Wearing a Backpack with a Suit (and 8 Other Common Fashion Failures)

I’m going to take a bit of detour off the beaten track for my post today.

The idea for this post was born out of a casual conversation I was having with a friend of mine Kim (@iamkimu).  We were standing in a line up at Tim Hortons and at we both noticed a guy destroying his beautiful suit with an outdoor backpack from Mountain Equipment Co-op. We decided to come up with a list of 9 fashion failures that guys with suits frequently do.

This list is purely an opinion piece and if you want real fashion tips, check out GQ.

1) Wearing a suit and a backpack

This one is simple. You pay $300+ for a nice suit, get it tailored and it looks awesome. Then you ruin the frame of the suit by tossing a heavy backpack on it. Spend $60 and buy yourself a computer bag or nice leather attaché case.

2) White socks and black dress shoes

White socks should never be worn with black dress shoes. Unless your in grade 6 and also have braces and bad acne. That being said, your socks don’t always have to be black. A really good look is to have a sock with an interesting design that complements the shirt or tie.

3) Wearing a Livestrong (or other charity) bracelet with a suit

Okay, so Kim and I debated back and forth on this one but we decided that this one should be added to the list purely because while these bracelets are usually for an awesome cause, they sort of send out mixed messages. It’s like 99% of you is sending out the message that you’re ready to do business. But your wrist wants to party.  We recommend shelving the bracelet for more casual attire. Instead, wear a nice watch to go with your suit.

4) Wearing a suit that doesn’t fit properly (too big or too small)

This is one of my biggest pet peeves in regards to suits. If you’re going to spend the money on a suit, make sure it fits! A suit that’s too big looks like you’re drowning in fabric. A suit that’s too small….well probably sends the message that you haven’t bought a new suit in awhile. Plenty of tailors can alter your suit at a really affordable price. Also, when buying a suit, make sure the shoulders fit. Everything else can be altered.

5) Wearing two different patterns (suit jacket and pants)

Unless you want to look like your grandfather, then I wouldn’t recommend wearing two different patterns of suit jacket and pants. It can look mismatched or just old. The exception to this rule is if you are wearing a solid color pair of pants and a jacket with a pattern.

6) Wearing a sporty rain coat with a suit

Yes, formal looking raincoats can be expensive. But you can pick up a nice black or beige trench coat on the cheap these days. And it looks way, way better! A nice rain coat paired with a suit, really completes the look.

7) Wearing shoes without shining them (suede being the exception)

Kim wanted me to add this one as he keeps a private stash of shoe polish in his office. Scruffy looking shoes send off the amateur message to a potential employer or client. Give your shoes a good shine before heading out the door and you’ll complete the “power” look.

8) Wearing your cell phone on your belt

Okay, unless you work for the CIA and you need your phone at the ready all the time, then ditch the cell phone holster. It looks ridiculous, especially with a suit. Enough said.

9) Wearing a casual belt with a suit

I’m always amazed at how many people do this. They have an awesome suit (maybe a pinstripe) and then they ruin it with their weekend warrior Hollister belt. Make sure to get a good black or brown belt to go with your suit. And then it won’t look like your heading out for your first job interview.

I’ve love to hear your feedback on any men’s fashion tips (business/formal attire) you have. And the best tip will be posted as number 10 on this list with your name.

The winning tip to add as number 10 on the list was posted by “twocentsplus” who says “Short sleeve shirts should never be worn with a suit”. 


  1. great post. don’t wear a short sleeve shirt with a suit…and if you live where it rains get an umbrella…..rain drizzled doesn’t say polished. here’s an overall tip. focus on your outerwear —95% of the time when you run into people it is at a cafe or on the street, what do they remember….your coat, shoes and purse (if you are a woman)….if you are a guy it comes down to your suit (jacket less) or your jacket, shoes and briefcase. white socks are out and polishing your shoes is definitely in. buy 3 good ones and rotate them with shirts and ties….that is where you can change it up. as a woman i’ve never regretted spending on my shoes, jacket and purses they make me look put together and when i run into people i look polished.

    1. Great tips here! Especially the short sleeve comment. I didn’t even think of that. I’m a big fan of sharp looking outerwear to go with my suit as it really is the first thing that people usually see whether it be on the street or at a first meeting.

  2. Bow-ties:
    If you’re going to dress it up to the point where you need a bow-tie, have enough class to go all the way and get a real one and learn to tie it. A true gentleman ties his own tie and leaves the clip on at the dollar store where it belongs. It shows class, sophistication, and that extra attention to detail. You don’t drink 21 year old Macallum out of a styrofoam cup do you? No, you get yourself a great scotch glass. Likewise, get yourself a real bow-tie to top off your classy look.

  3. Ok so I agree with most of what you said except for the backpack with a suit. True I
    Think it looks bad to wear any backpack with a suit, and when I saw about 97%of the British men wearing them on the tube, I was like wtf?? But I soon realized that many of them use this backpack since they are a)commuting and b) they don’t want to show off having a laptop, like in a laptop bag, so it doesn’t get stolen……now they only wear it when they are on their way back and forth to and from work I should say but it’s not entirely bad :)

    1. Thanks for reading the post and for your insightful comments. From a functional perspective, I agree that it’s probably a good idea to not show off having a laptop. :) And for all the commuters out there, I’m sure they have more than just a couple of books to carry around with them. But maybe they could carry two smaller bags? :p

  4. should be a mandatory reading of all men out there
    another thing is a tie, most of amazing looking suits are ruined with the tie either not matching pattern or badly “tied”. if you can’t do it – don’t wear it

    we got in a massive debate with colleagues regarding the socks. in the UK i noticed a lot of guys wearing suits and funky socks. but positively funky. colleagues said its childish and silly. i find it totally opposite – having a courage to brighten up the day of gray suit with orange socks is amazing!

    1. Thanks for reading the post! Ties are an accessory I avoided for the longest time before I figured out how to match them with an appropriate shirt. One thing I love doing now is pairing the tie and shirt with a snappy looking pocket square!

      I am a huge fan of funky design socks with suits. Although sometimes, people take it too far. I think socks with neat designs have a really neat way of completing the look.

    1. Thanks for the comment Wesley! Yeah, number 3 was a little risky to post but I do agree think that it takes the professionalism down a notch.

  5. I love this, I work with enginners who have to travel with me and they violate these rules all the time. It is downright embaraasing.

    1. I hear you! Kim and I came up with this post because of our frustration with guys totally making fashion faux pas without any good reason for it. It just takes a little common sense and attention to detail! Thanks for reblogging.

    2. What is embarrassing is not know how to spell engineers. There’s such a thing call practicality and I’m sure the “enginners” could teach you a thing or two about that

    1. Thanks for reblogging this post. Sales guys for sure need to take the extra step to make a great first impression!

  6. Matt, my friend, come visit us here in Austin, TX. Suits are virtually a thing of the past and it’s all about being casual. You can dress up for the weekends but there’s not a restaurant in town where you can’t wear jeans. I still enjoyed the post…

    1. Hey Paul, thanks for your comment! I actually disagree that suits are a thing of the past. Maybe it’s a regional trend but in Vancouver and in other places I’ve visited around Canada, suits are really making a comeback. Companies like Indochino and other bespoke custom tailors are booming because millenials are bringing back the formal business attire.

  7. Great stuff Matt. The one that drives me crazy is the suit that doesn’t fit. I’m amazed that people can’t/won’t recognize how much that one little detail makes them look like they’re incompetent.

    When I was a teenager, I worked in a clothing store and you could always tell the guys who came in looking for the “funeral” suit. They were obviously not the kinds of guys who ever wore suits and when they did, it looked ridiculous b/c it never fit properly. They’d have been much better off to go to the funeral in jeans and a t-shirt. Then, at least they wouldn’t have looked like posers.

    Also, I’ve heard it said (and I believe it) that having one tailored suit is better than having 10 non tailored ones. This is why.

      1. It’s worth giving a moment to consider that shoes and backpacks may be a sign that the person is contending with lower back pain. As a business vp whose had it back problems myself for many years, I opt for a satchel with hide away shoulder straps. dpending on the impression i need to make, when i get to my meeting it gets carried (albeit somewhat painfully) by its handle, with straps stowed.

  8. I love this post! I am in the process of teaching my 18 y/o brother how to dress! I would say that the short sleeve thing is totally my number one! And wearing several different bold patterns or ties that are ridiculously too large for the man wearing them. Big ties are decades ago.

  9. I have to disagree about the short sleeved shirt. First of all, if you’re wearing a suit unless someone can see through it or you remove the jacket they have no way of telling how long your sleeves are. I work in a classroom with only two temperatures – too hot and too cold – and I wear a short sleeved shirt to help deal with the heat. I have medical reasons for doing so. I appreciate that in general this wouldn’t apply and if I was going out in a suit I would normally wear a long sleeved shirt, but I felt the generalisation needed pointed out – some people need to wear short sleeves, health is more important than appearance, and for those times it isn’t you’ll still have your jacket on!

  10. I absolutely hate when I see your beautiful suit, beautiful shoes, and the man that has spent a lot of money having a tailored to wearing a college boy backpack over it. so stupid looking. It’s like seeing a woman wearing a beautiful ball room down and dancing with sneakers.

Leave a Reply to mattchong Cancel reply