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Recently I’ve been paying attention to what kind of shoes my dates have been wearing. It maybe a small detail, but I really think it has a big impact on their personality & if you’ll get along down the road. I take an hour or more getting ready for any date. Either it’s a first meeting for a brief coffee or a second longer dinner date. I like to take pride in my appearance. It would be nice if I’m going to take the effort to get ready, that my date does the same. I guess this goes beyond shoes, yet it’s amazing what some people think is appropriate attire for a date. Maybe it could be the fact that I live in Florida and just everything is more slow paced & relaxed down here. Though, that doesn’t give you a license to go out in public in pajama bottoms, hair in rollers & wearing fuzzy slippers in the afternoon. Yes, I have seen that, it was not fiction.

Personally on a date I like to wear heels, maybe because I feel more comfortable dressed up. Or I have so many I need to get some wear out of them! When a guy shows up in shorts, flip flops & a worn out t-shirt, I really don’t take him seriously. I’m looking for a man, not a boy. This attire might be ok if you’re out on the beach getting ready to go on the boat. Not on a first date. Though, if that’s what you consider dressed to impress, I’m scared of what your “relaxed” look is going to consist of. It might be pajama bottoms out grocery shopping at Wal-Mart!

Tennis shoes on a date makes me think you’re ready to go to the gym, or sprint out the door on our date. Now I’m talking about straight up tennis shoes, not the nicer dark leather comfortable Skechers that you could get away with paired with dress paints. Those kinds are ok. With tennis shoes, again you’re going to have to wear shorts because you would look stupid wearing them with jeans. Sorry Seinfeld, just not classy.

Your shoes should match your age range as well. If your 42 years old wearing Vans with thick shoe laces, untied, well maybe you just haven’t matured enough. Dress age appropriate. Be proud of your age and embrace it. I don’t shop at Limited Too or the Junior’s section. I go to the Women’s Department, because I am a woman.  After turning 30; PAC Sun, Abercrombie, Hot Topic and such stores are off limits! After high school it is not appropriate or even attractive to sag your pants below your ass. Then again, I never liked it on anyone period. Not even Justin Beiber. I don’t want to see your underwear on a first date & it definitely won’t get you a second.  It’s amazing how many 40 something’s I have seen sagging their jeans paired with Vans. That’s just a red flag stating if you haven’t grown up by now, you never will.

You will attract certain types of people based on the attire you wear. If you dress like a successful business man, you will probably attract a successful business woman. If you dress like an 18 year old boy, then you’re going to attract immature girls. Unless that’s your goal, which then you have serious issues to deal with far beyond your wardrobe. (Only ok if you are actually 18.)

This brings me to my favorite attire for a man on a first date; business casual. A full on suite is always hot, but may protray you’re too serious. Business casual is the best. A nice button down dress shirt, tailored jeans and nice dress shoes. It says you take pride in your appearance and care enough to look good for your date, but could either dress it up or down. Khaki pants with a polo is nice too, or jeans with a polo depending upon what you are doing for the date.

This is just what I prefer, you may prefer something else. If you’re gothic, then polo’s are not your thing. Just be conscious of what you wear and how it reflects who you are trying to attract. If you’re going to wear a dress with a plunging neckline and cleavage like Twin Peaks along with clear stilettos, be prepared for requests on your hourly rate. If you want guys to treat you like a lady, then dress like one.  It’s really not that difficult, use some common sense & look in the mirror prior to leaving the house. If friends are trying to give you subtle hints, ask them to be direct with you and don’t be offended.  Everyone can use a little self-reflection every now and then.  Dress to impress! It will make you feel better about yourself and help you attract a compatible person.

Tara Richter

Tara Richter is an Internet Dating Coach in Tampa Bay. She is the author of “The Dating Jungle Series” and an Internet TV Show Host.