This Week I Love …

handbags_with text

… my lovely handbags.

I’ve gotten several requests that relate to how I pick my bags – both for purchase and for daily wear – so I thought I’d tackle both at once today. I spent most of my life as a single bag-carrier, focusing my collector’s eye on shoes and feeling no desire to expand my collection beyond a single oversized black leather hobo. But a stylish friend mentioned that bags afford you the opportunity to incorporate another color into your palette, or introduce a new pattern or texture, or even change the overall feel of your look. That message seeped in over the years and my interest in having multiple bags to choose from was piqued. Bags are accessories, and they really do contribute to your ensembles. I think I overlooked them for years because I felt like I spent so little time actually carrying my bags. I’d carry them from car to work, stash in a drawer, and not use them again until it was time to go home. Never mind that I schlepped them around all weekend and anytime I went out after work … it just didn’t seem important.

But now it does. Since I’m far more likely to be running to five different meetings or errands in a single day, I spend more time carrying my bags. And since I’m an admitted color fiend, I’ve had a whale of a time tracking down bags in various shades so that I can add more dimensions to my outfits.

So there’s your background. Now let’s dig into the questions of choice.

How do I choose which bags to purchase?

I really have two main criteria:

  1. Is it big enough?
  2. Is it a color I love?

For ages I had strict rules about which styles would work, most of which had to do with how the bag could be carried. I wanted a strap that was long enough to go over my shoulder when I had my winter coat on, and short enough that I could carry the bag in hand, arm extended, without it scraping the ground. I still try to stick to that short list, but have found that I really only need to wear my bags on my shoulder when I’m walking for long distances. So I’ve relaxed the rules a bit and have a couple of bags that can be carried in-hand only.

In terms of color, well friends, I’m just a sucker for color. And if I see a bag I love and the price is right and it’s in a shade that I don’t already own, I typically save up as quickly as I can and nab it. I love being able to choose from magenta, teal, and navy in addition to black and brown. I’ve got a polka dot satchel and a leopard-print bag, too, but most prints don’t appeal. I prefer solid colors that complement the colors in my wardrobe.

Brands vary widely. I’ve thrifted handbags, bought from mid-market stores like Banana Republic, and eBayed a TON of fancy-pants brands like Marc by Marc Jacobs and Rebecca Minkoff. (Tips for how to shop on eBay here. Also see this comment for eBaying tips.) I have one straw bag that I adore (thrifted!) and the rest are leather. If I’m looking at a bag online, I always check measurements as I prefer my bags roomy. Depth is the real killer, and anything less than 4″ is likely to be cramped. Other measurements are anywhere from 9″ to 14″ depending on design.

How do I choose which bags to carry?

I have a couple of smallish bags, but the vast majority could hold a watermelon, a puppy, and a set of encyclopedias. Size is seldom an issue anyway because the same items go into each bag: Wallet, checkbook, makeup bag, sunglasses case, keys, phone, business card case. (I generally stash gum and tissues in as many bags as possible, as I’m eternally in search of one or the other!) So I select my bags to either match or complement my outfit. The old question of match vs. go.


Although neither outfit includes actual polka dots, both have loads of black so this bag matches.


Neither of these outfits has any teal, but both have lots of blues and/or purples which complement the teal, so this bag “goes.”


I will also use bags as an excuse to add an additional color on occasion. My bright red MAB Mini is the most likely pop-of-color candidate.

But honestly, much of it comes down to my mood and the mood of the outfit. Structured, ladylike clothes get top-handle briefcase-like bags. Slouchy sweaters and big boots get soft hobos. I am lucky to have so many fun bags to choose from and rarely find that I don’t have a bag that works with whatever I’m wearing. Or pretty darned close.

Related posts:

Are you a lover of bags? How do you pick which ones to buy? (Even if you only buy one and use it until it falls to pieces!) If you have multiple bags, how do you select one for the day?

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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26 Responses to “This Week I Love …”

  1. Olivia

    I adore bags, but I can’t picture getting to a place where I change them daily. Instead I change them about once a month. I have been carrying large bags for a few years because I have small children and I make them work as a diaper bag, and I am really looking forward to moving back to medium sized purses in the future.

    As for purchasing bags, I am trying to buy better quality so l look on eBay. But I don’t know many designer names, which ones are quality, or what a good price would be. How do I know what to look for?

    • Sally

      Oh, Olivia, it is really tough to give eBaying advice, especially when it comes to bags. They are among the most frequently knocked off and counterfeited, unfortunately. But here are a few tips:

      – I wouldn’t presume to list designers for you, but you could start by cruising through Pinterest or some of your favorite style blogs to see which styles and brands you like.
      – When looking on eBay for those bags, make sure that the vendor has a 100% or darned close rating and more than a handful of sales.
      – Make sure the listing includes the phrase “guaranteed authentic” or similar terminology.
      – If you’re in doubt, you can ask the vendor to post photos of the dust bag, branded tags inside the handbag itself, or purchase tags showing the brand name and original price. Many do this without being asked and it helps verify authenticity.
      – Check return policies. Larger vendors on eBay often offer returns, which is a sign that they’re legit. But when I sell I don’t offer returns, and my stuff is all authentic, too, so this isn’t a make-or-break.
      – “Good price” is relative, but if you search for a bag style you’ll probably see multiple bags in that style and can compare prices. Older or more heavily used bags will be cheaper. I’ve paid as little as $99 for a $395 Foley + Corinna Mid-City Tote in perfect condition, but it varies a ton.
      – Use PayPal to pay. It will be a pain in the ass, but if you end up buying something that is “guaranteed authentic” and turns out to be fake, PayPal will likely side with you and refund your money.

      If you’re interested in just investigating handbag brands, hit a department store and handle a few that appeal to you. You’ll get a feel for which styles and designers excite you, and then can stalk them on eBay.

      Hope that helps!

      • Olivia

        That is helpful! I’ve been using your bags to learn of brands and search for them. 🙂

      • Ruth

        The first thing I ever bought on ebay (ok the only thing) was a shopping basket. I had had a great big straw basket that I used for my weekly grocery shopping but eventually the amount I carried in it took its toll, and the handles disintegrated. The place I had bought it from no longer existed so I tried the internet.
        Well, first of all, every site has a ‘shopping basket’ for putting your goods in so the search was near impossible. But eventually I found one on ebay. It was a straw basket with handles, just the thing I wanted. When it arrived it looked exactly as the photo BUT the photo had no dimensions. This basket I was going to use for my weekly shop was about 4 inches across, ideal for a little girl who wanted her dolly to go shopping. Luckily it was very cheap, so I just laughed. And then a friend came to dinner and saw it on the coffee table and admired it, so I gave it to her.
        Caveat emptor!

  2. Tragic Sandwich

    My absolute favorites are from Siren Handbags. They’re pricey, but beautiful–and there’s nothing like them out there. (I’ve been fortunate enough to get several as gifts or at discounted prices, because I know the designer.)

  3. Msboosh

    Wonderfully helpful post! Could you describe the bags shown above? Knowning the brands/styles of these particular bags would be a big help, Thanks!

  4. Andrea

    I love the look of the statement bags, and still sometimes wish I could work them into my life, but I have overall come to recognize that I just cannot justify their size (or price, usually). I am a small-handbag kinda gal. But I made a point this year of upgrading to and incorporating some lovely little cross-body bags and clutches that are super versatile and really give my outfits some finish.

  5. Amy

    As a city dweller, bags I can wear crossbody suit me best. I feel more secure on public transportation and when walking, plus hands free! I also prefer a larger bag. However this style and size can be limiting. Maybe I will submit an insomniac pick for help! 🙂

  6. Anonymous

    When you feature a cross-body style bag, or a shoulder bag, I would like to see you actually wear the bag, not carry it in your hand. If handbags are meant to complement one’s outfit, then it helps to see the bag as PART of the outfit, especially if it’s meant to be worn cross-body, for example. It would help to see how the proportion of “worn” bags work with various outfits, a well as how the color of the bag complements what it’s being worn against. Carrying a cross-body bag with the straps hanging, at arm’s length from an outfit, is sort of like holding a pair of shoes up to an outfit rather than just wearing them.

    • A.B.

      How the bag is “meant to be worn” isn’t necessarily the same as how the person wearing the bag wants to wear it. In the six photos above I see exactly how it works with the outfit.

  7. Pearl

    I do prefer small bags but I can never fit all the things I want in them. I always have a dilemma on what to leave behind. Yes, a big bag would solve this (what a crisis!) but I just can’t wear one.

  8. ChiLibrarian

    I have a several handbags, but I find that whenever I change them, I end up leaving something in my old bag that I want in the new one. What do you do? Buy multiples of things like lip balm so each bag is “equipped” and you just need to switch in your wallet and phone? Do you move everything from one bag to another? I know some people keep lots of things in little zippered bags and pouches, but I tend to not like to deal with opening the bag, then opening a zippered compartment, then opening a zippered bag to retrieve something. I guess this is why I tend to not change my bags very much, although I have quite a few.

    • Olivia

      You might search etsy for handbag organizers. Many sit up in the bag with slip pockets big enough for the small items and then you only have to move the organizer and your wallet. I use one and then I don’t use the bags pockets at all.

  9. Eboni Ifé

    Oh man, Sally. I love that red bag so much!

    Lately, I’ve been carrying my little black crossbody bag everywhere. I find that it goes with everything, and it’s hands free.

  10. BamaCarol

    I trolled ebay last night and treated myself to a couple of new bags! They were not cheap but I was looking for a classic design in a color that I’ll use forever (oxblood for one and cobolt blue for the other). Seeing the way you style your bags has given me lots of great ideas and more confidence to be able to pull it off. I grew up hearing that the shoes and bag had to match but am so glad that idea is long gone. If the bag is a color that I’m not sure I’ll wear often or for many years (radiant orchid anyone?) then I won’t pay much for the bag – I’ll want to see how often it works its way into my wardrobe before investing. And I have gotten my mom to move away from the matchy-matchy shoe/bag idea as well and she is rocking some beautiful colored bags these days!

  11. Ness

    For work, I splurged a bit on an ONA camera bag. As an editor, I often carry around my DSLR and either my iPad or my work laptop, so it’s nice to have something that can hold all of that—plus lipstick, notepads, pens and other miscellaneous stuff—safely. For personal use, I have multiple handbags that I love to switch out in various colours and sizes. Some are leather, some waxed canvas, some a leather-like material but I love using them for a pop of colour.

  12. Kat

    Different bag for every outfit? Yeah, no, totally beyond my capabilities!!!!
    It doesn’t help that I really don’t like the look of most handbags. They nearly always seem over-designed and strange, to me.

  13. Anamarie

    I own a lot of bags, but I have been on the hunt for years for a roomy tote I could use every day. I finally got a super-luxury one for my birthday, and it has been my daily bag for the last month+. I think about my other bags, but am not missing them much. I keep thinking, “cost per use!” and that definitely helps deal with the expense. I also love that bag, and it’s beautiful. That gives me a lot of pleasure.

    I definitely choose bags based on size and how I intend to carry it. I am literally a hand bag woman. I don’t care if the handles can go over my shoulder. The closures have to be smooth and strong (no weak magnets!). I carry a LOT of stuff every day. Most of the items in my bag are enclosed in smaller bags, so if I have to change bags, I just transfer the smaller bags to the new larger bag.

    Even though I have a lot of handbags, I do not own ONE plain black bag!!

  14. Patricia

    These are GORGEOUS! I’m a color-lover like you, but I’m also pretty staunchly a one-bag person… so, my one bag is bright yellow and the haters can deal. (I get recognized for it around town, which I don’t mind one bit!)

  15. Cynthia Peterson

    This is such a great post, Sally! I too love handbags, and have a variety of colors. Since I retired from teaching I have downsized, and find that I use mostly cross-body bags now. I only purchase genuine leather, as I find they just feel and look better. I love Fossil as they are well made and come in gorgeous colors. Danier has some lovely bags too, and they have frequent sales. I have also been able to luck out at thrift stores. My best thrift store deal has to be a Cole Haan Villager black satchel that I don’t think had ever been used (woot!).

  16. Susan

    I have a wardrobe of handbags. For several years, satchels were my preferred style and I have them in black, deep purple, deep green (with rose gold zipper, very pretty), and pewter. This year I have focused more on clutches and I love them. I have black, pewter, red, leopard, navy, white, and tan. I have two smaller shoulder/cross body bags- black calf hair and burgundy. Then there are totes/hobos in yellow, black and red. Finally, I have 5-6 evening bags.

    I used to like having a lot of pockets in my bags but that makes changing more complicated. I now only use a pocket for my phone. I have a smallish wallet, make up bag, folding brush, pen, readers and keys. So changing my bag takes less than a minute and I can select just the right bag for that day’s outfit. Works for me!

  17. shebolt

    Just a question for you, Sally: Do you plan out your handbag wardrobe or do you shop on more impulse (as long as the bag meets your criteria)?

    Thinking over my own bag collection made me realize I never really planned most of it. I think “I need a clutch for the party next week” and go out and buy a clutch that works with my planned outfit. If I happen to be able to use that clutch again, lucky me! I think “I would like a medium-size crossbody bag” then go and buy one. But, inevitably, the bag I chose doesn’t work with every outfit so I buy another crossbody bag and next thing I know, I have 4. Almost always, the first one I purchased ends up being my least favorite of the bunch and never gets used.

    The only bags I’ve truly planned (by color, size, and other features) are the bags I use to commute to work.

    So I was wondering if you say to yourself “my wardrobe is missing a teal bag” and then you go out and buy a teal bag, or if you just happen to see the teal bag for sale and think “yes, I can really use that!”

    • Sally

      And a good one, shebolt! It’s a mix of both. The planned ones tend to go more like this: I encounter six outfits that prompt me to think, “I wish I had a magenta bag because it would be the perfect complement here.” And then I spend ages scouring eBay for the perfect magenta bag. Plenty of unplanned ones, too, and those usually happen when I’m shopping for someone else – a sale picks post or an online style consult client – and happen across a bag in a color I don’t already own and begin scheming.

  18. marsha calhoun

    The only thing I care about in a bag is whether or not it leaves my hands free, so a cross-over is the only option (except on the once-every-10-year occasion of a formal dress). And the idea of switching contents from bag to bag every day, even if it only takes a minutes, wears me out just thinking about it! Also, I see a danger of inadvertently using a bag to tie together an otherwise less harmonious outfit, which would mean that during the ninety percent of the day that you are not carrying the bag, you don’t get the benefit of its stylistic punctuation (much like a hat that complements the outfit so well that you are reluctant to take it off, even indoors). But bags themselves can be intrinsically beautiful, and I must say that those in your photos are attractive – if I weren’t so lazy, perhaps I’d be tempted to buy a few more.