AMBER:
Hi! Sorry this note is random, but I totally met you while you were in Chicago… I had no IDEA your website was Painfully Hip. I’d like for you to know that I enjoy it very much – I think it’s AWESOME.

I need hipness help. I’m a teacher… Do you have any fashion pointers for a young lady who doesn’t want to look school-marmy? My school gets anal about our dress code and sometimes I feel at a loss when I even shop for school…I feel boring.

I need visual help when it comes to making an outfit. I used to be way better at it when I was younger, but lately my fashion needs to fit the activity and I usually am found in a tank top with cardigan and some sort of jean riding my bike. OH, and I love my BlackSpot sneakers.

Teacher dress code = not interesting:).
Jeans on Friday only.
Button up shirts during week preferred. Or some sort of collar. Slacks or (gulp…) KHACKIS Mon-Thursday.
Open-toe shoes are ok, but most people go closed toe. I wear a lot of ballet flats, but hate the button shirt thing. I get away with wearing lots of fluffy Anthropologie tops, but I’m starting to feel like a yuppie clone. It makes me feel gross.

When I first started at the school, I had a lot of old lady teachers gossiping about my “wild style” – and that was the Friday I wore a nice hoodie and purple sneakers. HEY! It was casual day! SO- I am always trying to meld acceptable with personality.

I also got a bad haircut, so I struggle with hairstyles. My hair is too short for my face and way layered…lots of bobby-pins.

SO. That being said – what do you suggest for a lady of 5’2″ with an interesting haircut who loves pants and hates school dress code?

Show how a teacher with a boring dress code can still look cool – That’s my hip website request!

On another note, it was very nice to meet you, your sister, and [her] husband while you were in our lovely Chicago. Your website is in my toolbar and I check it every day. I love it! Keep up the great work.

Yours,
Stacy McKinley

Wow Stacey, what a conundrum! I’m really glad I don’t have to pander to a dress code! I’d probably lose my mind, or at least everyone would think I had, once the repression reared its ugly head on evenings and weekends, when you’d be likely to catch me riding my bike in a maxi dress or donning high heels whilst dying my roots.

Anywho. I do work well given boundaries, so I’ll do my best to come up with a few ideas. Here some experiments in scholarly apparel courtesy of Polyvore (please note, I’m not paying attention to prices on these given pieces as they are fairly easy to thrift/find in sales in most cases, but don’t forget the painfullyhip discount code at lulu*s and modcloth!).

Try playing with menswear.
Equal fashion opportunities for all! Wear your “fluffy Anthropologie tops” and girly hair things with “manly” accessories like a pair of suspenders or a fitted vest. It may give you that touch of whimsical authority that you’ve been missing. Instead of blah khakis, try some pinstriped trousers with a floral top and feminine knit vest. Or a pair of wingtips with some skinny tweed trousers (alter something from a thrift store) and a ruffled top.

Be practically feminine.
Its obvious that a day of chasing a legion of cowlicked young’uns with no sense of self-preservation does not lend itself to wearing things like platforms and pencil skirts, so look for femininity in a more practical form. Gauchos and capris can now be worn to places other than PTA meetings. They have a lovely vintage 70′s sorta feel to them. Hair scarves are your best friends whilst sporting your “interesting” haircut and boat shoes walk the line between femme flats and comfy sneakers.

Go crazy with accessories.
Try some colorful/slightly mismatched accessories to cure your case of the blahs.

Shun the smirks.
The fact that the other teachers are labeling you the “wild child” just for wearing a bit of color should tell you a little about who you’re dealing with. Therefore? Wear that label with pride and soak up the stares like a tall blonde in Shanghai! You should feel lucky you can stand out from the crowd so easily, it takes a lot more for me to get noticed with the circle of friends I run with! Plus think how subversive you’ll feel when you “beat” that anal system by conforming to it, but with wild abandon.

Got a question? Ask Painfully Hip!

More hipness conundrums solved here!

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