Do you have an over-flowing closet, but nothing to wear? End up wearing the same boring things over and over? Or maybe you get really confused and have no focus when you go shopping. Think you know what you like, but fear you can’t pull it off? Well then sweetie, you need to keep reading…
1. Figure out what you love.
Take out the top pieces in your closet that you love, not neccessarily things that you wear all the time. I’m talking about your most special, going-out pieces. Like the overtly impractical cocktail dress that you spent too much on because you had to have it. The over-sized peacock pendant that you shouldn’t wear dancing cause it hits you in the face when you pogo, but sometimes you can’t resist anyway. Your favorite uncomfortable shoes, your grandma’s silk Pucci scarf from the 60s and that hat you sometimes wear even on good hair days. Whatever it is, if your heart goes pitter-pat when you put it on, pull it out. But be selective and forget about trends. Try to lean more toward things you’ve had and loved for a while, not just your newest and trendiest acquisitions.

2. Take a look at your favorite go-to staple pieces.
Pull out your perfectly worn out indigo skinnies. Your Audrey-est little black dress. Your comfy leather shoes, slouchy grey cardigan, colorful vintage sneakers, well-tailored black jacket and very versatile pair of flats. Choose the things you wear the most, while thinking mostly of their aesthetic value; how good you think they look on you, not how comfortable they are. You’re trying to figure out your personal style, not what to wear whilst hungover on your couch watching the 3rd season of Arrested Development.
3. Assess your tendencies.
Ponder your choices and think of a few words that describe your aesthetic. According to my picks, I tend to gravitate more toward 60′s styling and feminine details combined with edgier, more casual pieces. Next time you go shopping, think about these 20 pieces and try to choose things that enhance them and round out a strong aesthetic. But don’t be too strict for too long. Always allow room for your style to evolve. Choose your trends carefully and don’t let them rule your style.
4. Confidence, confidence, confidence…
Do you really want to live the rest of your life worrying about what people think? Those rare pieces that give you more confidence are few and far between. I hate it when people say, “I’d love to wear that, but I’d never be able to pull it off.” Pshaw, my friends, pshaw. With the right amount of confidence, you could pull off zebra-striped overalls, even if you’re not M.I.A. Once you’ve figured out what you truly love, the only thing left to do is rock it! When in doubt (god forbid) sneer, strut or just grin and no one will ever doubt your rockin style choices ever again. And who gives a poop if they do, they call it personal style for a reason.
In conclusion, I think we could all make a new year’s resolution to be more like wee Stella here:
We’re going to be deep in the redwoods for the remainder of this amazing year, but we’ll be back with a whole new layout with translation capabilities for all my international readers (Singapore, reprezent!) Thanks so much to you all for this amazing year (although Painfully Hip is only 9 months old!), I couldn’t be happier doing what I do and getting all your awesome feedback. I’ve virtually met so many amazing bloggers and readers and shop owners over the months and I just want to thank you all again for visiting me every day.




















Nice post! I love your tips. Happy new year, ladies! xx
Thanks for the great posts this year, look forward to 2008! I totally agree about people saying “I can’t pull it off”. Why not? I feel like I can wear anything I want!
excellent post!
Great great post! Love it!
Happy new year and see you soon!
excellent tips. i especially love the bit about our favorite uncomfortable shoes.
Smashing advice for the new year, especially that last, confidence! Hope you’re having a rockin’ New Year, girls! See you in ’08!
Stella is fab! Supermodels will have nothing on that little girl when she grows up…and great tips!
Knowing what’s in your closet is half the battle. Thanks for the inspiration! Happy (painfully hip) New Year!
Love all those pieces after #1. Closet envy here I come.
Will use this advice when I go through my closet this week. Thanks.
Have a wonderful new year and I’m looking forward to future posts!
Excellent advice, I’ll check back next time I have a wardrobe crisis, probably tomorrow! Thanks and happy new year!
great advice but don’t forget to add getting
things discounted
closetlies.blogspot.com
i ship everywhere;)
shop marc jacobs, cheap monday,ksubi, james perse and more
That wee girl has great poses!!!
thanks for the tips! love your blog (this is my first visit). and stella is quite possibly the cutest little thing i’ve ever seen!!
So well put, excellent post! Thanks!
i’ve been browsing fashion blogs for a while now, but this is the first time i’ve ever felt compelled to reply to a post! well-done, you! i think your advice is the best thing i’ve heard in a while, and i’m off to my closet to do just what you suggested
[...] of my new years resolutions is to take my own advice to re-assess and maximize my wardrobe and perhaps finally start my own style journal (thanks, [...]
fantastic post :]
[...] This blog has changed my life in a multitude of ways. My personal style has evolved faster than the Silicon Valley gene-pool. It has also literally helped me become self-sufficient and that has boosted my long-waning confidence. I owe it to my readers to practice what I preach. [...]