Spring Sale Going on Now

20% Off Sitewide


Choosing the Right Briefcase: A Guide

jackson wayne esq. briefcase

by Dave Johnson

Sometimes it takes an agonizing amount of time to decide on a large purchase. Heck, it takes me forever just choosing the right type of bread. Have you been down a bread aisle? With large purchases that have multiple options and choices, it can be even harder. Buying the wrong loaf of bread—yes—might crush your day (#dastruggle, am I right??), but spending a lot on a briefcase only to find out that it doesn’t fit your style or lifestyle or needs is a bitter pill to swallow. And we’ve all been there, of course, which is why it now takes us fifteen minutes to decide on the cost/value difference between six-grain and nine-grain bread. Fool me once…

So Many Choices in a Briefcase

If you are looking for a good briefcase, I don’t envy you. With all the choices, it can take months to narrow it down to something right for your needs. How big does it need to be? How much can you spend? What color do you want—or need? Is it high quality? What’s the dress code or formality? What style do you like? It’s a lot to take in. And on top of all that, even if you did buy a good bag, it might not fit you. And like a pebble in your shoe, that tiny knowledge nugget of knowing you spent a lot on a great bag that doesn’t fit you will eventually annoy you to no end. (This is starting to sound like a personal therapy session.)

I hope to help you answer many of those questions. I will be pointing to Jackson Wayne as your first choice, and I hope you do consider them first, since their quality, style, selection, and value are unparalleled. Even so, if Jackson Wayne doesn’t have the right bag for you, this guide should still be valuable to you. If anything, just tell others to try Jackson Wayne first.

Bag Size

First: size. After all, you are buying a bag to store stuff. What will you be using it for? If all you need is a great briefcase for your laptop and papers, something smaller like Jackson Wayne’s Nashville Briefcase may be perfect for you. If you find yourself carrying a little more, consider the Postmaster Messenger Bag (Height 11.5", Width 16", Depth 5"). And if you carry a lot day-to-day, go with the Esq. Briefcase (Height 12", Width 17", Depth 6"). Another thing to consider is your body size. I know a guy who is 6’6” and most bags look like tiny purses on him. When he needed a bag, he had to go with the largest one available. He could find a use for the extra space later.

What Do You Actually Need? 

The other major question to answer is: what do you need? Define that before considering aesthetics or cool factor. Years ago, I almost bought a popular leather briefcase because I thought it was cool. But it didn’t solve a problem—I didn’t need it. I’m glad I didn’t buy it. Look at what you realistically carry every day, and ask how a bag or briefcase might help you. A briefcase might help you carry more, but is that good or bad for you? Also, since convenience is what you are ultimately trying to achieve, look at the inside of the bag, and see if there are organized pouches that are laid out well and easily accessible.

Maybe you have a specific use for your bag in which a traditional briefcase couldn’t help. My wife is a teacher, and she totes books, homework, and papers home every day. Sure, a briefcase would work, but what she really needs is a tote bag. She literally only needs a bag with a handle. Maybe you enjoy a good cocktail or drink with friends, and you find yourself carrying unwieldy bottles every week. You might need Jackson Wayne’s Bourbon Bag, which can carry up to three tall bottles in the main compartment and two pint-size bottles on the sides. So, consider your specific use, and find the appropriate bag for you.

Quality - So Important in a Briefcase

One of the most important considerations in your journey: quality. What type of leather is it made of? What is the stitching and hardware like? How long will the bag last? Jackson Wayne prides themselves on their impeccable quality, from thick, full-grain leather, solid antique brass hardware, and heavy-duty bonded thread. It’s safe to say this will not be an issue when considering Jackson Wayne.

Colors and Aesthetics

Let’s talk about colors quickly. In the world we live in, appearance matters. Take time to think about what color bag you want. In general, the darker the color, the more formal it is. Take the most formal occasion, a funeral: black suit, black shoes. Business meeting: navy or charcoal suit, brown or black shoes. Business casual, lighter colored clothing, lighter colored shoes. Casual: anything goes—except for socks and sandals, you monster. When using this bag, what formality of dress will you be wearing? If it’s formal business, consider Black. If it’s just jeans and a t-shirt, Saddle Tan is perfect. Or if it’s somewhere in between or a mixture of formalities for your usage, Vintage Brown is perfect. Just think of it like your shoes. What color shoes work best with your outfit? And if formality is not an issue, what color clothes do you wear? Your color of bag should probably be similar.


I hope this small guide helped you. Value is always one of the most important considerations, and buying something high quality won’t be cheap, but some choices carry more value than others. I think Jackson Wayne has, by far, the best value for your dollar, all things considered. And they have a great range of products that make sense and are easily understandable. But regardless of your choice, if you answer all these questions beforehand, finding the right briefcase or bag will be immensely easier.