Shoe Style Advice For Men: Shopping With Women and Fashion Tips 101

Never wear sneakers with anything but sports wear (e.g. a track suit). There are exceptions to this rule. Limited edition Nike or some high end Jordans can still be spiffy while not committing a fashion disaster. But even then, you’d probably wear something like a pair of jeans, a hoodie and the sneakers. Choosing a sweater with sneakers is a horrendous nightmare, Please don’t do it! Sneakers can be worn if you know what you’re doing but like I said, It can be best to stick to the classics when you’re wearing sneakers.

Casual everyday shoes send a much different message than the average sneaker kind of shoe that everyone and their brother wears. Make your style smart. I like to be smart wherever I go so I carry a graphing calculator. My favourite makes of shoes not only look smart and stylish but they are also very comfortable.

Step out of your comfort zone and start wearing more daring stuff. It feels uncomfortable at first but trust me it’s worth it. It’s really not that hard to find cool shoes. Just go out and look around. If you have money it’s very easy, if not it takes more work to find affordable nice ones but it’s definitely doable. Take risks sometimes. I used to buy shoes that I felt were “safe”. This usually meant sticking to “safe” colors like black, white, navy blue. Consequently, I ended up having a pretty plain wardrobe. Sometimes you see items on the rack or in a magazine that you could never picture yourself wearing. It’s those pieces that you end up buying and getting compliments on because they’re breaking the rules of fashion.

The shoes, as the rest of your clothing, should be interesting. Look for colors, a mix of patterns or material (say suede + leather) and interesting details. Right now, take a minute or two to study a photo of an interesting pair of shoes and see how many details you can list (even the sole is special!). Now, that’s what makes a piece of clothing interesting. Learning about fashion through the previous exercises might seem tedious, but it’s true that some women will judge you negatively on the basis of your shoes. Take comfort in the fact that at least men’s fashion doesn’t change as fast as women’s.

If fashion holds no interest for you, why not skip the grind of learning about it yourself and instead allow the woman to do the hard lifting for you? Women love to go shopping with men, especially when they first meet them because it’s completely non-threatening. They’ll be at a mall surrounded by people. It’s a similar situation to a woman you just met asking you “Why don’t we hang out tomorrow and watch football?”

This is a great way to both build tension and get the best advice on what to wear. Be sure to pick a woman who has a good fashion sense in what she’s wearing. This works best with shoes. “I need to buy a pair of shoes to go these new jeans I got. Want to tag along with me tomorrow and give me a female opinion?”

I’ve taken several women out shopping for first dates and it’s terrific simply because all the money you spend is on yourself. Plus, if you do want to buy her lunch or dinner it’s perfectly justified and sets a precedent to say: “I don’t normally take women out because I think that’s just an arcane ritual in our society, but since you gave me so much great help I’d love to buy you lunch.” What’s great here too is that you can use this to get some great info. For example, you could enquire: “I’m curious, what was your first impression of me based on what I was wearing?” “What do you think is the ideal look for me?” “Do women find this attractive?” Once you get a woman talking about clothes, she can go on for a long time!

If she says No, don’t let it phase you. Even if she flakes or declines on going shopping, you just got some valuable pointers from her that can help you pick out nice shoes to help you get laid in the future. Congratulations!