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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Share Your Thoughts With Us

  • kindled

    I sympathize with the original poster/question ask-er. I buy a lot of fancy leather bags, but I’m actually an ecologist, which means the bags I use are giant canvas totes that can get gross in the lab + waterproof backpacks and slings, that can carry gear out into the field. There is really no place for beautiful and pricey leather bags in my life, but I use them grocery shopping, getting coffee, and other minor tasks that truly do not require a pricey handbag. But what’re you going to do?

    • Mya Wilkes

      I’m with you on this. I carry my bags wherever and whenever I feel like it. I have a colleague at work who teases me (very nicely and playfully) about bringing my nice bags to work. While we work in a corporate environment, she prefers not to bring her designer bags to work but save them for nice outings over the weekend. I always say to her that I want to be able to carry my bags everyday and everywhere and for what they cost, that’s exactly what I will do.

      • Sonia

        I’m with you on this one, Mya, I bring all my nice bags to work when I’m working in the office. But, on those days that I go out in the construction field, I’m carrying either all my stuff in my pockets of my jacket and field vest or I’m wearing a crossbody. I bought my bags to carry and I’ll carry them to the office, the grocery store or the movie theaters. If they seem out of place to others, I don’t care. I bought them, I’ll wear them wherever and whenever I want. Oh, and by the way, I am a woman of a “certain age.” Great article, Amanda, I loved how it brought out a variety of responses and comments.

  • PJGambler

    It can also be relative to with whom you socialize. If you’re with a group who would never think to indulge themselves with a bag costing more than $100, you can feel out of place carrying a recognizable, pricey, designer bag.

    • Winn

      Why would that make you feel out of place? That my bag might cost more than the bags of some of my friends doesn’t make me any different from them- for better or worse.
      If there’s one thing certain reality TV stars have proven, it’s money doesn’t buy taste. Expensive accessories are no guarantee that anyone looks any better than someone with less expensive items.

      • PJGambler

        No argument—it may be obtuse logic or over sensitivity on my part, nevertheless, it’s how I feel. There’s a time & place that’s appropriate to wear my luxury items.

  • FashionableLena

    I like this question as a similar one is posed on TPF. Most of my expensive/designer clothing come from resale/consignment/thrift stores because I am not really a clothes horse. I also realized when I was around 30ish what I like to spend my money on (handbags, sunglasses, jeans), and my closet reflects that. My husband recently told me that I have a lot of black shoes. Since shoes aren’t my thing, I find it easier just to buy black.
    As far as social circles go, I’m always the one with the pricey handbag. They don’t get it, but I don’t get spending hundreds of dollars on shoes. To each his own. Wear what you like. When you look good, you feel good.

    • anon

      Ditto! For me, personally, it can also go as “when you feel good, you look good”. When you’re confident in your choices, it shows.

    • Sonia

      Ditto for me too. A great handbag makes or breaks a LBD or even a silk blouse and jeans. As my dad used to say, “When you look good, you feel good. And, when you feel good, you do good things.” I feel confident enough to conquer all when my outfit looks and feels put together.

  • B

    Love this! We as women are often way to hard on ourselves and I love this mental reality check. Great job!

  • AV

    “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.” — Aaaaamen, to that sister. It’s nice to have nice things, but that’s all they are….THINGS. Material possessions do not define you or control you. If you have a fancy bag and don’t want to dress similarly to run errands with said bag? Rock that juxtaposition. You earned it so who cares what anyone else thinks? Find what you love and let it kill you!

    • Deborah

      . . . and I believe that when you’re carrying a fantastic bag it elevates everything else!

      • my thought

        But sometimes, it doesn’t. You don’t have to be dressed expensively, head to toe, but you do need to think through your whole look – does it project the image you’re trying to achieve with the bag, or does it look incongruous. Adding a nice bag doesn’t always ‘cover over’ everything else – you need to look at the whole picture.

      • Deborah

        I do respectively disagree. My bag can make even a run-around outfit like jeans and simple white T look fantastic. Although I do agree that even that outfit would have been thought out.

  • HfromT

    Amanda, first of all, I love the way you write. There is so much about this post that I find very comforting (I think that’s because I can hear myself giving similar advice to my daughters!). It has taken me a very long time to become completely confident in my choices, and I can now honestly say that I dress for myself, and buy gorgeous accessories that make me happy, regardless of the fact that I wear cashmere sweaters and jeans 80% of the time. Great post, and I love this new pb feature!

    • Thank you so much! This question really hit home with me, and I’m glad the asker sent it in.

      • shueaddict

        the asker hit the spot!

  • C

    Amanda- this was lovely! I’m looking forward to more Ask Purseblog posts!

    • Thank you! We’re looking forward to writing more.

  • Pam

    I, too, am of a “certain age” and I find that a certain amount of freedom comes with age. Thirty years ago I wouldn’t wear jeans with a fur jacket. Now, I wear what I want & carry whatever handbag I like. At this point, I try to please ME, & do what makes ME happy.

  • Cara M

    Love the new advice column! I actually love the fact that my bag might kick my outfit up a notch. I like being out to walk out the door in jeans and tshirt knowing that my bag and shoes are doing all the talking. :-)

    • Glad you enjoyed it! We’re going to try to do one per week.

  • KG

    I trot out my handbags where ever I go: work, grocery shopping, dinners, etc. I sometimes look like I just rolled out of bed. I DON’T CARE. I love my bags and for the money I spend on them, I certainly will get good use out of them.

    • Winn

      Agree. The fact that I have nice bags doesn’t mean I’m not allowed to leave the house in yoga pants and a pony tail to run to Target.

  • seres

    Loved reading this. Beautifully considered, measured and kind.

    • Thank you so much for such a kind compliment.

  • kemilia

    I have some very nice bags (and I am most definitely of a certain age), but none of the logo kind, so really no one knows that they are anything special, except me. I am not a fancy dresser at all–jeans, sweaters, clogs, sandals, whatever works and is comfortable, but I love my bags (mostly Bals and BV) and really, the only time anyone recognizes them for what they are is when I am in NM or Nordstrom or LV.
    A nice handbag just makes me happy–and my friends would die if they knew what they cost (while I’m wearing a baggy sweatshirt and flip flops).

  • This is so lovely! Sometimes I get sucked into the crap attendant to the world of luxury goods, but posts like this make me remember what it is really all about. Thanks Amanda.

  • VividTexas

    Loved the column…and looking forward to reading more! I’m 55…not sure if that’s “a certain age” or not, but I wear what I want when I want. As another commented, I love that my shoes and bags kind of “elevate” my uniform of jeans, t-shirts and cashmere cardigans. Life is too short… what makes you happy, forget the “noise” in your head…most of my friends have no idea what I paid for my bags; good thing I bought the bags for me and not to impress “them” :)

  • klynneann

    Everyone’s got their thing. Some people spend money on shoes, some people take extravagant vacations, a friend of mine has a horse – I like handbags! Don’t save your bags for “special occasions” – every day is a special occasion because you never know when it will be your last. Use them and enjoy them!

  • Sandy

    I have never understood this…but so many write about similar problems. First of all, why spend money on inferior handbags just so you can carry them to work or when you are not dressed to the nines! That expensive bag is just as pretty with my workout clothing. Wear them wherever and whenever …all the time. Never, never let anyone make you feel less than wonderful…hold your head high…unless you are looking down to admire your fabulous bag LOL!!!

  • Jeannie Shmina Greenwald

    Great essay! Spot on.

  • Purseloco

    I guess I am “a certain age” because comfort is starting to be my priority over whether I look a certain way, now when picking a bag, the question is can I carry this bag all day or will my shoulder or arms be hurting at the end of the day. Fancy or whether I am good enough doesn’t play in it anymore, now it is, will I have to take some ibuprofen.

  • adguru

    Well, ladies, I’m definitely of a certain age (64) and semi-retired/freelance from home so I have no need to dress up 90% of the time and am usually in jeans. That said, a nice (ok, Chanel, if I’m honest) bag simply makes me happy. It is always “fancier” than what other women in our circle are wearing but I don’t let it make me uncomfortable. Instead, I enjoy the look, the quality of the lambskin, and the luxury of something that makes my ordinary day feel a little more special. It’s like having nice sheets, a wonderful-smelling shampoo, or anything else that gives you pleasure. So my advice is to enjoy your bags, and if you want to upgrade your look a little bit, add good jewelry or a scarf to your casual outfit, give anything you don’t feel great in to charity or sell it online, don’t save the good china for company, and celebrate the glories of being you!

  • Mydogsmooch

    This post makes me chuckle. As i read this, I have just returned from a session with my physical therapist. The conversation was that having spilled coffee on his originally shirt, he was nervous that his “affluent” clients would notice that his polo shirt was from Target. I was fascinated by this, and said that i didn’t notice android don’t care. He said, of course not, you are not like “them”, you are not affluent. Curious, as I am wearing $1500 Chanel shearling boots, and carrying a $4000 Chanel bag, and $2000 Chanel woc. I should mention that I was also wearing Fila baggy sweats, a $4 old navy tank, and a $10 long sleeve polo shirt. perception is everything :-)

  • Gia

    Women are always worried about others think. F that.
    If u buy a beautiful bag to put on a shelf, or wear it, just enjoy it. Nobody has to tell you to wear or not, feel guilty or not. When I am 80, if I get to 80, will I give a s**t what anyone thinks? No. Nor should you now. Live and know the choices you make are for you and not to please someone else…a stranger even.
    Sometime I just love to look at my bags…you know admire, cherish, sounds like love.
    Yes I love my bags.

  • Shabl

    Beautifully written and answered with grace, logic and kindness.

    • Mya Wilkes

      I agree. It was well thought out. Amanda did a great job!

  • Adrianne

    My family always gasps at what I would pay for a handbag. One actually noted I could fly my family to a nice vacation for “that price”! I don’t care! Purses/handbags are my thing. I love them and treat them so! And last I checked my family wasn’t starving nor do they lack for anything! I’m not a shoe girl…although I do appreciate a nice one…I’m a purse girl. And I carry them with my yoga pants and tees!!! Lol!!! Like Amanda said you earned the money to buy that bag, you rock that bag!!!

  • Molly

    Do the clothes fit?? Sometimes that’s all there is to it, you know. I discovered after losing almost 10 kilos, and still wearing my old clothes , that it only takes a super fitting pair of jeans, the right heels and Bingo!! Everything looks perfect. Fit and Heels, that’s really all it took for me