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Nothing about my upbringing led me to have a knack for these fashion things. I had no glamorous mentor from which to model myself or emulate, no chic relative passing me down heirloom jewelry. My mother’s greatest pleasure was heading to the local nursery to pick out ornamental rocks for the yard. Her accessories were a pair of stiff leather gardening gloves and rubber-armed pruners. Dad collected not cufflinks but .50 cal rifles. Coupled with a uniform-required, private school education, I was left in the dark on what it even meant to dress well. When I did go shopping, my money went to fund strange purchases, like a zebra skirt from Guess or a blue lame top from the mall.

By and large, I am thankful for growing up shielded from the rigorous expectations of fashion. It did, however, put me on the tail-end of the learning curve once I edged my way into adulthood, where my friends often held themselves to standards of the Saint Laurent variety.

It’s been a long journey, but I’ve picked up a few valuable lessons along the way. Though I have never been accustomed to blowing my life savings on clothes, I have learned, however, that there are items worth splurging on that will make all the difference in your wardrobe.

1. Buy a nice wallet. I used a man’s wallet (that I got for free) for quite some time, stuffing it full of cash and receipts until my friend started calling it “The George Costanza Wallet.” A Comme des Garçons will serve you well.

2.  Buy a better boot. A good, expensive leather boot – if well taken care of – will last you a lifetime. Just ask your dad.

3.  Invest in a coat. If you have to save for an entire year just to buy a really beautiful winter coat, I recommend it. After moving to New York, I was shamed out of my puffy coat, and for good reason.

4. Avoid cheap leather. Nothing grinds on my nerves more than a cheap jacket that looks like you’ve skinned an old family room recliner. If you can’t get something buttery and nice, find another fabric or scoop something up secondhand.

5.  Take care of yourself. Your face and body are accessories that you’ll be stuck with for a long, long time. Buy good skin creams. Eat good food. Hit the gym. When you’re 50, you won’t regret those purchases. —Jenny Bahn

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