Hello all, 

In the next couple of days I have a date with a fine young lady, and I ran into some questions about by dressing for the occasion. The date is very casual, it's in a part of town that has a lot of small sidewalk coffee shops, small but nice restaurants, all surrounding a nice park. It is a relatively upscale part of town, but has a very casual ambiance. I planne on wearing a nice pair of jeans, a collar shirt, a very casual sport coat (for all those handy pockets!) and have not decided between canvased sneakers or leather moccasins. My question is as follows, should I be tucking my shirt in? I feel like it is probably the best idea, but not sure how that plays into the "casualness." Take into account that I am young (17) and am trying to convey a sense of casualness without looking too untidy. Any suggestions/ideas/tips?

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I personally think what you have planned to wear is fine, shirt un tucked IMHO.

As just a nice pair of jeans and sport coat tends to make you look fairly decent already. Especially at 17 when most people are just 'jeans tshirt, whatever'.

I'd say you nailed it spot on.

Agreed.  I don't think a teenager needs to look too formal for a date.  What you have is fine.

You are definitely on the right track. Leaving your shirt untucked or tucked really depends on the shirt. Untucked might be more casual, but you can only pull it off with a fitted shirt that's not too long. It should definitely not be much longer than where your jeans end. When the length of the shirt even approaches the length of your jacket, you're in bad territory. 

Also, if your shirt is not fitted, untucked it will really 'uncomplement' your body. That, combined with a too lengthy shirt and the jacket will look like you're wearing two parts of 'over clothing'. The shirt should look and be 'smaller' than the jacket. 

I hope that answers your question. If you want i could take pictures to show what i mean. 

As for the shoes: go for leather. Moccasins are really casual, but convey a sense of style and panache. When wearing moccasins, make sure your pants are not too long, or they will soon look like house-slippers. 

Have fun on your date!

You'll want to be careful with an untucked shirt and jacket combo. If you are going to do that the shirt can't be too long and both the jacket and shirt must fit very well as was already mentioned. Otherwise it will just look sloppy and no casual. While I would probably go for leather moccasins or loafers myself I might suggest canvas sneakers, especially white or a bright colour, paired with the jeans (nice dark wash). 

Depending on the sport coat you are wearing you can also always do a well-fitted, high-quality t-shirt (I prefer a v-neck) underneath the jacket instead of a button down. This can also look very well put together and yet is still nice and casual.

Above all be comfortable and make the look yours. That is the most important thing, not which individual bits and pieces you are putting together.

I find the issue of whether to tuck a shirt into jeans to be tricky. It depends on the jeans, I guess. And the shirt. I find, a lot of the time, that it can clash. That's probably because I associate tucked-in shirts with more formal situations and jeans with more casual situations.

That doesn't mean it can't work, though. I've done it before and I'll do it again. As I said, it all (well, mostly) depends on the jeans.

The jeans might also have an effect on which shoes to wear.

I don't know how helpful this is. I guess my point is that just knowing a theoretical principal of what should look good won't always translate into an actually well put-together outfit. While guidelines can help, it's important to look at oneself in the mirror and not simply think "This looks good because I followed rules A, B, and C".

Also, how'd the date go?

the date went very well, thank you all for the advice Im seeing her for a 3rd this friday. =) The first went well in itself, the usual light conversation and what not. for the second we went to the movies, and had ice cream (a little unoriginal, but its a classic for a reason) and Friday Im taking her to a party that some friends are organizing. 

How will you introduce her to your friends? [rhetorical question, but be sure of the answer yourself]

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