What Should You Wear? A Man’s Guide to Looking Your Best


“I want to look better.  What should I wear?” I get that question all the time. My answer, however, might surprise you. I don’t point people towards a store, a brand, or even a personal stylist. Before you buy the latest edition of GQ for fashion advice, consider the following:

a man's guide for dressing well and looking good

You have to “feel” good before you can “look” good. Your outlook and attitude have more impact on the way you look than what you’re wearing. You can dress up in the most expensive designer suit, but if you’re a miserable, unhappy person, you’ll still come across as, well, a miserable and unhappy guy with nice clothes on.

All about the fit. Beyond style, well-fitting clothes will make you look your best. I cannot tell you how much better a man looks wearing clothing that fit, instead of over-sized shirts and ill-fitting pants. I wrote more about it here.  This is more on how to wear it than just what to wear.

Know your body. No matter the current trends, find styles and colors that are best for your body and skin tone. There are some universal rules in fashion that one should not break. If you are carrying extra weight, for example, you should avoid wearing horizontal stripes and solid whites. They make you look even bigger. Black, on the other hand, covers a multitude of sins.

Say “no” to fashion pressure. If you’re not comfortable in it, don’t wear it. If you don’t think you can “pull it off” then walk away from it. There’s nothing more unattractive than a man who’s uncomfortable in his own skin. And if your wife, girlfriend, mother (boy that’s a therapy session line up!) buys you something you just cannot see yourself wearing, be true to  yourself and just say no.

What other suggestion would you offer to help a man figure out what to wear?

  • Great advice!! The only thing I would add is “Listen to your wife”. 🙂

    •  That goes without saying! Specially if you’re wearing a Spider Man outfit, so I hear.

  • CheryL

    Great Article!  Sooo True!  I would encourage a man to introduce himself to a ‘stylist’ … found at every Large Department Store.  Spend 60 minutes with that person.  They can direct you to clothes that ‘Rock’ your body type in a short amount of time!  It’s like having a gps in Boston!  It helps .. it pushes you out of your ‘old’ shopping routine… many times I see people wanting to update their iphone, laptop & mac .. but are soooo afraid to update their wardrobe and wear a ‘new stylish’ shirt because of the ‘price’ … or image; ‘it’s Not me’ …get over it!  Thanks for this article!  Your quote above;
    “You can dress up in the most expensive designer suit, but if you’re a miserable, unhappy person, you’ll still come across as, well, a miserable and unhappy guy with nice clothes on.”  Reminds me of the saying about money … and I am reminded that it still makes misery better!  There is  Great Feeling that comes along with a Great Outfit … for a man or a woman!  Now, please excuse me; I must go shopping now .. I need that Retail Therapy!  (smiLe)

    • Good point CheryL. I find that Nordstrom’s does the stylist thing better than most all other department stores. Your personal stylist will stay with you throughout your entire shopping experience.

  • I agree 100%  The problem with most men is they’re afraid if they become fashion conscious they’ll suddenly find themselves watching Project Runway and saying things like “Fabulous!” (OK, so I watch PR and occasionally jokingly say “Fab”).  Some also see it as being vain and self consumed.  All men should put more thought into their appearance, even if it’s like you said, a well fitting pair of jeans and black t-shirt.

    I also agree that clothes won’t make you a better person. However, if you have a good outlook, dressing well will enhance that.  You’ll actually carry yourself more confidently . (in my humble opinion)

    •  Like judging a book by its cover, we judge a man, or woman, but our first impression. While it’s not a desirable trait, we all do it. It’s just human nature. The better you look, the more opportunities you’ll have. While it might be shallow, it’s true.

  • Douglas Pek

    Great post! Specially the last lines! Once in a while my mother comes up with some pretty interesting choices of ‘fashion’ gifts!

    •  My mother stopped buying clothes for me when I was about 10. Or should I say, I stopped my mother from buying my clothes when I was about 10. 🙂

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