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Looking young is a blessing and a curse. If you dress your chronological age, you look like you're playing dress-up; if you dress like your apparent peers, you might as well bring your lunch pail! As a result, it's easy for your fashion to funnel into work clothes and all-too-basic basics. My advice: spice up the comfort looks with vintage pieces that, while mature by definition, add one-of-a-kind flare to separate you from the mall crowd. Skip the t's and seek out vintage knits and dresses with beaded details; these pieces will bring charm to looks that feature flats and sophistication to outfits you create when you step up to higher heels. Translated into modern trends, retro style is a great way to forge your own personal look. What's old can be new again; and more importantly, it can be totally you!

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Start small! Don't be so quick to ditch the denim for rejuvenated style. Instead, look for washes and fits that differ from those you wear now. If you usually go for flared cuts, go for straight legs; if your jeans are usually mid-rise, aim for something higher. The trick is to go for the most change without making yourself feel uncomfortable or self-conscious. So not chic! So keep your t's, but skip anything with words or logos. Stick with solids; even a plain white V-neck looks great with chunky necklaces and bangles. For additional, casual chic, you might even consider replacing your traditional diaper bag with a trendy, high gloss tote. As you ease back into heels, don't be ashamed to shop for sturdy mids in bright colors or funky animal prints that will ramp up your style while keeping it playful for your play date!

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Coco is a great choice! She might initially guide you toward more conservative style, but don't forget that she has a sexier side, as well. If you need a clean, classic look with a modern twist, try pairing Coco with a solid button-up and a pencil skirt in a graphic pattern. When you're ready to get a little more daring, some liquid leggings and a sheer-as-you-dare ruffled blouse will make for one hot outfit. Finish either look with a tuxedo jacket and prepare to be complimented!

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Radhika, when it comes to platform pumps (and heels in general), I don't recommend taking a "just go for it" approach! Most likely, those strutting girls only appear comfortable because they are accustomed to their heels; not because the heels are comfy. So rather than attempting to endure an entire evening in pumps and in pain, try spending a little time in the shoes before you actually wear them out and about. Start with something easy, like an hour, and gradually increase the time you spend 'practicing.' By the time your plans come around, you'll be primed and ready to do a little strutting yourself.

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Step out of the college years and into a new decade, Natalie. Start with things that inspire you: favorite colors, films, art or music. Whose style do you admire? Ask yourself what you want your look to say about you? Fashion is no different now than when you played dress-up as a child, so don't take things too seriously and be willing to try things on. You can always take them off! Shoes are a great place to start changing things up. The right shoe can transform many an outfit.