Shoes, Socks, and Belt
Subtleties make or break any outfit – so do not neglect putting thought into your shoes, socks, and belts. I, personally, am a shoe fanatic – I love nice shoes! What I suggest for you is to go get yourself some shoes that match-up style-wise with whatever clothes you have picked out. You typically need different shoes for casual versus formal outfits. Shoes can easily set you back a lot of money – so shop according to your budget. Your best bet is to purchase the shoes at the same time you are purchasing your outfits so that you can have the shoe salesperson make specific recommendations. If you cannot buy the shoes at the same time, then be sure to wear one of your outfits when you do subsequently go shoe shopping so you get something that matches. I personally prefer to stay with the basic shoe colors of black and brown … and I prefer the more understated style of shoe (versus something bling), but that is up to you.
Your belt should match your shoes in terms of color. A cheap-looking belt, or a belt that clashes with the rest of your ensemble will kill an outfit fast – so do not neglect the belt. Again, your best bet is to buy the belts at the same time you are buying everything else … so that you can get the input of your female friend or female salesperson.
Socks are also a subtlety to be careful with. Whatever you do, do not wear white athletic socks with any of your outfits – because that tells the world that you are a complete fashion boob. I honestly do not know what the true guiding principles of sock selection are – but I can tell you that I usually pick out socks that match up extremely close to the color of the pants I will be wearing. And you’ve got to have the pants you will be wearing with you in order to pick out the right color socks (unless we are talking about black or dark navy blue, of course).
I, personally, am a minimalist when it comes to jewelry – but I’ve seen many different approaches to it. One of my friends just loves oversize bling rings – he has a wedding ring that looks like something a pimp would wear. Other friends of mine have an expensive watch, but wear no other jewelry. Sometimes I’ve seen large gold chains on men. Whatever you wear, it is largely personal style that guides you. My suggestion is that you be careful about anything bling – as too much bling tends to swing … swing an opinion or judgment instantly either for or against you. As a midlife bachelor, if your goal is to get out there and date, then you probably want to strive for a more neutral opinion from the majority of the world when it comes to jewelry. Just be careful, and give careful thought toward the jewelry you wear. It is always safer to wear less than more! You are far better off spending your money on the rest of your ensemble than on a bunch of expensive jewelry. But hey – if you happen to have money to burn, then at least go buy yourself a really nice watch!
After reading this section on Dress for Success, you are probably saying to yourself – “Holy smoke – all of this shopping for clothes and shoes is gonna cost me a fortune”, and you are 100% correct. But in most cases, it is an investment in yourself that you need to make in order to be able to put your best face forward. It’s all about equipment here – you have to be properly equipped to successfully date … and once you’ve got your new threads, you will feel better about yourself and how you look … which will lead to greater self-confidence, and hopefully an easier time landing a date with the woman you want. Let’s face it, you might be a midlife bachelor because either you or your ex decided “out with the old, and in with the new”. The same philosophy should guide you with respect to your clothes – get rid of yesterday’s news, and stock up on what’s right for the new you. You’ll be better prepared for any type of dating situation – and will have one less thing to be concerned about. Successful dating at midlife is all about removing your personal barriers one-by-one, and then proceeding to get what you want out of life – one step at a time.