"Stylish" looks or clothes that you hate

[ianr]

The best OTR shirts I've found for untucking-optional wear are Ledbury shortened-body casual shirts. I fully embrace that look. They are supposed to be wrinkled and they are supposed to look "relaxed"; it is the whole point.

I have a difficult time with regular dress shirts with jeans untucked like Tim Cook. However, I've never heard anyone say Tim Cook is stylish.

I think it is like wearing a tie loose on purpose versus wearing a tie loose because it's 5:01 pm.

[dpark]

I think it is like wearing a tie loose on purpose versus wearing a tie loose because it's 5:01 pm.

Sorry, which one is the untucked casual shirt in this scenario? If you're wearing your shirt untucked because you prefer the style, it seems analogous to wearing the tie loose on purpose. Regardless of whether you're wearing a shirt that looks flattering this way.

[ianr]

Sorry, which one is the untucked casual shirt in this scenario? If you're wearing your shirt untucked because you prefer the style, it seems analogous to wearing the tie loose on purpose. Regardless of whether you're wearing a shirt that looks flattering this way.

Yes, that is what I mean. Tie loose on purpose is like shirt untucked for style preference. I can get down with both of those things. I like to think I can spot the difference, but I probably can't.

[Raakish]

Turtlenecks--sweaters or shirts. Quite trendy now. They look good on some guys, but not on me.

And they feel very confining. I don't like material almost all the way up to my chin unless I'm outside in very cold weather and wearing a scarf or high collar on my coat.

[proteus]

1. Turtlenecks --> too hot and no option to remove the neck part
2. Ascot --> douche bag
3. Man bag/purse --> doesn't need a comment, I rather wear a fanny pack
4. Birkenstock --> just never thought it was that stylish

[Paddington]

I agree with [MENTION=14764]dpark[/MENTION] on this: casual shirts tucked in do not look any nicer.

If it's a casual, soft wash shirt, it looks fine untucked. If it's a dress shirt, it doesn't. I think the line between casual shirt and dress shirt is pretty defined, but I'm sure others disagree. Even websites like J Crew and BR separate the shirts out this way. Tucking in a casual shirt is like tucking in a t-shirt to me; it seems pointless. If I was trying to dress nice enough to tuck my shirt in, I would be wearing a nicer shirt.

I dislike untucked shirts with blazers. I also dislike casual shirts with blazers. If you're taking the extra step to wear a blazer, wear a tucked in dress shirt to complete the look.