The Midlife Bachelor Personal Makeover >> Personal Appearance Rev 2.0 – Look the Part: Dress for Success – Fashion Ensemble 101

New Clothes – Formal, Casual, or Somewhere in Between?
The first thing you need to acknowledge as a midlife bachelor is that you need some new clothes!  Many of us guys have become comfortable in the clothes we’ve had for a while – we tend NOT to think about what we wear very much.  This must change – as it most definitely affects the degree of your success in terms of dating. The first thing you need to figure out is what your new “look” should consist of – based on what is right for you. Again, as I’ve said many times on this website – a good female friend can assist you greatly … so don’t be shy about asking for help.  Find out what she thinks would look good on you. You need to think about what you might wear in the evening when you are out for dinner or drinks … and also what you might wear during the daytime when you are out somewhere doing something like shopping or walking around. You might think about different evening scenarios, too – like out for a casual dining experience (pizza or ribs?) versus a formal dining experience at an expensive restaurant. You want to plan to cover all of your bases – otherwise at times you could get stuck with nothing suitable to wear.

What is right for you and your “look” will vary according to who you are, where you live, and what you do for a living. I’ll give you my general guidelines – but remember that yours may be significantly different. Recall that saying I discussed earlier – adapt, not adopt? That is highly appropriate here! For me, I usually default toward over-dressing when going out. Now I wear a shirt and tie with slacks when I’m at work visiting clients – and so many times, I’ll just stay dressed like that if I’m going out in the evening.  On days where I work out of my home office, I’m typically dressed in jeans and a t-shirt – and so on those days, if I’m going out in the evening, I most definitely change into something appropriate for the style of place I’m heading to. If it is a fairly casual place, I typically wear a short sleeve collared shirt with semi’formal khaki pants. If I’m going to a more stuffy and formal restaurant, I probably would wear a long sleeve collared shirt with more expensive slacks. If where I’m headed is super formal, I might even put on a suit – it really depends on what others at the establishment would be wearing. As a general rule – wherever you are going, you don’t want to stick out like a sore thumb in terms of what you are wearing. You don’t wear a suit and tie to a baseball game, nor do you wear a t-shirt and jeans to a wedding. The BEST THING you can do is to take the time necessary to think about where you are going, and what the atmosphere is – and then dress appropriately. In my case, I might even dress just a little more upscale than what is standard … not so that I stick out like a sore thumb, but maybe so I stick out just a little.

Once you have a good idea about how you want to look in various scenarios, it is time to go shopping! Men often hate to shop, so don’t make the mistake of hurrying through making your selections just to get it done and over with. No – quality is the key. And you probably should seek the input of a woman to help you through the process so that you don’t mismatch color combinations, or purchase clothes that look dorky, etc.  Female friends can help, as can good salespeople.  One word of caution regarding female salespeople – your best bet is to use a female salesperson that is near your age. The young twenty-something female salesperson might pick you out clothes with her father in mind. You don’t want to look like her dad – you want to look like a virile midlife bachelor whose clothes say “successful ladies man.”  Most men are not that interested in style, but if you know one who is and seems to like helping people, go for it. If your style is flat-out bad and/or the people in your life are not able to help much, you could always go to a stylist or image consultant.  Just make sure you are not overpaying and that the professional often works with men. Whoever is helping, do not be talked into a style that is not going to make you happy.

In addition to quality, you also need to think about quantity. In other words, get enough outfits so that you are not likely to wear the same thing twice within a three week period.  Nothing turns women off faster than wearing the same outfit too much – and women NOTICE stuff like this!  Be sure you get shirts that can be worn with different color pants, and vice versa. I would say that you should have at least twelve casual outfits, maybe 5 semi-formal outfits, and at least one formal suit. If the twelve casual outfits have shirts that can be worn with two different colors of pants – then you now have 24 different outfits, right? You get the idea – don’t under shop!

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.