Turtleneck and button-up shirt?

I don't suppose it'll hurt, provided the turtleneck is some innocuous-looking color (like brown) that blends in easily with your skin tone and doesn't catch the viewer's eye more than it has to. Black might work. I suggest leaving the button-up open for the first two buttons.

I have a friend that does it all the time and it actually looks good. The thinner the turtleneck the better, as it'll look all tight and puffy if it's thick. I prefer to keep the colors somewhat distinct and contrasting, but not as to catch attention, as Alias suggested. A sky blue turtleneck, white button-up...or red turtleneck and charcoal button-up. And yeah...keep the top-2 buttons open.

I do not agree with you at all. The turtleneck can be rather thick. It looks really good anyway. It looks even more casual with a little thicker turtleneck but still elegant. I saw Gant using a sky blue turtleneck with a shirt that had a white base/bottom but a sky blue pattern and it looked smashing

In another post you mentioned that you were 16. Anyone else on here agree that the turtle neck, button up combo is going to make him look a little beyond his years, not to mention a little nerdy (sorry man)? I'm not sure what you style is, but this look seems kinda stuffy; save it for when your 35+.

I'd skip it at any age.

you're telling someone to dress a certain way in order to conform to the expectations of others. horrible advice. gqwannabe, wear whatever makes you feel comfortable and don't listen to anyone who tells you to dress your age. only you can decide where you are in life and what is appropriate for your age. when i was in high school, i wore dress pants and dress shirts to school because those were the clothes i liked. i went to a school where just about every guy wore a t-shirt, shorts, and sneakers everyday. i consider this being underdressed for just about anywhere unless you are playing basketball, tennis, etc... no one ever told me i should dress differently, and even my friends, who dressed like slobs, never said anything. when i was a freshman, there was a senior at school who wore a suit and tie everyday with sunglasses. i thought he looked cool, and if i were to go back in time and attend high school again, i'd dress the way i do now (suit w/out tie). be yourself - always.

Put on the combo and decide for yourself. Only you will know if the look reminds you of Grampa or a teen. As you mentioned, there's a time and place for everything and only you can judge. You posed the question and received the answers...now you decide. That's the beauty of style...that you decide. =]

Style is a personal expression. Personally, I think that the look is hard to pull off without looking a bit "tired". If the shirt is freshly pressed, too new or formal it will seem stiff and forced. As it will if you roll the turtleneck to neatly. This is not to say that it can't be done, but real style cannot be forced. Believe it or not, I think it is time for the "dickey" to be re-introduced. Currently, I am designing a line of high tech clothing that will include a modern version of this misunderstood and maligned garment. Thanks for giving me a chance to express my opinion. All the best, I am sincerely, Kyle. VintageKyle.

it's really a preppy look. some people can carry it off. towards that end, it has to do with color choices (pattern, details) and thickness. usually, though, it appears, as someone pointed out earlier, 'stuffy'. the mock (like 1/2 height of a 'true' turtleneck) works much better, imho.