How to look less like a strict teacher / librarian when wearing protective styles?

[Angels+Eyeliner]

I wear milkmaid braids quite a lot. They're easy to do. You can get fun little clips (I have little snowflake clips that I put on the end of my braids, or a big snowflake and cloud for my fringe right now). You could try mixing up your parting a bit, I think buns look less severe with a side parting that pulled back or centre parted. What I like to do when I have plenty of time and want to look more punk than usual is French braid the smaller side of my parting until the nape of my neck and tie that off, do an equivalent braid on the other side (leaving my fringe and part of my hair flopping over it) and then bun all the bits at the back. It adds a bit of interest and isn't at all librarian-ish.

Although, I'm going to be perfectly honest here, you're worried about it because he had a teacher who wore the same hairstyles. That's really his problem, that he associates your hair with her and thinks of strictness, rather than anything wrong with your style. So do what you like, and stop asking him if he likes it.

[Kendrix]

You know, I get the same sorts of comments occasionally. Even my grandma says I dress old. I don't have bangs, but if I want a bun style to look younger, I loosen the whole thing. I have a face frame through so I have shorter bits to pull out.
Buns to the side and low definitely help. Sometimes I also wear milkmaid braids as well and that does liven up a look. And side braids.
For oiling the braid tassel, I HAVE FINE HAIR TOO. I actually stopped using a ponytail holder altogether because of slippage and because I like to make as short as possible braid tassels. I use a 3-4 inch piece of plain waxed dental floss. At the end of my braid, I hold one end of the floss between my teeth, the other end with my hand and my braid tassel with my other hand. Then I TIGHTLY wrap my braid where I want it to end. After a few go-rounds, I tie it off tight, clip the excess bits of floss with a cuticle nipper or tiny scissors and it's done (though mind the little strands that poke/fray from the braid). As long as I get it tight, it stays through me sleeping on it and I have slippery hair. It's my favorite alternative to worrying about elastics and damage.

[Robot Ninja]

Wearing a bun on the crown of your head looks more ballerina than schoolmarm to me, especially on a young person. If you leave your bangs out of your bun, it will automatically make it look less severe. Where I live, a lot of young women are wearing high messy buns with headbands; again, if you leave your bangs out and use the headband as decoration rather than a utility thing it'll look less severe.

[DreamSheep]

I find bangs and side pieces can help add some dimension to the face without the pulled back look. You can also fake bangs from your bun if you don't have any.
Folded plaits, crown braids, milkmaid braids...

That said, you might be able to slowly change his impression of buns. I find most people prefer my hair down, but my bf says he finds my buns elegant and usually appreciates my hairtoys.
Sometimes my ends splay out so I feel from the front my buns look more "punkish" than "strict librarian".
Another option could be to add some temporary colour to your hair? That way your buns and braids could show some colour which would break the "conservative" image.

[missblueeyes]

Thank you for all the input, I really appreciate it! I'm definitely loving the XO-braids and the faux-hawk. I'll definitely experiment with these when I'm working or running errands. Temporary colours are really tempting for me as well but I do think they'd turn out to be more of a permanent thing on my bleached ends so I've stayed away from them for now.
Also, please don't get me wrong, I think neat buns look really great, I just don't see them on me just yet. I'm just looking for some hairstyles to add to my repertoire for when I need to get it out of the way. I usually leave it loose when I'm at home or when I know I can easily detangle it every couple of hours, which is basically anytime I'm not working.

[pearlsandpinups]

I don't know if you've ever checked out her blog, but the Freckled Fox has some wonderful long hairstyle tutorials that don't look librarian-y at all. They're not all protective and she occasionally uses heat tools but there are some great, really pretty ones on there that are very hair friendly!

[Larki]

You could add accent braids to your bun. Like a lace or French braid along the side going back into the bun.

[yogagirl]

Have you seen the high sock bun with the upside down French braid going into it from the bottom? I think it looks frikkin awesome! You might enjoy it with a messy bun on top.

Just google: sock bun zipper

Or see this version with a Dutch braid: http://vimeo.com/53953604

Also, as others have mentioned, I like to make my buns a bit messy and leave my bangs out to soften the look.

[Madora]

How to Pouf your hair in front:

1) Bend at the waist
2) Bring all hair in front of you, like a curtain
3) Detangle all hair carefully
4) Bend head down so it is facing the floor
5) Grasp hair in hand, then divide in 3 parts for braiding.
6) Do not start the braid too close to the scalp! Try to start the braid half an inch or an inch up from scalp. This helps create the "pouf" at the end
7) Braid hair down to ends/secure with hair friendly elastic
Hold braid flat on top of head (a trifle towards the back of the head), coil. Pin with hairpins at the 4 directions.
9) With any luck, you have a braided bun..with a little "pouf" in front!

Inversion braiding:
1) Bring all hair in front, like a curtain/detangle gently with wide tooth comb
2) Head should be down -- steeply
3) Divide hair in 3 sections.
4) Holding the hair straight up in the center of your scalp, start to braid about
two inches ABOVE the scalp (not next to the scalp as in regular braiding). Braid slightly loosely
(either Dutch or English style)
5) Braid down to end/fasten with elastic...or leave loose
(I don't fasten with anything and only braid until I have about 2 inches of tassel left
6) Take the braid. Hold it flat against your head with your hand. Start to form a coil (circle). Use the other hand to pin the bun with crimped hairpins in the 4 directions. Tuck in tassel
7) Bingo: one handy dandy single braided bun!
This method also works for a 2 braid bun and some other buns
Special note: It DOES take a bit of finagaling to get the position of the braid situated on just the right spot on the top of your head. You want to aim for the center of your head or slightly to the rear of center.
ALERT!: By beginning the braid 2 inches (or slightly less) ABOVE your scalp you create a lovely little "pouf" of hair around the forehead (and sides, sometimes), so you don't wind up with the slicked back "otter" look

[lunalocks]

You might want to reconsider using a cool fork or stick to keep your hair up. I have found several bun styles that do NOT look severe/librarian by experimenting. There are cool forks out there. Also try spin pins. Once I passed waist, I gave up elastics and am still growing out their damage. I would love to have my hair down all the time, but can't as the longer it gets, the more it needs protecting.