Tips for Dressing to Impress Cougars: What to Wear and How to Wear It

You know what they say – your clothes reflect who you are as a person. The very first thing a woman notices is your shirt, pants, hair, shoes, and any other accessories you have on. When you’re dating a Cougar, it’s even more important to dress to impress than with younger women. She’ll judge your personality based on how you dress.

Dressing well is all about knowing yourself and what style works best for you. What looks good on one person doesn’t always look good on another. But one thing is certain – dressing well WILL help overcome certain natural physical flaws. Some of the nerdiest guys I’ve ever met look pretty darn attractive with stylish clothes. Clothes can help compensate for a lack of lucky genetics.

Every outfit should include the following…

It doesn’t matter if you’re going for the preppy, businessman, or bad boy look, your outfit should include ALL of the following…

  • Nice looking shirt
  • Well groomed hair
  • Clean shaven face or trimmed beard/goatee
  • Nice shoes that match the outfit
  • Freshly scented cologne
  • Stylish watch, necklace, wristband, etc. (if applicable)

    Dressing to Impress women

    Dressing to Impress women

It’s not all about WHAT you wear…it’s equally about HOW you wear it…

Sure, you can pick out a great outfit. If it’s not worn properly, you’ll look bad. Again, it all depends on the type of person you’re leading her on to believe you are and what looks good on you. I almost always go for the businesslike look. I find that Cougars are almost always attracted to a man that appears to be successful. Businessmen are successful. I wear a loose fitting (but not too loose) button-down shirt and a fancy pair of jeans, along with a pair of dress shoes. Everything I wear fits me perfectly. The outfit is not too snug, nor is it too loose. I look comfortable in it.

Looking comfortable in your outfit is very important. For those of you that want to go for the bad boy look, put on an Affliction shirt (black, preferably) and a pair of jeans. Wear the shirt tight. Of course, if you’re thin, this isn’t going to be a good look. I don’t recommend thin guys to go for the bad boy look. You need to be more muscular. Muscles are associated with bad boys. The preppy look is the best way to go for skinny guys (and overweight guys). Wear the outfit a bit loose-fitting.

The preppy look is the best way to Wear the outfit a bit loose fitting

The preppy look is the best way to Wear the outfit a bit loose fitting