put in them).
- Costco clothing. Sure, sometimes you can get some deals on nice items, but the truth is that most of them will make you look like a dad.
- Big and baggy pants hiked up. Any big, baggy pants pulled up too high will make you look good, dork. You want to ensure your pants have their appropriate rise and are not too long. If they’re too long, your legs will look super short. You want to ensure that you’re not getting a bunch of fabric when you reach down. Your pants should also not be puddling at your ankles. Have your pants tailored so you do not have big and wide legs.
- Pleated khakis. Younger dudes can sometimes pull off wearing pleated khakis, but for most of us, a much better option is flat-front pants.
- Baggy suits. Old dudes wear big baggie suits. Make sure you have your clothing tailored.
- Matching pocket square and tie. Make sure they do not match. The classic old dude wears a pocket square and tie that came in a set from his kids.
- Fun clothing. They are not stylish, whether it’s fun ties, fun socks, or fun t-shirts. They are old.
- Tighty whities. These are not stylish and will make you look like an old man. If you don’t believe me, go to a locker room in a gym.
