How to Wear a Messenger Bag

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Messenger bags are an option for people who want something less casual than a backpack and less formal than a briefcase. They can be great options for professionals, students, and especially bike or motorcycle riders. Whatever reason you choose to use a messenger bag, they provide ample storage and easy carrying for the items you need on a daily basis.

Method 1
Method 1 of 3:

Choosing a Bag

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  1. 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.
  2. 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.
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  3. 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.
  4. 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. [1]
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Method 2
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Casual Wear

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  1. 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. [2]
  2. 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.
  3. 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. [3]
    • 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.
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Method 3
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Dressy Wear

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  1. 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.
  2. 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. [4]
    • 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.
  3. 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. [5]
  4. 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.
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Expert Q&A

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  • Question
    Are messenger bags out of style?
    Taissha G. LaReau
    Wardrobe Consultant & Stylist
    ​​Taissha G. LaReau is a Wardrobe Consultant & Stylist based in Albany, NY. With more than three years of experience, Tai specializes in helping people maximize their wardrobes by creating functional, everyday outfits that are tailored to their lifestyle and make them feel polished. While she offers virtual and in-person closet editing, personal shopping, and outfit creation, she also has a knack for helping people shop strategically, discover new brands, and experiment with new styles. Taissha holds a BS in Marketing from The State University of New York College at Oswego.
    Taissha G. LaReau
    Wardrobe Consultant & Stylist
    Expert Answer
    Not at all! If you're heading to the office, mix in some professional pieces with some casual ones to create a relaxed look. For instance, you might wear pull-on pants/trousers with a pair of leather sneakers for a polished, professional vibe.
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      References

      1. ↑ https://www.outdoorgearlab.com/topics/travel/best-messenger-bag/buying-advice
      2. ↑ Taissha G. LaReau. Wardrobe Consultant & Stylist. Expert Interview. 31 January 2022.
      3. ↑ https://www.outdoorgearlab.com/topics/travel/best-messenger-bag/buying-advice
      4. ↑ https://www.fashionbeans.com/article/common-mens-bags-mistakes/
      5. ↑ https://www.fashionbeans.com/article/common-mens-bags-mistakes/

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