Right, so I've scored myself a date with my childhood best friend and - as you can imagine - I'm looking for advice. I'm only willing to wear boat shoes, brogues or converse depending on the location. It may be a 50's diner we've wanted to go to, or it may be a trip to London. Please bear in mind I will not be wearing wool/tweed. Suggestions would be appreciated.
Firstly, it depends completely on where you go.
If you take a trip to London you will have to accommodate for the weather. It is has been very warm these past few days, and the last thing you want to do is wear a nice shirt and jumper and end up sweating profusely on the tube.
I would suggest a pair of brogue's, jeans (slim/skinny indigo) and a shirt would suit most occasions. A classic stone-coloured Harrington jacket would work very well over the top, and it is always easy to sling into a bag if you are too hot.
A pair of minimalist white leather trainers (not sure what your converse's are like), no socks; with a grey t-shirt or pattern shirt and light-washed jeans would also look pretty good.
Considering you are aiming to impress her, I would have thought you had already done that throughout the years you have known her and thus she really won't care about your wardrobe.
I don't own half of that I'm ashamed to say...
Women are bloodsucking, heartless, fickle and cruel.
Right, now that I've got that bitter exclamation out of the way following my recent breakup, let's move onto your outfit.
Brogues are always a good shout, as it's been scientifically proven that they make the fairer sex go weak at the knees. Pair them, as Ben said, with a pair of slim dark wash indigo jeans.
As for the top half, keep things casual but well but together. A blue or white oxford/chambray shirt is always a safe option. Jacketwise, I like the idea of the harrington. My personal style leans more towards the smarter side of the spectrum, so I'd personally opt for a light summer trench, maybe a short cut one like Zara and Reiss have both offered this season. A well fitted black leather bomber jacket would do the trick if you're seeking a bit more of an edge.
If the weather allows, you could actually forget the coat altogether and opt for some knitwear instead. A lightweight, fine-knit merino cardigan or v-neck would compliment the shirt nicely.
Keep things neat, clean-cut and refined. Don't think about it too much, women can smell it from a mile. I try far too hard, which is probably why I'm a disaster regarding girls.
Leather jacket on the tube in this weather = human microwave.
They are so beautiful, but tube's are their kryptonite. If you go to London and wear a leather jacket, avoid the tubes if it is hot!
Nathan's suggestions are great. At the end of the day, you are 14 and thus any attempt at wearing brogue's or something sharp is great (sorry if this sounds pretentious or condescending). When I was 14 I was wearing skinny levis and Abercrombie and Fitch polos and hoodies. It is a great age to explore different trends and not look like an idiot (potentially an overdressed nonce, but rather that than an underdressed tramp).
To be perfectly honest I'd rather be perceived as someone who "overdresses" than someone who underdresses - snapbacks, Nike Air Max and the hoodie that's undone with the strings tied in a bow. Thanks for the suggestions guys, I had a feeling brogues and slim jeanswould be a popular choice so I'll definately go with that. Where could I get a nice looking, decent quality harrington for under say £55?
I'd have a look on ASOS mate. If there's nothing there that floats your boat, alot of vintage shops sell some nice, retro pieces.