Reader Request: Handbag Basics


Melinda dropped this question into the suggestion box:

I’d be interested in a post on purses and bags. I always feel ridiculous carrying any kind of purse. If it’s big, I imagine myself as a 4 year old girl playing dress up. If it’s small, it just seems too twee and fiddly. I admire women who can carry contrasting colored or interestingly structured bags as if they are natural parts of their wardrobe (instead of, oh-god-I-need-somewhere-to-stick-my-wallet-and-phone). So I’d like to see sort of a “Getting Started for the Bag Wary” post.

I am simultaneously excited to tackle this request, and extremely daunted. I am still fairly new to a multi-handbag lifestyle and all things bag still thrill me, so I’d love to share my tips. But even with my thoughts here and yours in the comments, I’m not sure we can cajole Melinda into overcoming her bag reluctance. Well, let’s try and see how we do.

What do you need to carry with you?

Most of us take things with us when we leave the house, and many of us take more than can fit into our pockets. So if you’re curious about adding a bag or two to your life, the first thing you need to consider is the specific things that you need to cart around. How big and heavy are they? Are any of them awkwardly shaped? (For instance, do you carry a tablet with you? Is your wallet the size and shape of a brick? Do you need to keep a pair of flats on you at all times?) If you are curious about the multi-bag route, can you compartmentalize your stuff so it can be switched easily and quickly between bags?

Your stuff will help you determine how big your bag needs to be, how durable its material needs to be, and which shapes just won’t work.

What do you want your bag to do?

Carry your stuff, I know. But secondary bag considerations may include: Look corporate and professional, work with your winter coat, enhance your outfits, go with everything you own, express your creativity. This bag is going to travel with you wherever you go. What is its visual job? What elements of your body or style does it need to work harmoniously with?

What are your comfort priorities?

Since this bag is going to travel with you wherever you go, it would be great if carrying it didn’t irritate the hell out of you. Do you need to have both hands free? Shoulder bags only for you. Back or neck pain? A lightweight crossbody or stylish backpack, perhaps. Can’t stand fighting with your parka and purse strap? Try a hand-held design. If you’re not currently a handbag person, think about other bag styles you’ve tried – messenger bags, school knapsacks, briefcases. Which of these felt natural and comfortable?

I’ll use myself as an example: I can do a handheld bag, but am much happier if it also has a shoulder strap in case I unexpectedly need my hands free. I generally prefer a bag that has a wide strap so it doesn’t cut into my shoulder, and ideally it would be long enough to sling over my shoulder but short enough that I can carry it in-hand without dragging it on the ground. I have one rectangular bag (this style), the rest are flat. I don’t care if bucket bags are all the rage, if a bag bonks against my side like a tetherball I see red. I need my bag to hug my side.

Which bag styles appeal to you?

Hobos, satchels, totes, crossbodies … got a favorite design? Try not to think about this until you’ve considered your stuff-hauling and comfort priorities. You may love the look of a frame bag, but if you can’t wedge your stuff into it and need a shoulder-slung style, you’ll have to love it from afar.

And then? There’s gonna be some trial and error. If you haven’t habitually carried a handbag in the past, it will take some time to get used to it. And once you’ve gotten used to it, you’ll probably discover a few things about your bag that drive you bananas. You need to know your use patterns before you can really hone in on the perfect bag. (Having to deal with top zippers is my pet peeve. Trying to unzip a bag to reach a ringing phone while simultaneously balancing the bag makes for an odd little jerky dance. For me, anyway.)

So what should Melinda do? I’d highly recommend either borrowing a few bags from a bag-loving family member or friend, or thrifting a couple of promising shapes and sizes. Explore a handful of styles, and try to carry each for a couple of days before passing judgment. Before you can start making your bag an element of your outfit, you need to find out which style suits your needs and get used to carrying it. And honestly, people who incorporate bags as outfit elements generally LOVE handbags. That route is not for everyone. There’s nothing wrong with having one versatile purse for 99% of your life and a sparkly clutch for the other 1%. (Clutches can be thrifted!)

Hopefully that was helpful, but I’d love your input, too. Do you remember how you became accustomed to carrying a handbag, and which styles you tried before you found your ideal? Or are you just now trying to figure all of this out and have other tips to share?

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Originally posted 2015-02-12 06:50:56.

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13 Responses to “Reader Request: Handbag Basics”

  1. Ruth Slavid

    I’m so glad that you have shown a red handbag, because one of my rules is ‘a red bag goes with everything’. You should also think about security – it isn’t good to have your wallet in a backpack on public transport – and accessibility ie can you get to those vital things really fast.

  2. Monica H

    I am also a relative newbie to styling handbags. Sally made several excellent suggestions, and her compartmentalization tips are pure genius. But I will add one more thing that really helped me – when you are considering buying a new handbag, try it on with an appropriate outfit and see how it looks in the mirror. Perhaps this advice is glaringly obvious to some, but it had never occurred to me. Bags which seem similar on the shelf felt or looked different when I “wore” them. Bags of different shapes and sizes seemed more or less flattering, and more or less annoying.

    Also, when all of this seems overwhelming, just buy the bag that makes you smile. 🙂

  3. Rebekah Jaunty

    I like messenger bags and shoulder bags, but any shoulder bag must have ONE STRAP. Any time I’ve bought a bag with two straps, one strap always falls off my shoulder. Maddening.

    Another thing to consider (after what you need to carry and what feels comfortable) is where the bag hits on your body; a short shoulder bag or clutch tucked under your arm draws attention to your bust, a long shoulder bag or messenger may highlight your hips. What will feel balanced to you? What sounds like fun?

  4. Margot

    For me, compartmentalization is key. I tend to carry a large bag because I’m always schlepping random kid-related stuff, or mail, or snacks, etc. I got a little nylon purse organizer that is a miracle, and I keep my lipsticks in a little zipper bag. I also always have a glasses case. Keeping everything in its own container helps me shift stuff into a different bag really easily. I also need either a shoulder bag or a crossbody because I need my hands free. My pet peeve: bags with flaps over the top. I need a purse that is open on the top so I can easily reach in and grab stuff without futzing with a flap that I have to fold back first.

  5. Sonja

    I could say a loooot about this, as I’m also not too keen on handbags but always schlepp half of my household around with me. Maybe just one point to have in mind when you’re new to this game: Buy a bag that is in synch with your frame. I’m petite with an hourglass figure. I can wear a small crossbody bag or a big one if it is longer vertically than horizontally (I hope that makes sense). If I wear a big crossbody bag or one that is very long (horizontally) it looks strange on me, as it meddles with my figure and makes me look broader. Interestingly enough this is not the case if I wear a handheld big one (in my hand or on my shoulder). Maybe because in that case it sits on places of my body where I’m already broader, so it doesn’t look off.
    Ah, also: Buy a bag that’s lightweight, because you will quickly add weight to it. I always end up buying a black one from Kipling, because they are versatile, super light and last for years.

  6. JB

    I’d like to second the point about security. For me this is primarily an issue when I travel, but it can also be an issue for subway riders, concert goers, and anyone else who might find themselves in a crowd of strangers. Those top zippers and flaps that make it harder for you to get to your stuff? Well, they also make it harder for would-be pickpockets to get to your stuff. It’s a trade-off. Just something else to think about.

  7. Lisa Wong

    I have a core group of about 10-12 bags I love in my closet, but I get lazy about switching them out so I might swap in one, use it for 2 months straight, and swap in another. Lately I’ve been all about my Longchamp tote, which is super light and waterproof but big enough for all my essentials, plus snacks, gym gear, a water bottle, and a portable umbrella. The perfect office-to-workout bag!

    One thing to consider for multi-bag newbies: Get a couple of wallets and makeup pouches (for corralling loose stuff like hair pins, lip balm, etc.) of different styles and sizes so you can switch between different-sized handbags easily. When I switch from my office tote to a smaller crossbody handbag on weekends, I also take out only what I need from my larger wallet (credit/debit cards, transit pass, ID, some cash) and transfer it to a slim cardholder wallet. I’ll also only grab the essentials (lip balm, hand lotion, eye drops) from my larger makeup pouch and slip it into a smaller one.

  8. Shawna McComber

    Great tips, Sally. I think experimenting with thrift shop bags is a good idea to find out what styles and features work best for a person. At this point in my life I know exactly what I want in a bag and do not care at all what is currently in style. I have a few different bags but am not interested in having something different for every outfit. I generally choose bags in neutral colours, lighter ones for summer, I insist on real leather and I want a strap long enough to wear cross body but will sometimes wear it as a shoulder bag. I like the main body of the bag to be relatively soft and flat, as like you I do not want it bumping against me or protruding greatly and your tether ball comparison made me smile. I have a mid-sized basic cross body bag that I use for short outtings and a larger tote that I use if I am out for a whole day and need to carry more. The tole is a bit more awkward to carry around then a cross body is but the straps are long enough to put over my shoulder. I have a few small bags for more formal situations and a satchel in red that I bought as a treat for myself but do not find I use it much. It isn’t well suited to my lifestyle but I do love it and sometimes it works instead of the tote.

  9. Cynthia Peterson

    I love handbags, and have gone through various stages in terms of size. Now that I’m retired I no longer need the larger bags with various compartments to hold lunch, two large sets of keys, files, as well as makeup and other personal items. I first switched to small crossbodies but soon found I couldn’t carry my sunglasses as well as my other necessities. Now I love larger crossbodies or shoulder bags. My must haves: leather, interesting shape, texture, color; exterior pockets for keys and phone, zipper top, handles long enough to fit over the shoulder of my coat. I purchased a handbag organizer and can now switch bags almost instantly.

  10. Erika

    Rummage factor. I need a bag that’s wider than it is high, it’s soooo much easier for me to find things in it. I prefer leather simply because it lasts well and feels lovely. I also want a choice of handles – both hand and strap. Enough small pockets to manage keys in one, lip balm in another, hand cream in a third and phone in the fourth. Bonus points if there’s somewhere to tether my sunglasses case rather than having to scrabble about for it in the bottom of the bag.

    Try stuffing all your goods into a bag before buying it (not possible when you’re ebaying) or figure out the minimum dimensions you need. And a big one that I don’t experience but go all buggle eyed at my friends – slim down your wallet. Seriously, what is with those enormous wallets?

  11. Charlotte Jones

    I m very particular about my bags. The straps need to be a certain length since I’m short, it needs to be a zippered top, and be wide and deep enough to hold my stuff. I used to buy black only in the past, but then I started buying black/brown, red, and metallic. The metallic goes with everything, but the perfect color is hard to find. I just bought a red one yesterday from Boscov’s. Love it!