Ask Belle: The Laptop/Work Bag Conundrum

Mar 5, 2012

I am constantly bombarded with emails, comments and tweets asking me for a stylish laptop bag/briefcase that will hold legal size files and a computer.  I mean, if I had a dollar for every time someone asks me to conjure this magical bag from the ether, I’d be retired to a private island in the Caribbean where the only law would be a mandatory dress code.  Finding such a bag presents numerous challenges, but I’ll just hit the high notes.

First off, any bag that’s going to be large enough to hold a 15″ laptop and 16″ legal files, plus essentials is going to be gigantic.  It’s also going to use a lot of material and be incredibly heavy.  This is the number one reason why most retailers never consider making such a bag, it wouldn’t be particularly cost effective and most women wouldn’t want a bag that weighs a lot on its own because once you fill it up, it will become positively unwieldy.

Secondly, for most women’s wear designers, especially handbag and shoe designers, functionality is an after thought.  And if you care about aesthetics, you’re not going to design a bag big enough to hold all of a lawyer’s essentials unless you want to sell it in a set with a Sherpa and a yak.

Lastly, most of the bags made for functionality are designed with men in mind.  So not only are they large and heavy, they’re tough and rugged and about as dainty as a lumberjack.

This is not to say that finding a fairly attractive, women’s work bag isn’t possible. They exist, but you need to be prepared to compromise.  You will never find the perfect bag in the perfect price point.  Either you’ll have to pay more than you intended, or you’ll have to cut back on the wish list.  

Basically, this is my way of telling you that a laptop/work bag that is functional and stylish is an investment piece, and you will probably not be able to find one for less than $250.  That’s why most law grads get one as a graduation gift.

Now that we all understand the challenges presented by finding such a bag, let’s talk about some solutions.

Audrey Brera Briefcase and Computer Bag (Lodis, $318)

This is one of the widest bags that I found, at a generous 17″.  It has a padded laptop compartment, two other compartments and the exterior pocket has an organizer to keep your Blackberry, pens, business cards and assorted items in place.  It comes in red and black.  It’s also easy on the eyes. 


Hudson Diaper Tote ($280)

Years ago, Rebecca Minkoff made a great diaper bag called the Knocked Up Tote.  It was also the greatest laptop/work bag known to mankind.  Sadly, she stopped making it, nevertheless, the existence of this bag convinced me that leather and imitation leather diaper bags are an appropriate solution for the work bag conundrum.

This bag is 18″ wide and has a few internal pockets, but they’re shaped to hold baby bottles, so I’m not sure how much help they will be.  It also doesn’t have a padded compartment, but you can pick up a padded laptop sleeve easy enough.  Also, the bag is faux leather, but that keeps it light enough to carry.  And the adjustable straps are a nice touch.

Other solutions to the laptop/work bag challenge include:

A wheeled case, like the ones pilots use.  By no means ideal, but it’s not like you can leave the legal files at the office if you’re heading to court or a committee hearing.  Just get a truly fabulous handbag to compensate.  

A vintage leather briefcase.  I was absolutely horrified by what they charge for new leather briefcases ($1,000-$2,500).  So I thought, “Why not go vintage?”  

They’re less expensive, and a bit rugged, but with a sense of style that’s tough to ignore.  Plus, you can pick one up at a thrift store or on eBay for a fraction of the cost of buying new.

You can also pick up the ever popular Coach Beekman on eBay.  Why the company ever stopped making this classic messenger style briefcase is really a mystery.  I suppose they were too busy making those hideous, signature fabric patchwork monstrosities.

Alright, we have reached the outer boundary of my knowledge about briefcases.  So, hopefully, some of my readers who work in the legal profession have some more suggestions.

Also, please don’t leave a comment about how these bags are great but they’re too expensive.  As I said above, to find a stylish and professional bag for work essentials, you’re going to have to spend some money.  This is one area where it is difficult to find a cheaper option, and to get something well made, I wouldn’t recommend a cheaper option.  Truly, this type of bag is an investment piece, so save up and invest.  Just make sure to buy something classic in a neutral color (grey, red, black or brown).

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  1. Kate says:

    It's definitely not the sexiest bag I've ever owned, but I swear by my Tumi purse. It's waterproof, has more pockets than a boy scout could shake a stick at and incredibly light because it's made out of parachute material. After being let down by designer bags that haven't held up to my level of wear and tear, the warranty doesnt hurt either –

  2. Kate says:

    I've got the briefcase found here in black:

    It might not be the most stylish, but I don't think it breaks any style rules either. My laptop fits in it, as well as papers or a binder when I have to. I really like it, and although it's not something I use everyday (only when I really need to carry my laptop, or need a briefcase for interviews), over the past 3 years it's held up very well. And it's a nice price point.

  3. Roberta says:

    Epiphanie bags are designed to be camera bags, that can also hold a laptop, but they have inserts that can be velcro'ed in and out to customize what you carry with you. The bags look great, and will protect your electronics, as well as holding a ton, and being comfortable on the shoulder. I carried mine all over Manhattan one day, loaded with camera, lenses & laptop. I have the Clover bag in turquoise. Maybe if you bug owner Maile Wilson enough, she'll do straight-up laptop bags too! I also have a pretty good Clark & Mayfield bag that I got from eBags a few years ago, similar to this: It's held up well, though it can't hold that many files once you get a laptop in it.

  4. Stephanie says:

    I got the Lodis bag as a graduation present, and am packing it for a work trip as we speak. It is truly fantastic! I got it in black; it still comes with red leather detail around the seams, which makes it fun without being too bright. The one thing I would recommend with this bag, and really any large messenger/tote, go to a luggage store or leather shop and have someone punch a custom hole in the strap so it fits comfortably over your shoulder! I'm short, and had I not done that this bag would nearly drag to the ground and take me with it.

  5. MM says:

    I've been looking for a new workbag for a while – have yet to find the PERFECT one for me (the only way I can justify the cost is if it's absolutly right), but thought some of the ones I'd found might be perfect for others –

    The closest to perfect is the Kate Spade Chrystie Street Large Anisha – currently on sale during their 3 day sample sale for $189. This bag is huge, but very simple, and comes in black and camel. I actually think it's a little too big for me, but still a little tempted..

    The Tignanello Stich Tote fits a 13 inch computer – it's $118 from ebags so it's probably the best priced real leather one that I found, but I took a look at it in a store, and the stitching is a little too high contrast for my taste.

    The Daniella from Hobo International is 15 inches wide so would fit a smaller computer. It's $188 from ebags and comes in black – I really liked this one, but some of the reviews said the leather didn't last well – anyone else have experience with this one? Hobo international has a few others that might work – the Annalisa comes in balck and camel and is $248.

    LL Bean has avery large leather tote bag that would hold a ton, and a mini tote bag – the large was too big for me and the mini too small, but I'm sure the quality is great, and LL Bean has a great return/replacement policy if it doesn't wear well.

    Ebags (not to shill for this website too much, I've also found decent options on overstock and endless), also has a decent selection of this type of bag under their business and laptop section (instead of handbags) – for example, this one is faux leather, but the styling is nice and it's only $25

    Hope this is helpful to someone and my hours of “research” time haven't gone to waste!

  6. Ellie says:

    My laptop/file bag that I use is from Coach, but I got it in their men's section (well, it was a gift to my Dad, who had no need for it, and gave it to me, yay!). It isn't the most stylish, and it certainly costs a pretty penny, but I have been very happy with it. It's the crossbody leather business tote, and I have it in black, and I feel like it doesn't completely scream “I should belong to a man”

  7. Heatherskib says:

    I'm leaning more towards a second WhakSak ultimate tote for work. While they are tennis bags, they have 3 generously sized sections, carry my monstrosity of a laptop easily in the center section (which has two additional deep padded pockets and a pocket for holding tennis balls that can be used for tucking in a drink.), have a ton of pockets and organizational details. There are 2 more large zippered pockets- one on the exterior of each side of the bag, a side pocket that holds both my blackberry and my ipod touch easily, the front pocket is large enough to fit a paperback and has 5 card slots, 2 pen holders and another cell phone sized pocket. There's also the detachable water bottle holder on the other side of the bag. I have the uptown girl version- I've carried it pretty much daily for a year and it looks practically brand new. I think I might get BlackJack next.

  8. MM says:

    One more good option –
    $118, black leather, and fits a 15.4 inch laptop. Never heard of the company, but looks like they have a lot of decent looking leather laptop bags in a lot of colors in the $120-$150 range.

  9. Guest says:

    I also got the Lodis one as a graduation gift (more than 4 years ago), but sadly, it didn't hold up too well. The zippers broke (probably could be fixed). Other than that, its is [was?] a sylish and functional bag. I received many compliments and queries as to where I got it.

  10. v says:

    I picked up this bag from Ann taylor a few months ago and I LOVE LOVE LOVE it. It has two interior flaps, so the computer goes on one side, documents in the middle between the flaps, and my ” purse stuff” goes on the other side. It's not padded, but is roomy enough for a computer with a sleeve. It's sold out, but there may be some lurking on ebay.

  11. CatG says:

    I've got a Coach Felicia Extra Large Slim Leather Duffle, that I got on Ebay for about $100, in black, and loved it so much I also have a second one in gorgeous chestnut leather. What it doesn't have – multiple pockets, just the standard 3, one which zips. What it does have – tons of room, a comfy strap, a sleek design, and it's sturdy as heck. I use it for daily use and as my carry-on when traveling. here's a pic of the chestnut/whiskey one.

  12. B says:

    I realise that maybe this is not overly helpful to many, because most of you are US-based, but I have this one:, which

    a) is only sold in the Crumpler Europe store and
    b) they seem to be selling the last ones at the moment, because the choice of colours is severely down from when I bought it last November.

    I have it for a 13'' laptop in brown and it was seriously the perfect purchase. It comfortably fits my Laptop and accessories (chargers, small make-up bag, phones, cards, wallet… what have you!). It's also great for organising because it comes with lots of compartments, including a padded laptop one. Really I can't sing the praises of this bag enough. It looks modern yet serious enough for the office and I've received compliments on it from quite a few people. If you can get it shipped to the US and are happy with the choice of colours they still have left, I'd give it a thought!

  13. Rachel A says:

    I recently bought the Coach Chelsea Large Shopper in brass/british tan ($400) and its working really well. My only complaint is the thinner straps, but that's a small compromise to make for a bag that's not horribly huge. It's definitely not for lugging a ton of stuff back and forth between work and home, but for that I have a rolling bag that gets used once or twice a month. For normal commuting and court appearances, my Chelsea Shopper fits a laptop, legal pads, and several files. It's also small enough that it doesn't look ridiculous doubling as a purse when I run out for lunch with colleagues.

  14. Courtney says:

    I bought the Patent Leather Shopper this weekend from Zara, and it fits not only my essentials, but laptop and files – it has a few interior pockets, as well as a shoulder strap. It's basically the size of a small tote bag, and like the comment above, it doesn't look ridiculous if I use it for something outside of work. Plus, it's only $50! Only thing is that it does not have a full zipper closure like some might want…

  15. brett says:

    I have the McKlein USA W Series Willowbrook Leather Detachable Wheeled Women's 17″ Laptop Case and I love it. It's big enough to hold my (rather bulky) work laptop, and a legal file and the wheels zip off of the bag leaving a rather attractive briefcase (with a detachable shoulder strap) if you don't need (or want) the wheels on a particular day!! (I have found that this is an incredibly helpful feature). I have the black, which has subtle red contrast piping and I get compliments all the time from other female professionals painfully familiar with this particular hunt. The zipoff wheels earn me compliments from my Transformers-nostalgic male colleagues. It even has a little rain case that I can put over it if I get caught in a monsoon on my way back from court (also known as 3 p.m. June – August) I purchased mine from Ebags, where it is currently available for $150 in the black, a lovely red, and a questionable lime green. If I need to hold more files, I find I just need to buckle down and use a litigation case.

  16. BB says:

    Most days I can get away with a (largish) purse, and I carry a portfolio under my arm to hold handouts, documents, etc, but I do have a leather laptop bag from Franklin Covey. Sleek, black, divided pockets for my laptop and files, and a lot of organization/pockets/etc–it looks like a larger tote bag. The downside is its more than 10 years old, so a) the “cell phone” pocket will not hold my smart phone (I realize this is a first world problem) and b) you can no longer buy it on the Franklin Covey website. But while trying to find a link, I did notice some leather, somewhat attractive (for a laptop bag/briefcase) options for less than $200, so if funds are tight, check there. For what it's worth, mine has held up beautifully with occasional-to-moderate use over the past ten years.

    The corporettes really like Lo & Sons bags. Not leather, but still professional looking. I haven't had one, so I can't comment on quality.

  17. Meg says:

    I just wanted to underscore the comment above – Kate Spade's 3 day online sample sale has some great (and heavily discounted!!)leather bags that could work for this type of use

  18. Marie-Christine says:

    You can help yourself a lot by thinking around the 16″ laptop and padded compartment requirement, which is getting pretty much obsolete anyway. I just got a very nice netbook which is 12″ and super powerful, along with a simple neoprene sleeve. $400, no need for laptop specific anything else. (I got 12″ because it's a lot more comfortable than 10″ if I'm stuck with just the netbook, but that's an option also if you have docking on both ends). Throwing a bit of money at the hardware improves the commute immensely if you usually just shuttle between home and office – a large screen, full-size wireless keyboard will do your ergos, but don't forget a charger for each end (and another couple for the phone), and any necessary cables. 2lb total, ladies, think about it.

    There, you've just saved $500 on the laptop, and who knows how much more because you can buy a regular bag that's just sized to hold files.

  19. Kristine says:

    Theresa Kathryn has the best laptop bags in all sizes. They are expensive, but don't buy them for full price! Sign up for the emails and at least twice a year they have a 50% off or once eve 60% off sale. I now have 3, all purchased during the sales. They have numerous compartments, look great, and most important to me a pocket on the back to skip over your luggage handle so you don't have to carry it thorugh the airport. I travel every week for work and these hold up and look great.

  20. J says:

    I just bought this bag:

    it is wide enough to hold a redweld file with a laptop in a thin sleeve next to it, and has room for my wallet and makeup bag too. I love it – am so happy I snatched it up. I don't know if it's available in the US; I got it in the UK.

  21. elizabeth says:

    I'm no lawyer but I recently upgraded to the first decent work bag of my life when I got a high-profile temporary reassignment at work. The Fossil Vintage Reissue Top Zip Tote has been GREAT — and carries a ton. Very durable, nice leather and right at that magical rice point – $248. The zipper top was key to me because I don't want strangers peering (or reaching!) into my bag on the metro…

    18.5 × 12 × 6

  22. E says:

    To add to the Lo&Sons comment from BB, I received the O.M.G. bag as a gift for Christmas (at 40% off) and use it for commuting daily. I've been pleased with the professional look and durability plus you can wipe down nylon. My bag is black with black leather straps and silver hardware–there are other similiar professional styles available. For me, the best parts are the laptop pocket (up to 13 inches), file holder, and the separate compartment for shoes (yoga or gym after work). I've also used it for overnight work trips and it has been terrific. I would still buy at full price but watch the website for a sale.

  23. Dr. Jean Grey says:

    I own the Morena from Hobo International..I don't love the styling, but it is the ONLY thing I've found that is functional and appropriate for my job and commute

  24. CH says:

    A few years ago I got a leather Fossil tote (I think it's called the Executive Tote) in an oxblood color as a gift. It has a padded divider between the two main compartments, mesh pockets for laptop charger/other computer-y bits, an inner zip pocket, and four outside pockets. Top zip (non-negotiable). It's fits my 13″ laptop, a file or 2, and purse essentials. The straps aren't the most comfortable, but I don't have to carry a laptop every day so this works well for me. It's also a decent travel bag.

    If I need a ton of stuff, I have an Ellington Lucia Weekender that works as a laptop bag (I put my computer in a padded laptop sleeve first). It's bare bones and not super-stylish, but it will hold all your work stuff including computer, files, an extra pair of shoes, and a lunch. And like the name says, it can fit everything I need for a weekend away. It has a ton of pockets and is coated nylon, so it's not too heavy.

  25. Allison P. says:

    Apple has great bags on their website. The Kate Spade ones are perfect for work!

  26. HB says:

    My father bought me a wonderful, functional bag from Levenger (there is a shop in the Tyson's mall, for those needing to touch) for graduation. I call it my lady briefcase. It is not exceptionally stylish, but I get complements on it all the time. It has many pockets and is three compartment on the interior. It does not have a padded compartment for a laptop but will fit a padded laptop case and files if necessary.|Level=2-3-4|pageid=8593

  27. Stacy says:

    Cole Haan has the best work totes. I'm not crazy about the colors they're offering right now but my favorite work totes ever have been from Cole Haan.

  28. espie says:

    I know this sounds crazy, but try Staples! I got a great, mostly leather bag that holds a 14″ laptop and has a zipper on one side of the bag that can accomodate large files for busy days but remain an understandable size on others. I needed something other than my canvas messenger bag and collegiate backpack for an internship, so I wasn't looking to spend a lot.

    While it is not the most fun bag, it comes in espresso and black, has good shoulder straps, zippers to shield from water and has a nice white top stitch detail. It retails for a little more than $100, but if you wait for coupons or the 20% off bag, it does go on sale, I got mine for $70. Of bags I've owned its held up through many days, trips and gratuitous use for the last two years.

  29. Whitney says:

    Levenger ( has cute ones!

  30. n says:

    @Allison P — love the Kate Spade bags! has one version at half the price it is on the Apple site:,default,pd.html

    Part of my solution has been to get a smaller laptop! I couldn't live without my netbook. I recently bought a Longchamp Roseau bag to be my work tote. The downside is that there's no shoulder strap. I love that it is classic, sleek, and understated, while still feminine.

  31. R says:

    Coach's Men's Crosby Leather Business Tote looks pretty awesome for work but $550? Ouch.

  32. katarina says:

    I use my black Longchamp Planetes Tonal to take files to court. I can get a redwell, laptop in a sleeve, cord, charger, cell phone, make up bag, snacks because god knows I probably won't have time for lunch and will be eating a granola bar in the bathroom (ew, TMI but true sometimes), and all of the other shit I carry around. This bag is my life and it looks more professional than the brown strap, regular longchamps.

  33. A says:

    I second the roller-bag suggestion Belle. As someone who has worked as both a lawyer and a staffer I was always on the look out for the perfect tote bag and even invested in quite a lovely one. However, being sent to my home state for a couple of months meant family got a chance to see me in my work clothes. My mom discretely pulled me aside to point out that briefing books+copies of legislation/case files case books legislation as well as a computer and personal essential made my shoulder tote so heavy that my suits (regardless of material) were always rumpled on that side and I had a near permanent headache from the uneven load. A roller bag and a parental gift of an Oroton handbag for my personal essential to “incentivise” using the roller bag (let's face it they aren't pretty) have me looking better kept and feeling it too.

  34. Cindy says:

    I'm an IT consultant that travels a LOT, I got tired of constantly buying new bags for my laptop, so I finally got a Tumi laptop bag. It is not the cutest bag ever, but for me I had to sacrifice style for functionality. I never thought to look at diaper bags though!

  35. D says:

    I love the Lodis bag.

    Belle, have you seen this monstrosity?

  36. Whitney says:

    Putting in my vote for Levenger as well. Great quality leather goods…I have owned two Levenger wallets and they are terrific.

    Here is the link to their Majorca Briefbag:|Level=2-3-4|pageid=6631.

  37. LJ says:

    I have a Coach diaper bag and I swear by it! I got it as a sophomore in college and have used it daily through my final year of law school. I finally broke down and had it professionally cleaned, as after 5 years of daily use, the leather and fabric were in need of a wipe-down. The hardware and fabric has held up exceptionally- no rips, no tears, etc! 5 years of continuous use- impressive!

    It has enough room to hold my netbook (small-ish laptop), many files and a binder or two. It also has great internal pockets (two zippered ones which run the length of the bag, one snap-enclosed one which runs the length of the bag, plus a cell phone pocket and three pen slots). It came with a changing pad which I thankfully have not needed to use yet- but it allowed me to justify the $400 price tag as an “investment in my future”.

    You can sometimes find these as at the Coach outlets and their most current version can be found online here

  38. Michelle says:

    I work for Coach part time and agree with Belle..the signature bags hurt my eyes. So heartbreaking to see someone come in and throw away $300+ on such an ugly product. If you look on the men's section at there are several good options for a work/laptop bag. Two of my personal favorites are the Crosby Leather Business Tote and the Bleecker Leagacy Leather Weekend Tote that is actually 21″ in length. Not trying to sell anyone..we don't work on commision 🙂

  39. A says:

    When I was a campaign staffer I swore by using a work appropriate diaper bag. The changing roll is a lifesaver when you end up sitting on the floor of some high-school gym or airport trying to get a document finished asap. Similarly the bottle holders allow you to make sure you are never without water without worrying about important docs getting ruined.

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