Hey gents,

So, I was inspired to write this article yesterday morning before meeting K for lunch. I was sitting in Specialty’s, this sandwich / salad / lunch place, the kind of quick eatery ubiquitous in downtown areas filled with corporate offices.

Since it was only 10:30, the space was sparsely occupied by late breakfast eaters, coffee sippers meeting with other coffee sippers, and restaurant staff taking their breaks before the big lunch crowd rolls out of their cubicles and into their eatery.

The restaurant wasn’t super crowded, and apparently I had nothing better to do since I found myself casually observing what my former fellow cube-dwellers were wearing. I noticed many of them making the same mistakes… style basics that the veteran EG reader has probably mastered by now (go YOU!)

I started jotting these things down and realized this would be a great start to the perfect list of things to make sure you’re NOT doing.

Hopefully you find this list helpful, or if you’re a more advanced reader, as an opportunity to review.

(By the way, this article started off with the title “Five Mistakes…”, meant for suit-wearing employees, but then I realized five isn’t a long enough list, and the list itself started to cover things other than suit-related blunders.)

Here we go (in no particular order):

1.) Your suit is too big. The shoulder pads shouldn’t double as fabric-covered awnings for your biceps. Go three sizes down to something that actually fits. Still trying to figure out how your suit jacket should fit? Start educating yourself here.

2.) Wearing a three-button suit? Fasten the middle button. Two button suit? Fasten the top button.

3.) Two-button suits should be your default. Stop buying three-button suits, especially if you’re not at least 6′ tall.

4.) Get a proper pair of dress shoes. Skechers hybrid dress / casual shoes don’t count. Neither do boat shoes or comfort slip-ons. If you’re wearing a suit, wear a classic pair of lace-ups.

5.) At the minimum, own one pair of black leather lace-ups, one pair in brown.

6.) While we’re talking about leather color… Black shoes, black belt. Brown shoes, brown belt. Common sense.

7.) Exact match doesn’t matter, but getting close enough does. Just do your best.

8.) Your socks should match your suit, not your shoes. That is, unless you’re wearing Awesome SocksTM, a.k.a. colorful fun striped or patterned socks… then I hope your pants don’t match those socks.

9.) Stop wearing black suits. Unless you wear a suit every day to work, you probably don’t get many opportunities to wear one. Don’t squander those opportunities by choosing a black suit every time. You’re not an undertaker or a priest. Go with navy or charcoal.

10.) If your jacket, sport coat, or outerwear piece has a vent in the back that’s sewn shut when you buy it, you’re supposed to clip that thread.

11.) Same goes for the tag sewn on the sleeve cuff. Remove it.

12.) Dress shirts are meant to be tucked in. Sport shirts are optional. Know the difference.

13.) Casual Friday at the office doesn’t translate to “Dress Like a Slob”. It also doesn’t mean wear your lawn mowing clothes, and it certainly doesn’t translate to Beach Day, so no flip flops.

14.) In fact, no flip flops ever, unless you’re walking in sand, within walking distance (and heading to) a body of water, or live in a tropical area that more or less dictates what you wear (Miami, Hawaii, Central America, West Africa).

15.) Even if you are in a tropical area, put on some real shoes if you’re not walking in sand or heading to a body of water.

16.) And no socks with sandals, flip flops, anything. That’s a given, right?

17.) Always choose natural fiber over anything synthetic when buying your clothing. Cotton, linen, leather, cashmere, wool… all real fabrics. Rayon, polyester… synthetic.

18.) Buy a steam iron, and use it. Learn how to iron things—especially your shirts—properly.

19.) Stop wearing clothing with huge labels and logos. Save that for the hip hop concert you’re headlining. Oh wait, you’re not a huge music star? Oh, so Louis Vuitton must be sponsoring you, since you’re wearing their logos and giving them free advertising everywhere you go. Wait, what? They’re not sponsoring you? Hmm.

20.) Same goes for Affliction and Ed Hardy tees. You don’t look like a badass biker that kicks ass and takes names. You look like a d-bag, especially with those light wash bootcut jeans and black square toed shoes.

21.) You’re not still wearing bootcut jeans, are you?

22.) Dress your age. If you’re 15, American Eagle and Hollister is fine. If you’re 30, it’s time to upgrade. Not that it’s all about brand names, but there’s an acceptable age threshold for certain brands because of the styles of clothing they carry. If you are 15, you shouldn’t be wearing Gymboree or Osh Kosh B’Gosh. If you’re 30, you shouldn’t be wearing clothing meant for high schoolers. Plain and simple.

23.) To further this point, quit it with the slogan tees and the humorous tees. Wearing it to bed? Fine. Going out in public? Stop.

24.) Dress for the occasion, and that includes your accessories. Sporty sunglasses for when you’re participating in a sport only. All other times, find standard frames that fit your face. Start with something like Ray Ban, who always has classic silhouettes (aff link). Same goes for your watch: Sporty watches like a Casio G-Shock for when you’re being active, something slimmer and classier when in a suit, and a casual watch for your off days.

25.) Pay attention to fit. Your clothing shouldn’t be lung-collapsingly tight or ridiculously loose. There’s a happy middle ground you can (and should) find if you’re an adult male.

26.) Size is different from cut or fit. Just because you know your size, doesn’t mean the cut or fit of the garment is right for your body. Learn your size, then learn the cut that works best for you (regular / traditional fit shirts vs modern / slim fit, regular fit denim vs slim fit denim, etc.)

Phew! This list could probably go on to #1000 and beyond, but I have to stop somewhere. Maybe we can do a part two of this article.

Over to you

Do you follow most of these? Or do you find yourself on the other side of the fence, violating a lot of these suggestions? Would love to hear em in the comments below.


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38 Responses

  1. Morgan Linton on

    Great article and awesome tips, couldn’t agree more about your comment on size vs. cut or fit – spot on.

  2. ChrisReetz on

    One more, and I am guilty of this (until of of course I became a dedicated EG reader) – the thick thread holding the bottom of the sleeve together on that fancy shirt, cut those and insert cuff link.

  3. HoustonWeGotNoProblems on

    Good article, and thanks for building in a tropical climate exception (sort of) to the no-flips rule. I live in Houston where it is mindnumbingly hot in summer. On weekends in Houston, you try to stay inside; if you have to go outside, you wear shorts. Why? Because you don’t want to have to wring out pants when you get home. And with shorts, there aren’t a lot of options shoewise. Boat shoes work fine, but you can get sick of wearing the same thing. So flips are an almost necessary alternative.

    • Barron on

      Yeah, I get that. I have fam in H-town, and I’ve been there during the summer. It’s miserable. I wear shorts when I’m there too. As far as shoes though, flip flops are still my absolute last choice; It looks too college frat boy / bro status. There are plenty of options like boat shoes (which you’ve mentioned), driving shoes, slip-ons like Vans, etc. if you get tired of just wearing boat shoes.

    • grendel on

      No, there’s also canvas shoes like Converse or Tretorn. Basically I don’t want to see your toes. I agree with Barron. Men don’t wear flip flops.

  4. BootcutUp on

    21.) You’re not still wearing bootcut jeans, are you?

    Disagree with this one. Well-fitting bootcut jeans are a necessity. Ever worn straight legs with high shoes/boots? You get the “I’m 12 years old and my jeans are all bunched up” look. Not a good thing. Every man should have 1 pair of bootcut jeans for certain shoes. Now, “baggy”, carpenter, “relaxed fit” jeans….those can go. Straight leg & bootcut are required.

    Other than that, great article.

    • Barron on

      I wear straight legs with boots all the time (like LLBean’s Bean Boots, for example), especially during rainy season / winter. They look great. I wouldn’t want my jeans to drape over my boots anyway. That look is what reminds me of being 12 years old, since all my girl friends had their bootcut jeans hiding their shoes.

      This is all just advice; I personally am against bootcut denim (especially the very flared-out variety) regardless of the type of shoes one wears, but if you sincerely love the look, go for it 🙂

      Thanks for the comment!

      • Dan J. on

        I think it depends on the type of boot. I have a pair of lace up, cap-toe, brogued boots that look great with straight leg jeans. The top of the boot, being lace up, hugs the leg and only comes up to about the bottom of my calf. On the other hand, my harness boots (I ride a motorcycle) are slip on, do not hug the leg and come halfway up my calf. Straight leg jeans barely fit over them and tend to ride back up and stay, leaving with both the bunched-pants-leg and the high-waters look. Not flattering. Boot cut jeans fit and look much better with them.

      • Dan J. on

        I think it depends on the type of boot. I have a pair of lace up, cap-toe, brogued boots that look great with straight leg jeans. The top of the boot, being lace up, hugs the leg and only comes up to about the bottom of my calf. On the other hand, my harness boots (I ride a motorcycle) are slip on, do not hug the leg and come halfway up my calf. Straight leg jeans barely fit over them and tend to ride back up and stay, leaving with both the bunched-pants-leg and the high-waters look. Not flattering. Boot cut jeans fit and look much better with them.

        • Dennis K on

          I have to stick with boot cut because with my size 14 shoes a straight leg has a regular tendency to get caught behind the tongue of the shoe when transitioning between sitting and standing. The larger opening of the boot cut prevents this problem considerably.

  5. Jeannns on

    Good article. I disagree on one point, though; You should take another look at American Eagle – particularly for jeans. It’s not all pre-worn and teenager-y, they have some very good, very expensive looking washes for a fraction of the price. Their fit works well, esp. if you are transitioning in size (weight).
    I have the means to afford more expensive jeans, designer jeans, but I have yet to find a pair as flattering as my AE jeans.

    • Barron on

      As long as the denim there matches the description here: http://www.effortlessgent.com/the-endorsement-the-one-thing-every-man-must-have-in-his-closet/ then I’m okay with it. Thing is, a lot of their styles of shirting, T-shirts, etc, skew young. And I don’t think grown men should wear shirts that “look young”.

      Plus, it’s not about the denim being expensive or designer. Levi’s is a perfect example of a brand that’s around $50 and classic. The 501, 513, 514, 511… all straight-leg silhouettes that don’t break the bank.

      • Don on

        Yes I probably wouldn’t buy things from AE with a logo on it. I do have a buttondown from AE that I took the pockets off so theres no logo and it fits pretty slim.

        I do also agree on the pants, I have 2 pairs of slim chinos from them and it fits great because of they go down to 26/28 which is EXTREMELY rare.

  6. Todd - FM on

    I’ve got a great Navy suit from Zara that fits perfect. I only have 1 black suit which I need to tailor. Anyone have thoughts on if I can where the Navy suit to a “black tie” affair that doesn’t require tuxes??

  7. Daniel on

    5′-8″, 125 lbs. Can’t gain weight for anything. When you said to go “three sizes smaller” I know you weren’t talking to everyone in general, but for me that doesn’t work. At all. I wear a very small 34. And even a “slim” suit is just too big all around (except for the sleeve length.) What would you suggest (given that my budget is wicked small.) ?

    • Barron on

      I was exaggerating when i said “three sizes smaller”, but for you specifically, I’d get a slim fitting 34s suit and get it tailored so the body is taken in. As long as the shoulders fit, you can get the torso more fitted.

  8. Ali Naaseh on

    Fun Fact:
    When I went to West Africa, EVERYONE was wearing suits.
    American men have no excuses when people in one of the world’s most impoverished and climate-unfriendly countries are dressed better than them

  9. jp on

    A very slight bootcut works well with desert boots and a sheepskin coat. No big flares though, I agree. Nothing wrong with three-button suits. Especially if you have a mod-ish look. You can also fasten the top button in addition to the middle button, just not ever the bottom button. Socks don’t need to match anything. I wear bright red socks all the time. But you have to be able to pull it off. But no white socks. EVER. Also, make sure your shoes are more or less clean and shine them a least a little bit. I agree with everything else.

  10. Scott H on

    Great post, but I live in SoCal where Sandals are a part of the lifestyle and the culture. If it’s 110 out and I’m casual, probably sporting sandals and shorts. Men do wear flip-flops, they just wear nice, comfortable, leather ones like Rainbow’s or Reef’s, which go great with a nice straight-fit jean with medium to short break and a sport shirt just as good as some loafers, boat shoes or canvas. Shoes + socks are too hot for my feet. I do find myself wearing shoes more as occasion calls, and definitely more in winter, but in SoCal Summers for casual, non-work occasions? I highly disagree.

  11. Derek on

    Unfortunately, I’ve found American Eagle’s jeans to be outstanding. I agree with most of the rest of their clothing, but they make a great pair of jeans – no skinny bulls*it and no boot cut or relaxed, just regular fitting jeans.

  12. Gazman on

    Agree wholeheartedly with your comment on flip-flops. Those things are awful! Worse: horrible! But I live in Australia and everyone wears flip-flops or as we call them ‘thongs’. A typical man’s outfit: t-shirt, jeans and thongs (winter); t-shirts, board shorts and thongs (summer). When an Aussie man steps out on a hot date, he swaps his everyday tee for a more upscale one, most likely with a massive logo printed on the chest. This is a country wear style and fashion is largely frowned upon. Sad.

  13. Alan on

    It’s a great post, with excellent suggestions. The point on humorous t-shirts: that’s too serious for me. What’s so wrong with funny shirts? You could be verging on dogmatic, no?

  14. Andy on

    One question about black suits, what if one actually was a priest? Seriously, I am shopping for a friend who is a priest and wears black suits and cassocks almost exclusively when out and about. Is black the only color peacoat/overcoat/topcoat that works with black suits?

    • Wallace on

      Ah, I was wondering if I would find a comment like this! I am a deacon, and am trying to find that line between looking “put-together” and looking ostentatious. So far, I think black topcoats are the only ones that look right with blacks. I think it would be possible to pull off a classic pattern (twill, houndstooth) sort of material so long as the colors are black and white/grey, such that it looks dark grey or charcoal from a distance. Still, that strikes me as a little flashy for a cleric. I have been sticking to black (I have a black wool, full length peacoat, looks sharp) and using the scarf for a little bit of color to make it not completely monotone. Peacoats sort of demand scarves anyway. Also, it is HARD to find decently priced black trench coats, and the classic khaki just doesn’t look right to me with the collar. Maybe its just me.

  15. MissEmilie on

    THANK YOU. I’ve been preaching this for years and being stuck in the midwest even in a cosmo city like Chicago — you’d be surprised just how many males just don’t get how to dress themselves.

  16. Chad on

    I’m glad you included Affliction in your list. For some reason people always talk smack on Ed Hardy (deservedly so), but most of the time don’t mention Affliction, which is just as bad! Great list, and keep up the good work.

    • Barron on

      Haha, I simply don’t understand that whole thing. I mean I guess all-over print tees are fine when you’re 20, but I see guys my age or older wearing them. It’s just weird.

      Thanks for reading

  17. Ben on

    There is nothing wrong with boot-cut jeans. In my hometowns, boots are the go-to shoes for work, play, and dress. They also fit better than straight-leg or relaxed-fit. Also, I have a question. None of this applies for a trip to Wal-Mart… right?

  18. Mike on

    I’m 16 and I know all these. its common since. I’m were a tie at least 4-5 days out of seven just cause, well, the girls love it, and it looks good on me.haha