The Best Bags for Walking to Work

the best bags for walking to workWhat is the best bag to carry if you walk to work? Reader A wonders…

I’ve had a bag dilemma for years and though this venue might provide a solution. I thought perhaps someone out there might have found the holy grail of bags to address the following issues, and I’m sure others are looking for the same. I would certainly love a post on this. I’m a lawyer and I walk almost two miles to work everyday. Here’s what I’m looking for:
– Big enough to carry folders, papers, occasional laptop and occasional change of clothes
-Color-neutral enough to be worn with anything for everyday use
-Professional looking
– Comfortable to carry long distances, such as a cross-body style with comfortable strap. Maybe a backpack style?

Does such a bag exist? I sure hope so.

I’ve always loved walking to work, and I’ve regularly schlepped about that distance. While there are so many benefits to walking to work (fresh air! clear head! some exercise!), I do feel like I’ve done some serious damage to my body from walking so much. For example, whenever I get massages, the masseuse always comments on the huge knot on my right upper back (where I usually carry my bag), and I honestly blame the first few years of walking to work (back in the days when I wore Steve Madden 3″ stacked heels regularly — for the 2 mile commute!) for the feet problems I have now. (I suppose there’s another post idea there, but my secret belief is that feet problems are like dreams: no one else wants to hear about them.) So: I gotta say that Reader A may be asking for too much. A laptop? A change of clothes? This all seems like a lot for a regular commute, and probably the smart advice to her is to find another means of transportation if she has to carry so much. That said, on the rare occasion where I wanted to carry a computer or a change of clothes, I suppose I could have fit a super-lightweight, small laptop (like my netbook) into my bag, and I also could have possibly fit a pair of jeans (for a night out) — but not both, and certainly not with a change of shoes.

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Cole Haan - HW Parker Medium Hobo (Greige) - Bags and LuggageFor the past few years my bag of choice has been a large hobo. I’ve found that a single strap is a must (it stays on your shoulder better than two straps), and a good bag that has pockets keeps your phone, ID/subway pass, and lipgloss close at hand. My all-time favorite is a Cole Haan hobo (I have 3 or 4 of these — I had to put a moratorium on myself! They’re all similar to the “greige” one pictured (also available in plain black), but I also like my Kooba hobo (similar to this one, pictured, Kooba – Alexander (Berry)), and my Rebecca Minkoff hobo (Rebecca Minkoff – Nikki (Red) (not pictured)). They generally fit all the stuff I keep iKooba Alexandern my bag, with space for an extra pair of shoes if I need to carry them, or perhaps the laptop/change of clothes that Reader A is dreaming of. Keep in mind, I’m not saying this is the smartest choice — I’m just saying, this is the kind of bag that I found worked best for my commutes.

LeSportsac - Deluxe Everyday Bag (Fly Away Black) - Bags and LuggageIf we’re talking smart choices, though, you probably do want a crossbody or a backpack, to better distribute the weight; you might also want to look for a lighter fabric bag (such as a nylon) instead of the leathers and canvases that I always prefer. I might point you to a LeSportsac Everyday bag (pictured), which has been my gym bag for years, and is now my favorite diaper bag. I vastly prefer my leather hobos for style, but the Everyday bag can’t be beat for being lightweight and well organized. I might also point you to the Marc Jacob nylon knapsack — it’s pictured at the very top of this post in pink iris, but it’s also available in black. LeSportsac also makes a nylon backpack, as does Tumi. My personal $.02 is that fashionably speaking, the backpack is kind of at the bottom of the pile — but sometimes you have to be kind to your body and prioritize comfort above fashion.

Readers, do you walk to work?  What bags do you carry?  Have you developed any “best practices” for commuting?

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  1. Rickshaw Girl :

    I had exactly this dilemma. Exactly. Now I love my Rickshaw commuter messenger bag (from Rickshaw Bagworks, in SF). It fits everything I need and is comfortable for my long walking commute (great straps and fit), and it holds its shape more / looks more professional to me than the timbuk2 bags that I see everywhere. Not high fashion at all, but it feels equally at home on the bus and in court / client meetings. They also make bigger ones, and backpack models.

    • Anonymous :

      Second this! When I read the post, I had to comment to recommend Rickshaw. I received one large enough for a laptop and two casebooks while I was in law school. The strap is padded and adjustable in front and back, making it comfortable for carrying heavy and light loads. It’s made of a cool plaid raincoat fabric and, four years later, still looks brand new. Highly recommend.

    So, I made it through the “working interview” (which was awful and weird) and they offered me the job. While I was able to negotiate up from their lowball offer, I only lasted one round of back-and-forth, caved and accepted a much lower salary than I wanted for the first 6 months. In hindsight, I think I could have gotten a better deal. But at least I’m not unemployed anymore, right :)
    Throughout this process, I have gotten the distinct impression that this firm is aggressively unprofessionally cheap by default (i.e. they wanted me to stay at a family member’s house during training so they wouldn’t have to pay for a hotel room… I told them that it was too far away and I needed a room, they agreed to pay for a room for the first half of training and then “we’ll see”). So, I am concerned that they will try to pull stuff like that throughout my training period and, because I am working from a virtual office, try to shove costs off on me.

    So, I am considering sending the managing partner an email to “clarify” my assumptions underlying acceptance of the offer… i.e. they will pay standard per diem while I am in training, they will provide or pay for all equipment needed for the virtual office, they will give me health insurance and 401k in 90 days (rather than the 6 months he mentioned). Any tips on writing this so I am not presumptuous? I don’t want to discuss it over the phone, both because I want it in writing and because I am likely to get snarky. Do you think they will rescind my offer?

    I so want to be employed, but I don’t want to get screwed!

    • associate :

      I think an official offer letter with the terms of employment is pretty standard. If they didn’t send you one, I’d think what you laid out is fine. If they are going to rescind your offer for writing a letter like that, maybe it’s better to find out now anyway.

      So….what did the “working interview” entail?

      • The offer letter only touches on salary and the training requirement. I am feeling uncomfortable about the other conditions because they seem to be nickel and dime CHEAP CHEAP CHEAP.

        Ah, the working interview. They flew in 3 candidates for the same job. Two male interviewers, the other two candidates were male. First, they sat us down and chatted (i.e. the guys talked about sports). Then they had us take a typing test. Then, they gave us a mock case to prepare. Lunch (where the guys talked about sports and their wives/kids the entire time). More prep time, then we argued the mock case against each other… since there were 3 candidates, each of us had to go twice (argue the plaintiff side and the defendant side).

    • Congrats! I would send him a short, nonconfrontational email saying that you are looking forward to your new job and that you would like confirmation that the following will be made available to you by employer, then list all your expectations (succinctly and nondefensively). If he says no and they are major things, you can say that you had agreed to the salary he proposed under the assumption that employer would also provide these things, and if employer will not, then you need a salary increase of $X to compensate.

  3. I mentioned this above, but want to suggest using two totes as needed. I use both a smaller, laptop + clutch sized bag (it also holds a small amount of papers, if I don’t have much work to bring home). I augment that with a nylon shoulder bag if I’m bringing home binders / taking home a bunch of shoes I left under my desk / etc. I like spreading the weight over both shoulders, but dislike the feel of a backpack (always feels like I’m shoving my chest out at the world, plus they wrinkle clothes badly!)

    Kat, don’t act so shocked that someone might carry a laptop every day! I prefer to take my work home to finish once “face time” is over for the day, and even if I don’t have anything to take home when I leave, it’s better to carry the laptop home and NOT get the surprise email than vice versa :)

  4. Although I generally don’t like bags with brand logos, I carry a LV Neverfull (the largest size) to work every day. I walk about a mile each way, and it is the perfect bag for what I need. I can throw my lunch, a pair of shoes, my laptop, files and whatnot in the bag. It has a smaller pocket where I can keep my building key card, keys, etc. The bag is lightweight and the shoulder straps are thin so they stay on my shoulder perfectly. I have narrow shoulders, so most bags slip off. It also looks more professional than a messenger bag.

    I love how it can fit anything and still look stylish. You can expand and shrink the sides depending on how much you’re carrying each day. Its been working out so great that I now use it as a diaper bag on the weekends because I can throw in all of my son’s extra clothes, food, diapers, toys, etc. and still have room for my wallet and sunglasses.

  5. Personally, I love a convertible backpack, like this one from Mosey (which I got recently and adore): . It can be carried like a satchel and reasonably resembles a regular (if big) handbag, but is also immediately available as a backpack with no fussy clipping and re-clipping of straps. It’s a great airline carry-on for work travel for those reasons, too.

    • I really like this bag! Two questions, though: (1) Are the straps comfortable when you use it as abackpack? (2) Does the top securely close? (It looks like kind of flimsy closing mechanism, plus I’d be worried about rain, etc.)

  6. SoCalAtty :

    I’m a little bit of a gear person (ok, a lot) so I have tons of bags. REI carries backpacks and messenger bags with laptop sleeves, and currently they have several, like the ones from Thule and Keen, that are black and streamlined and would be comfortable and not too obtrusive to take even into court.

    Just use the search features on REI’s website under “travel.” Their return policy can’t be beat…if you hate it, even a year later, they’ll take it back. Their prices are usually list price, but the customer service and return policy make up for it.

  7. I have one that is very tolerable for long-range schlepping, a huge Clava leather tote. (link below). It’s very lightweight for leather. But the most important features are that it’s huge and that it has long, padded straps. Padded straps make such a difference! And the length really helps too. I can fit a smaller purse, legal-size files, shoes, and gym clothes in the bag with no problem. Laptop would also fit.

  8. Pink on Black :

    Dealing with this issue too. Just started commuting by public transport as my office moved into SF city from the Peninsula and realised how stiff my back has gotten from the trek (1.5miles each way to the train station). I’m going to try out a trolley, just bought this the Conair compact cart from Amazon. Was definitely also eyeing the McKleins. Thanks for the other suggestions, I’ll look into them if using the cart isn’t as easy as hoped.

  9. Diana Barry :

    2 miles each way w/ laptop and extra clothes???? BACKPACK.

    I commuted for 4 yrs, 2 miles each way (Boston) with a Patagonia women’s backpack. It was awesome. I kept a purse in the office for when I went out to lunch or meetings.

  10. Perhaps not suitable for the OP’s requirements, but I just transitioned from handbag to using a pouch (the American Apparel pouch to be exact). Here’s my thinking: wearing any shoulder bag brings my back and body out of alignment, esp on my dominant side. Carrying a pouch is better for biceps and forearms because it can pretty much act as a weight (like a dumbbell). The AA one comes in 3 sizes and is real leather (I’m sure there are vegan varieties for those so inclined). Although now that I’ve upped my gym sessions per week, I pretty much am back to heavy tote.

  11. Wheelie bag.

  12. I walk a couple miles a day and carry books, files and sometimes a laptop. I found a cute grey plaid flannel backpack at Target. It’s very comfortable and was less than $40.00, as I recall. As long as I take it off before entering the building, I don’t care if I look a little dorky.

  13. cheap lawyer :

    These bags with wheels are reasonably priced:
    Not leather, but more personality than many court/litigation bags.

  14. I searched forever (and spent many a day lugging around three bags) before finding the amazing Alesya laptop bag – gorgeous leather, stylish, super comfy strap, room for a 17″ laptop plus all the cords, etc. I no have to haul a laptop back and forth to work, but I love it so much I continue to use it everyday to carry papers, my wallet, umbrella, my lunch, my work shoes, etc. Amazing how much fits in here.

    • Ah, love those! No fair linking to something awesome that’s sold out. ;)

  15. A used a cross-body bag throughout law school and always studied at home or my favorite coffeehouse, and at first I had definite pain on the right side from carrying the bag on only one side.

    Then I forced myself to learn to feel comfortable with the bag also being carried on my left side. Eventually, I played a little game with myself where I divided each day’s route 50-50; half the time I carried the bag on my right side, and the other half on my left side! It really helped.

  16. I like messenger-style bags especially ones by Fossil. Using a backpack makes me feel too much like a student, and was also causing lots of pressure on my shoulders and back.

  17. I hate to be the unfashionable one, but ladies—you should never carry more than 10% of your body weight on one shoulder (i.e., no more than 20% if you’re double-strapped). If you’re a small woman, this might mean that you shouldn’t carry more than 10 pounds on one shoulder. 5 lbs for laptop, 300 sheets of paper (3 lbs), a pair of shoes, and the weight of the bag itself and you’ve already hit your limit—not even counting keys, wallet, phone, makeup, and anything else you might want to carry. I used to do this, and nearly caused myself permanent back damage.

    Dakine (dakine dot-to-the-com ) makes some good, durable backpacks, some of which are quite nicely sized for women. I have a fun, brightly-colored one that fits my 5’2” body perfectly (very necessary, because I bike). They also have more staid versions, for both men and women.

    Chrome (chromebagstore dot-to-thecom) and Timbuk2 make high-quality messenger bags, typically with extra body straps.

  18. Collins_JCC :

    the best solution i have found is a kate spade diaper bag…minus the changing pad. it has tons of space and different pockets. it also comes in crossbody styles!

  19. I love my bag from

    They are very well made and lightweight, and you can fit almost ANYTHING in the large bags!

  20. I do the 2 miles to work as well – and I have always used a lululemon bag and take all my gym stuff as well as lunch with me to work. Their bags are great at compartmentalizing, and can be stylish enough to pass for a proper purse. Usually I keep a mini bag inside for lunchtime errands.