15 {Old Guy} Style Mistakes that Age You INSTANTLY

January 12, 2025
As you mature as a man, your style should also evolve and mature. One of the challenges is that many men don’t know how to do this process seamlessly. What ends up happening is they dress too young, or they look like they’re trying too hard. Another outcome is that they dress too old, which makes them look old.

I want to cover some style mistakes that make you look older than you are and teach you how to fix this situation so you can look stylish and elegant but still mature. Your goal should be to look stylish, but you don’t want to look too young or too old for your age.

Don’t look like your dad!

  1. Geezer eyewear. If you choose incorrectly, you can look like an old man. Stylish men, whether 18 or 85, wear glasses with more structure and substance. You look relevant and more youthful when you wear a cool pair of frames.
  2. Clothing fit. If your clothing is too big and baggy or too skin-tight, you can look old and horrible. Wearing too-tight clothes makes you look like you’re trying to cling to your youth. Also, oversized clothing will make you look dated and sloppy. Collars & Co polos are PERFECT! Use my code ALPHAM for a special limited-time discount on your order!
  3. Pleated pants. Whether you wear corduroys or khakis, pleated pants will make you look older. Opt for flat-front slacks or chinos. They are cleaner.
  4. Dad jeans. Wearing frumpy, boring dad jeans will make you look older. Choose denim that’s a dark wash and straight or slim fit. When I say slim fit, I’m not talking about skinny jeans. Also, oversized jeans will automatically make you look shorter and will not accentuate your butt.
  5. Dad’s sneakers. Dads wear these types of sneakers, making them look old and frumpy. New Balance is not sexy. Also, big, chunky, oversized shoes, whether slip-ons or dress shoes with big soles, will make you look out of touch and out of style.
  6. Too many patterns. Stick with solids, and you won’t have anything to worry about. Young and stylish dudes aren’t matching patterns; they’re wearing monochromatic looks with solid colors. Solid-color clothing that fits you right is classic. It’ll be in style now and five years from now. Combine monochromatic clothes that fit with higher-quality clothes, and you will look stylish longer.
  7. Old clothing. Clothing that looks worn out and beat up is not in style. It will make you look out of date and old.
  8. Over-layering. I’m a massive fan of layering. It adds texture and dimension to an outfit. But there comes a point when it’s too much—anything more than two layers, and you have to be careful. You can end up looking clunky and bulky. Also, wearing too many layers will throw your body proportions off. It’ll make you look heavier, which will make you look older.
  9. Chunky sweaters. Bulky sweaters are the trend for younger guys. But if you’re middle-aged or older, wearing oversized sweaters will make you look a bit old. Look for thinner Merino wool that will drape better on your body and not make you look fat.
  10. Overaccessorizing. Wearing too many accessories will make you look like you’re trying too hard to be young. Choose well-chosen accessories, whether a ring and a bracelet or a necklace and a cuff. Just make sure you’re not overdoing it. Wearing multiple rings, bracelets, watches, earrings, and more will make you look like you’re trying to hold on to your youth. Also, do not use cheap accessories like an Apple watch or Puka shell necklaces.
  11. Bling on suits. Many guys new to style combine a pocket square with cufflinks, a tie bar, lapel flowers, and more. Avoid all that and wear a simple white pocket square with a presidential fold. You sure can wear some subtle cufflinks, but not over the top. But the whole matchy-matchy action, don’t do it.
  12. Leisure or athletic wear. Don’t end up looking like one of the old guys wearing a tracksuit. It’s not stylish. Upgrade to a better option such as Lululemon, Cuts, or other athleisure wear brands that will fit well, are monochromatic, and look more stylish.
  13. Too many colors and patterns. Avoid too many colors and patterns, making you look washed out. If you’re a mature gentleman, stick to monochromatic looks. These will make you look tall, lean, and sexy. Avoid too many Earth tones as well. Too many browns, tans, and greens will make you look like an old fart.
  14. Leather jackets. These are a bit tricky because you need to dial them in, or you look like an old dude trying to look too young. Look for something minimal in construction, such as a leather bomber jacket or a simple zip Moto jacket. Make sure you don’t have too many zippers and padding.
  15. Too dressed up. When you’re going to an event, don’t go overboard. If you’re wearing a suit and everybody else is wearing jeans with casual sweaters, you’ll look a bit out of touch and like you have no clue what to wear.

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