How to Wear a Messenger Bag

Choosing a Bag

Pick a classic style for casual situations or a briefcase style for formal affairs. The appearance and typical materials of classic messenger bags make them the perfect match for casual dress, while the briefcase style mimics the formality and professionalism of an actual briefcase. Other styles such as vertical and military bags can be great substitutes for the casualness of the classic messenger bag.

Select a professional leather bag or informal canvas bag. Most messenger bags are made either with canvas or leather. Leather bags tend to be more expensive and formal. Canvas bags are much cheaper and more casual. Faux leather can be a cheaper option than leather bags, but still provide a formal look. Nylon bags provide an alternative for those that do not like the look of canvas.

Choose a bag size that matches your body type. Your body size should be the deciding factor when choosing a bag size. However, you also need to consider what size load you will normally carry, if this will include a certain sized laptop, and what you believe your personal style is. Larger bags tend to work better for larger frames and smaller bags for smaller frames. Make sure to measure the width of your laptop before choosing a bag.

Pick features such as Velcro for quick access or clasps for secure closure. Velcro allows students and professionals quicker access to the items they need, while clasps assure secured closure for bikers and motorcyclists. If you are a biker, you also might consider getting a waterproof bag for bad weather or a bag with reflective patches to make you more visible in traffic. If you are a student, you might want to get a bag with laptop protection or multiple pockets for more storage.

Casual Wear

Use a canvas messenger bag when wearing t-shits, jeans, or cargo pants. Canvas messenger bags are the most typical type and thus perfect for any casual situation. They are ideal for going to get coffee or running errands. Likewise, they can be great for carrying passports, tickets, and other important items on vacations. You might try canvas bag as a substitute for a gym bag. Make sure to use smaller canvas bags for vacations as you will not want something bulky when site seeing. A button-down shirt or some knitwear can also go well with a messenger bag.

Wear the strap across your body to mimic the casualness of a backpack. The intended way to wear a messenger bag is with the strap over one shoulder and across your body. Decide which shoulder is most comfortable for you. Sometimes messenger bag straps are meant to be worn a certain way, and thus the choice will be made for you.

Rotate to your back while riding a bike or motorcycle. If you are riding a bicycle or motorcycle while wearing the bag, you will want to rotate it to your back. In other words, you should wear it like a backpack. This will keep the bag out of your way while riding, and thus make riding easier. Make sure the strap is tight so it doesn't clap around when riding. Don't carry too much when riding as it is more strenuous and won't conform closely to your back.

Dressy Wear

Opt for a leather messenger bag for professional spheres and school. The leather briefcase style gives off the same formalness of an actual briefcase and shows you are ready for business. Or, the classic leather bag portrays a more casual seriousness that students will find ideal. Either way leather is the desired material in formal situations.

Choose a neutral colored bag to match as many outfits as possible. For those beginning their collection of bags or those buying one multipurpose bag, choose a neutral colored bag to match as many outfits and styles as possible. The most neutral colors tend to be black, brown, and grey. If choosing only one bag, go with a black bag, as it will easily blend with most outfits. If you want to be more stylish, try using your bag to stand out as you would with jewelry or a unique tie.

Select a bag with fewer pockets on the outside of the bag to appear more chic. If style is more important than practicality, choose to go with less storage options on the outside of the bag. The less pockets and clasps the bag has, the sleeker the bag will appear. Also, most messenger bags will have enough storage inside the bag.

Wear the bag to the side or carry it by its handles to appear more professional. Wearing the bag over one shoulder or carrying it by the handles makes it seem more like a briefcase and thus more business-like. When wearing it over one shoulder make sure the strap is pulled tight to your body so the bag doesn’t flail around. If carrying the bag by the handles, make sure to take the shoulder strap off so it doesn't flap around and cause clutter.