The Gentleman: Lagniappe – Ditching the Backpack

About a week ago, I had a realization that no sartorially savvy gentleman wants to have… I looked absurd. I was walking to work in a neatly pressed suit with a crisply folded pocket square and an impeccable tie when I looked into one of the reflective windows and couldn’t believe my eyes. I was wearing a blue JanSport backpack. All of the hard work I had done (and blogged about for a few months in my Suiting Up columns) to perfect suiting outfits was completely ruined by a backpack I had been using since the days I was stuffing it into my locker. Ever since that revelatory moment, I have been on a quest to find a new bag.

I have yet to arrive at the point in my career where I would want to carry a briefcase. Instead, a messenger bag seems like a good alternative. It’s smart and clean enough that it can be worn over the shoulder with a suit, but it’s still rather casual so that I can schlep it to class for my last two years of law school.

My online research produced three different styles of messenger bags that I think would work well for my purposes. I imagine that many young gentlemen are facing a similar challenge, so leave a comment letting me know which you think works best for this kind of student/semi-professional situation!

Photo Credit: Jack Spade

One of my good friends in New York has this bag from Jack Spade. It’s made of nylon and canvas. I like its sleek, clean, modern look. My friend is in the arts and wears the bag very well, and while I think that it would be professional enough in a law environment, but it might be a bit too modern for my taste.

Photo Credit: J.Crew

J.Crew has a cotton/canvas messenger bag priced under one hundred dollars. I like the buckles on it much more than the zipper on the Jack Spade bag. It’s got a nice weathered look but might be a bit too casual to bring to the office or even to class. I think that if I were a few years younger and an undergraduate, I’d go for this, but I really can’t see myself slinging this over the shoulder of my suit.

Photo Credit: J.Crew

When I saw this bag, advertised as J.Crew’s Leather Artisan bag, I fell in love with it. The color and the weathering are perfect; the only problem is the $225 price tag (despite the fact that it’s one of their first fall catalog items to go on sale). J.Crew has a 15% discount for students who show their college IDs, which would bring the bag to under $200. This may have to be a splurge purchase this fall.

As you may have noticed, an old fashioned leather messenger bag is definitely what I’m searching for. Leather is classy enough to be worn with a suit but has a great rugged quality so that it doesn’t look too formal at school. You can even use it as a travel carry-on bag! If $225 is too much for you (or me, for that matter), there are a couple of options. Kenneth Cole sells a similar leather messenger bag for under $100. It doesn’t have all the antique details of the J.Crew bag, but has a similar overall look.

Photo Credit: Kenneth Cole Reaction

Another option would be to find an actual vintage messenger bag on Ebay or Etsy. I sort of like this idea. I’ve always found something a bit blatantly commercial and fake about buying clothing and accessories that are “faux vintage.” Buying an old, roughed-up leather messenger bag, applying some polish to it and taking it on some new adventures sounds kind of romantic to me. Perhaps this will be the route that I will take. I’ll be sure to write another post in a few weeks about whatever I chose.

Next week: the Gentleman previews some of his favorite stores’ autumn collections…



Filed under The Gentleman

5 responses to “The Gentleman: Lagniappe – Ditching the Backpack

  1. Leather – always go with leather. Synthetic materials are fine for the beach, but for the office? You need an animal. Pop into a vintage store and see what you can find. You want your shoes to be shined and looking new, but your bag to look like it’s weathered the storm. Vintage in NY means nothing, pricewise, but elsewhere you should be able to find some pretty sweet deals! Keep us posted on what you find!

  2. I think a satchel on a man is an incredibly distinguished look. My favorites have to be either the linen or leather JCrew options. I feel the linen could work more in the summer, but the leather could be a very classic bag to keep around for years.

    Look forward to seeing what you find!


  3. Just found your blog, loving it! I am looking for a bag for my boyfriend to use in medical school (an upgrade from that darn backpack he uses) and the Jcrew bag is just right 🙂

    xo Lynzy
    Come enter my giveaway!

  4. Jing

    I’m surprised you’ve just realized this. I converted my boy cousin years ago from a backpack to a messenger bag. Backpacks really should be left in high school.

    I looooove the Jack Spade, but if you’re going for something more conventional, I absolutely adore the Kenneth Cole as well. Love the design on the J.Crew one, but not so much the color. And it pops a bit with a dark suit.

  5. The Gentleman

    Thanks for the thoughts, ladies!

    Becoming stylish is an eternal process.

    I’m liking the J. Crew leather bag a lot. Will post pictures of whatever I end up purchasing.

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