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Last Friday, we asked you to submit your burning questions about handbags, accessories and personal style, and you responded with lots of interesting queries and conundrums. We’ve picked one of our favorites of the bunch to kick off our new advice column, and it hits on a nagging insecurity that a lot of fashion lovers have–what happens when your wardrobe feels a little bit fancier than you are? Check out the question and answer below, and don’t forget to submit your questions to for a chance to be featured.

I am a woman of a certain age (soon to be approaching retirement age) and I have a pretty nice handbag and accessory collection. I almost never discard a good leather handbag because every time I have I’ve regretted it. However, I often don’t feel like I dress well enough to justify my nice handbags and I tend to save them for special occasions. Do you have any advice for an average woman who loves handbags and how to dress accordingly without looking out of place at work and everyday activities?

If working in fashion has taught me anything, it’s that what we’re really doing when we buy clothes and accessories is manipulating perceptions, both others’ and our own. We want to look capable, elegant, successful or special, either to telegraph those traits to others or to reinforce our own self-perceptions. It’s understandable, then, that finding yourself in possession of an accessories wardrobe with which you don’t feel you entirely match creates something of a disconnect.

There are two ways to bridge the gap. First, you can work on shifting your perceptions of your bags and yourself. Second, you can upgrade some little things about your everyday clothing that might make carrying an expensive handbag feel a little bit more appropriate.

Brands spend a lot of time and money ensuring that we perceive their goods (and especially their accessories, which are the financial engine of most fashion companies) as aspirational and luxurious. That marketing works on most people, even those who think that they aren’t affected by it; it usually even works on me and Megs, who should well know better at this point in our fashion careers. A biproduct of that marketing success, though, is the quiet anxiety that can set in when you stand back, look at the things on which you’ve spent your money and feel like you’ve stocked the costume department for a movie based on a slightly better version of your own life.

Although, at 29, I am not yet of a certain age, we all deal with the occasional insecure feeling that we may not be able to pull off something that we’d love to wear, or do, or create. In those situations, the thing that works for me is to remind myself that I am, by the very virtue of owning something, better than it. It is not fancier than me, it is not too good for me and I can do with it whatever I damn well please. I’m the one who got up in the morning, went to work and earned the money that put it in my possession, and with that comes the liberty of choice. It is, after all, just a handbag. My handbag. And if anyone should quarrel with my decisions, then they can put their money where their judgmental mouths are, buy their own bag and wear it differently.

Sometimes you don’t need a different wardrobe. Sometimes you just need a pep talk.

If, on the other hand, you feel like taking your beautiful bag collection as inspiration to refine other parts of your wardrobe that you don’t really love, then there are some simple ways to do that. Get rid of knits that have pilling or anything that’s been through the spin cycle one too many times and has lost some of its original shape. Be brutally honest about what is worn out and what doesn’t make you feel your best and sharpest, and get it out of your life. Replace it with stuff that makes you feel like your best self, whatever that is. Maybe it’s a couple sharply tailored new blazers for work or a some cashmere sweaters that feel like wearing an especially soft cloud–the what doesn’t so much matter in this equation. This is an out-with-the-old-in-with-the-new process that we all know how to undertake, and dispossessing yourself of things you don’t need or want can certainly lighten more than just your literal load.

For most of the women I know, though, this isn’t an issue of what does or does not actually reside in her closet, but rather, of the space she’s given up in her head to all the doubting voices that she’s heard in her life. It’s about time those voices got a hobby and let us live, though, and that means you no longer need to have more regard for your possessions than you have for yourself. You’re just as fancy as you need to be, and you always have been.


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