Updated: Jan 25, 2019
I love to walk downtown in any city I go to. The skyscrapers tower above and men and women in suits flood the streets. Unfortunately most are rocking 1980's tailoring, perhaps others stretching the life of their garments well past the "expiration date". Though each of these cases are cringeworthy, none make me cringe more than when I see a true gentleman of style wrinkling his well-tailored high-quality suit with a techy looking backpack. I warn you, do not ever pair a suit with a backpack.
When a gentleman dresses with intent and finesse it is obvious. Perhaps this same gentleman has even paired an elegant heirloom watch with his business suit. The sophistication and timelessness of this effort is immediately lost when the same man reaches for a shabby looking bag.
Make sure when you're in this situation your chosen bag matches your outfit, and conveys the same message of elegance and class. As with any quality leather piece, investment in a proper leather bag will show excellent return on investment over the years. A leather messenger style bag or briefcase should be the only consideration when also wearing a suit. Just as with any piece, wardrobe fabrication principles are key. Avoiding distressing or cheap looking embellishment will ensure that the leather bag you choose will age gracefully with you, growing more soft to the touch and developing a fine surface patina. Details like brass hardware and sturdy riveting will be well worth the premium paid in the beginning.
Remember, everything on a man's person becomes part of his message to the world. Dress with intent. Dress with confidence. Do not let sloppy accessory choice undermine all your hard work.