Style Q&A: Advice on Bags, Looking Like Magazine Models, and Wearing Rings

Grant answers your question regarding briefcases vs. messenger bags, brightly colored driving loafers, wearing clothes as good as a magazine model, button down collars with ties, and the rules for men and rings.

What should I do in the way of a bag? A messenger bag seems to casual for a suit, a briefcase feels overly formal and a man bag doesn’t really allow you to assert any kind of formality.

So my question is what should I use as a bag?

- Ollie Judge

Why not have all three and have your needs met from formal to casual?  Many men make the mistake of thinking they only need one bag.  Women may go overboard with their bags and such, but we gentlemen could take a hint from our girlfriends or wives on this one.  Having more than one bag is just as necessary as having more than one tie or more than one pair of cuff links.  Bags are considered accessories and therefore you shouldn’t limit yourself to just one.  Try brands like Filson, Jack Spade, or Tumi.  I have bags from Tumi, J. Crew, and Wilson’s Leather.  They range from casual to business and I use them all.  You’d be wise to do the same.

I really like driving loafers. I have a pair of brown leather Steve Maddens that are good standards to have. However, in preparation for the upcoming summer I would like to get a few pairs in summer colors (red, powder blue, etc…) but I feel like spending $400 on a pair of Tod’s Car Shoes is not a reality for me. Are there any less expensive options? I’ve been looking online and can’t really find anything. Thanks for any advice you can offer.

- Albert (from Philly)

Driving shoes and loafers are great casual shoes for the Spring/Summer.  If you’re brave enough to branch out into different colors I salute you.   However, most reasonably priced retailers will only have the standard black, brown, and navy.  Try Florsheim by Duckie Brown.  This collaboration between old and new has highlighted by shoes that look like highlighters.  Try magenta, ox blood, or turquoise.  For $175 they’re a stylish and affordable addition to your footwear collection.

Seriously, why don’t my khaki pants look as good on me as they do in Esquire?

- Matt S.

1.  You’re not an Esquire model.
2.  Whoever invented Photoshop is a genius.
3.  Who cares?  You should look like you, not a cover model–unless you’re a cover model.

Author unknown

Traditionally it’s not recommended to wear a button down shirt with a tie, but in the last years I see that often. Is it ok and if yes, what are the prerequisites to do so?

- Ben

Whoever told you you shouldn’t wear a tie with a button down shirt should go crawl under a rock.  It’s totally acceptable and in fact I encourage it.  Instead of thinking in prerequisites think of proportions.  Button downs of today from shirt makers like GANT come with shorter collars and less roll than those of yesteryear from Brooks Brothers.  While they can be worn with a tie, button down collars are inherently casual so keep the tie casual too.  Try a silk knit, wool plaid, or cotton madras.  The shorter the collar the slimmer the tie.

Should guys ever wear a ring if it’s not a wedding ring or championship ring?

- Mike D.

Men should keep jewelry to a minimum overall.  However, for those guys who like to sport a little more bling rings are an option.  Depending on lifestyle and work environment men should limit rings to a wedding band, class ring–from college I hope—or a signet ring displaying a family crest or professional association and/or club.  Unless your name is P. Diddy or you can make another man disappear by making a phone call avoid pinky rings.  I wear my class ring proudly and receive compliments regularly.

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Grant Harris is Owner & Chief Style Consultant at Image Granted; a Washington, DC based Image Consulting Company dedicated to solving the complex image, style & fashion issues of today's professional man. He has a healthy obsession with socks. Follow him on Twitter & Facebook.

  • http://www.xymen.com Patrick Ouzts

    Regarding the man bag issue, I have a Saddle Back Leather satchel. I love it and can carry it almost anywhere – work, vacation, day trips, etc. I would like a more formal briefcase at times, but the satchel covers all my needs.

    Regarding looking like a cover model, it might be worth trying to imitate. First and foremost, get clothes that fit. Get them tailored. Most men buy clothes that are too big to begin with. I weigh 200 pounds, I often wear mediums. Get things that fit right and you will look so much better and feel better.

  • http://abetterhuman.blogspot.com Steven

    The stylists in photoshooots also use wires in collars, hems, and other places to make things look messy or crisp way more than normal. I found some ultra-expensive dress shirts with these wires built into the collar, but I think that’s a little weird.

  • MarcTheEngineer

    Notable exception to the “No Pinky Ring” rule – http://en.wikipedia.org/wiki/Iron_Ring

    For Canadian Engineers

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