Choosing the right bag doesn't have to be confusing and intimidating.
According to Oliver Cheshire, “when it comes to choosing (one), there are two things you must think about - function and fashion, and always in that order. Function must be by far your primary concern. But it must also look the part and work for almost every occasion.”
Whatever your criteria, there are several questions I always ask myself when shopping for a bag:
Does it work with my sense of style?
Choose a bag that matches your aesthetic. You want a bag that will match the outerwear in your wardrobe. No sense in buying a whole new bunch of clothes just to match your new purchase. The bag should enhance your current style, not fight it.
Will it suit my needs?
Picking a bag that is fashion forward and cool but with nary a chance of holding all your daily stuff is not a very wise choice indeed, especially if you’re going to be splashing a substantial amount of cash on it.
Is it going to be used as a day or a weekend bag?
I generally categorise my bags according to the above.
“Day” bags include backpacks, satchels and briefcases, and further broken down into work, gym and casual bags. I tend to gravitate towards the leather variety as they are a little more suited for the work environment and never fail to add sophistication to an otherwise plain outfit.
Casual bags crossover into the “Weekend” category, along with duffels, and they can be a little more relaxed.
At the end of the day, you are buying a bag for yourself so pick one that works for you. There is a plethora of styles out there and there will be one that ticks all your boxes.