If you are serious and its important to you, its not weird. If it helps you feel more comfortable at the new stable to dress up then go for it. On a daily basis I don't dress up much around the horses or to ride, but there is not really anyone around to see me at home :) I have a range of everyday jodhpurs in bright colours and more traditional and just wear t shirts/sweatshirts or singlet vests when its extra hot. When I go to show clinic or other group lessons I guess I dress up a bit more,wear a nice shirt, tucked in, with breeches and belt, so this us probably the type of style you are aiming for.
HELMET:
I have one like this as my everyday helmet
http://www.horsesrus.com.au/products/jodz-deluxe-safety-helmet.html.
BOOTS/CHAPS
- definitely leather half chaps, or tall boots, but I much prefer half chaps and they look very nice. My everyday wear is ariat paddock boots and chaps like these
http://www.ariat.com/products_detail.aspx?pcid=8&cid=1&scid=11&pid=844
More dressed up than suede chaps.
BREECHES.
- just nice quality, plain colours, tan, beige, cream, white, black, grey, hunter green. Or subtle patterns (like pinstripe or plaid, with suede patches) with a belt, leather to match whatever colour you boots are. Beige/tan, creme are a good basic pair to have though. I love my white breeches, but they are sooooo not practical. But the look pretty :)
SHIRT
- I would never wear a ratcatcher show shirt for everyday, Not comfortable! and would be too hot for about 80% of the year here. A nice, long sleeved or 3 quarter length sleeved, plain coloured, firm fitting shirt tucked in looks just as nice (go navy, grey, black or the like. I love the look of white breeches with a navy shirt. Or tan breeches with a black or navy shirt. Or casual show shirt like this
http://www.smartpakequine.com/productclass.aspx?productClassid=7481
Or a nice simple polo shirt, tucked in looks very nice for schooling and everyday.
EXTRAS
- gloves finish off the picture nicely.
- braid your hair and tuck under your helmet
Just some examples, simple but classic and nice looking
http://i587.photobucket.com/albums/ss318/soph_h/pony%20randoms%204/169957.jpg
http://i587.photobucket.com/albums/ss318/soph_h/outfit1.jpg
http://s587.photobucket.com/albums/ss318/soph_h/?action=view¤t=outfit4.jpg
http://s587.photobucket.com/albums/ss318/soph_h/?action=view¤t=outfit2.jpg