No i never take it as far as suits heh. That would be pushing it WAY too far. I might wear a sports jacket if I was doing a master's or something, but you've gotta consider that most kids dress pretty badly. If i took it to the extreme of suits(which i wouldn't even consider doing really), I just don't think it would go over very well. I've got lots of opportunites to dress up (I eat out at nice restaurants a lot) so there's no reason for me to go overboard at school.
I really like the look you describe btw. I don't think it's "dressed-up", but then most kids probably would cause of the jacket... Although I like the look, I wouldn't wear it here... It would probably go over better at a school with lots of wealthy kids who have been brought up wearing school uniforms and who have been surrounded by well dressed men their whole lives.
Now to answer your question. I just wear nice pants (lots of armani, mostly collezioni but some black label too), usually wool, never with creases or pleats though, that's getting too dressy for the environment I'm wearing them in. Plus the absence of creases and pleats generally means the designer intends them as casual pants as well. I mean they still look pretty dressy by most standards, but they don't cross the line into carleton-land(which they would if they had pleats and creases imo).
For tops, I have lots of sweaters. Sweaters seem more casual than button-downs. They're relatively close fitting sweaters with some nice unique details you might not see every day on generic br stuff. I think knits would be more appropriate actually. When I think of sweaters, I can't help but conjure up images of the thick itchy things I was forced in to by my grandmother when i was really young  (i used to hate wool clothing). They're all at least merino quality wool (so that they're comfortable when there's nothing between them and my skin), pure cashmere and some cashmere/silk blends (85/15 cashmere/silk and silk/cashmere). I've got a couple of v-necks which i'll wear with a button-down underneath.
Hrm you know what, I just made a similar reply to a post on another forum so I'm gonna paste some stuff from it:
The pants in particular have some very cool fabrics that you won't find anywhere else. I've got around 10 pairs of pants from this label. They're mostly 100% wool, but I've also got linen pants and a pair that's a cotton/rayon blend. They all fit extremely well and like I said the fabrics are great and unlike anything you'll find from anyone else. They're very supple and they hang well. I like to keep things "casual" so none of my pants have creases and they're are all flat front.
I've also got a bunch of boss hugo boss pants(the armani pants are a looser fit in general). In terms of quality of construction and fabrics, they're not as good as armani, but they're not as expensive either. They look very sharp though.
For tops, I've got a couple of Zegna dress shirts which have been altered by my tailor. Altered means darts and getting rid of the extra material that you would normally tuck in to your pants. This doesn't work with every dress shirt (most dress shirts just don't look right w/o a sports jacket or suit) obviously but the ones I had altered are now 2 of my favorite casual shirts. One is a rich medium blue with a bit of a sheen to it that looks really sharp with a pair slim, dark charcoal, boss pants, and the other is a textured beige shirt that's looks great untucked with a pair of oliveish (closest i can describe the color) light wool pants (intended for summer). The beige shirt doesn't have darts (intentionally, I wanted it looser for a more casual summer look as opposed to the streamlined look i get wearing the other shirt), but i did have the tails and extra fabric at the bottom of the shirt removed so that it didn't look bad untucked. And you've just gotta love the double-thick mother-of-pearl buttons heh (i've gotten pretty sad really.. i can't buy a shirt anymore unless it's got nice thick mother-of-pearl buttons).
I've also got some crewneck shirts. I've got a 15milmil from zegna which is more shirt than sweater, even though it's wool. I've got a kind of olive rayon donna karan.. not dkny.. one of my favorite shirts, it looks jsut awesome with my beige linen pants. The way it drapes and ripples with a slight breeze is really cool heh.
For shoes, i've got a couple pairs of kenneth cole which i don't really wear anymore except in winter cause i don't mind trashing them (although my black pair is pretty nice) and I'm not gonna wear my beautiful calfskin ferragmos in the snow/slush... When it's not winter, I've got a 2 pairs of ferragamos: the first is a pair cognac colored slip-ons and the second is a pair of plain black slip-ons (i feel loafers are for older guys, but slip-ons are fine for guys my age). I've also got a pair of very light beige suede shoes by boss. They're not the best quality (when compared to something like ferragamo anyway) but they're really nice shoes and they get a lot of attention. i've had people ask to touch them heh.. they're a very fine suede (comparable to what you might find on a nice coat), not the like the more coarse suede you find on many shoes. I've got a very nice pair of leather sandals by burberry too. Oh i've got a pair of brown gucci loafers with a very tiny gold G on the tongue (and it is tiny, i wouldnt have bought them if it was a big G that screamed gucci heh cause that's tacky..)
Both of my coats are boss hugo boss. One is a charcoal wool 3/4 overcoat and the other is an insulated navy blue nylon number which has a really sharp silhouette (just a regular coat that falls to the waist and looks better unzipped than zipped).
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Anyway that's me from head to toe. If some stuff is repeated it's cause i pasted most of the post after I had already started with my reply. Oh and in terms of colors I wear a lot of shades of blue and grey, navy and black. In the warmer months, in addition to the blues, I've got all shades from beige/cream to olive (well not really olive but i suck at describing colors)
edit:just looked at post. grammar is really really bad heh. sry i was just kinda listing stuff and not paying much attention to it.
I really like the look you describe btw. I don't think it's "dressed-up", but then most kids probably would cause of the jacket... Although I like the look, I wouldn't wear it here... It would probably go over better at a school with lots of wealthy kids who have been brought up wearing school uniforms and who have been surrounded by well dressed men their whole lives.
Now to answer your question. I just wear nice pants (lots of armani, mostly collezioni but some black label too), usually wool, never with creases or pleats though, that's getting too dressy for the environment I'm wearing them in. Plus the absence of creases and pleats generally means the designer intends them as casual pants as well. I mean they still look pretty dressy by most standards, but they don't cross the line into carleton-land(which they would if they had pleats and creases imo).
For tops, I have lots of sweaters. Sweaters seem more casual than button-downs. They're relatively close fitting sweaters with some nice unique details you might not see every day on generic br stuff. I think knits would be more appropriate actually. When I think of sweaters, I can't help but conjure up images of the thick itchy things I was forced in to by my grandmother when i was really young  (i used to hate wool clothing). They're all at least merino quality wool (so that they're comfortable when there's nothing between them and my skin), pure cashmere and some cashmere/silk blends (85/15 cashmere/silk and silk/cashmere). I've got a couple of v-necks which i'll wear with a button-down underneath.
Hrm you know what, I just made a similar reply to a post on another forum so I'm gonna paste some stuff from it:
The pants in particular have some very cool fabrics that you won't find anywhere else. I've got around 10 pairs of pants from this label. They're mostly 100% wool, but I've also got linen pants and a pair that's a cotton/rayon blend. They all fit extremely well and like I said the fabrics are great and unlike anything you'll find from anyone else. They're very supple and they hang well. I like to keep things "casual" so none of my pants have creases and they're are all flat front.
I've also got a bunch of boss hugo boss pants(the armani pants are a looser fit in general). In terms of quality of construction and fabrics, they're not as good as armani, but they're not as expensive either. They look very sharp though.
For tops, I've got a couple of Zegna dress shirts which have been altered by my tailor. Altered means darts and getting rid of the extra material that you would normally tuck in to your pants. This doesn't work with every dress shirt (most dress shirts just don't look right w/o a sports jacket or suit) obviously but the ones I had altered are now 2 of my favorite casual shirts. One is a rich medium blue with a bit of a sheen to it that looks really sharp with a pair slim, dark charcoal, boss pants, and the other is a textured beige shirt that's looks great untucked with a pair of oliveish (closest i can describe the color) light wool pants (intended for summer). The beige shirt doesn't have darts (intentionally, I wanted it looser for a more casual summer look as opposed to the streamlined look i get wearing the other shirt), but i did have the tails and extra fabric at the bottom of the shirt removed so that it didn't look bad untucked. And you've just gotta love the double-thick mother-of-pearl buttons heh (i've gotten pretty sad really.. i can't buy a shirt anymore unless it's got nice thick mother-of-pearl buttons).
I've also got some crewneck shirts. I've got a 15milmil from zegna which is more shirt than sweater, even though it's wool. I've got a kind of olive rayon donna karan.. not dkny.. one of my favorite shirts, it looks jsut awesome with my beige linen pants. The way it drapes and ripples with a slight breeze is really cool heh.
For shoes, i've got a couple pairs of kenneth cole which i don't really wear anymore except in winter cause i don't mind trashing them (although my black pair is pretty nice) and I'm not gonna wear my beautiful calfskin ferragmos in the snow/slush... When it's not winter, I've got a 2 pairs of ferragamos: the first is a pair cognac colored slip-ons and the second is a pair of plain black slip-ons (i feel loafers are for older guys, but slip-ons are fine for guys my age). I've also got a pair of very light beige suede shoes by boss. They're not the best quality (when compared to something like ferragamo anyway) but they're really nice shoes and they get a lot of attention. i've had people ask to touch them heh.. they're a very fine suede (comparable to what you might find on a nice coat), not the like the more coarse suede you find on many shoes. I've got a very nice pair of leather sandals by burberry too. Oh i've got a pair of brown gucci loafers with a very tiny gold G on the tongue (and it is tiny, i wouldnt have bought them if it was a big G that screamed gucci heh cause that's tacky..)
Both of my coats are boss hugo boss. One is a charcoal wool 3/4 overcoat and the other is an insulated navy blue nylon number which has a really sharp silhouette (just a regular coat that falls to the waist and looks better unzipped than zipped).
------------------
Anyway that's me from head to toe. If some stuff is repeated it's cause i pasted most of the post after I had already started with my reply. Oh and in terms of colors I wear a lot of shades of blue and grey, navy and black. In the warmer months, in addition to the blues, I've got all shades from beige/cream to olive (well not really olive but i suck at describing colors)
edit:just looked at post. grammar is really really bad heh. sry i was just kinda listing stuff and not paying much attention to it.