First Date Fashion Disasters

February 20, 2009 by Anna   | Filed under Ask the Guys


I have been with my fiance now for almost 7 years. Our first date, he wore a short white t-shirt (as if he just took his work shirt off and kept his undershirt on), washed out jeans that were way too big in proportion to his tiny shirt, and bulky black Etnies (FYI: he is not a skater). I fell in love anyways. However, I would like to point out that I will never ever forget his hideous outfit. Thank God he has a personality because his looks alone wasn't going to get him anywhere. Seven years later, I am happy to say that the black Etnies are no longer in the house. Thus, making us a much happier and more stylish couple. I mean, have you guys ever seen a size 13 pair of Etnies? It's pretty ridiculous. It's like 2 black ships on the Pirates of the Caribbean.

Anyhoo, I am addressing this because I felt that even though he was very charming on the date, I didn't consider it an official date because of the way he dressed. I did follow him home from work (no I am not a stalker, at least not on the first date. We worked together.) and we went out to dinner immediately afterwards. Maybe he was nervous and forgot to lay out an outfit, maybe he forgot to do laundry, or maybe he just didn't have a clue. Whatever the case was, I did not let him live it down. And I'm not the only one that has experienced odd fashion choices by guys on the first date. Let's review 3 cases:

bolo tieCase#1: Bolo Tie Man
"After doing some heavy flirting for months with this guy I worked with, he finally asked me out on a date. I was so excited! We planned to go to a dinner and a movie and I spent hours in the bathroom getting ready. Eight o'clock rolls around and I hear a knocking at my door. My heart was pounding and I was nervous and giddy all at the same time. I reach for the doorknob and slowly open the door thinking, "what am I going to say? How big should I be smiling?" Before I could decide on what to do, I opened the door to a bolo tie staring back at me. Confused and extremely curious what the rest of the ensemble could possibly look like, I did a scan from head to toe. A darker small striped button up shirt, the bolo tie, tight black jeans, and cowboy boots. What in the world?! After working with this guy for 3 years, he had no mention that he was a closet cowboy. Turns out he isn't a cowboy at all. He just had no clue on how to dress. I ended up marrying him but not before I took years to perfect his style. But I will never forget the first date because of the outfit."

Dear Mrs. Bolo Tie,

You are a great woman. I don't know how my reaction would be if I had a bolo tie staring back at me. Seriously though, who wears those? It's like a tie/necklace and it needs to be banned. However, I do appreciate his coordination, as his outfit was very themed. Thank goodness you were forward enough and he was open enough to let you redo his style. All I have to say is, it must be love if there was a bolo tie.


anime shirtCase#2: Anime Cartoon Character
"I knew this guy through some friends and we thought lets hang out on a first date. Something with not a lot of pressure so we ended up going to the park and having a picnic. I understand the casual occasion, but what was presented to me was incredibly interesting. He showed up with a horrendous anime shirt (he was about 27 years old at the time) and floral board shorts with coordinating colors. I was speechless and a little repulsed. Because he was a gentlemen on the date, I gave the relationship a go for 2 years and found that an anime shirt also came with Bruce Lee posters and other baggage so it ended. We honestly got into a lot of disagreements and he just wouldn't put away the anime shirts. I knew it was time."

Dear Sailor Moon,

Wow....I did not know what an anime shirt was. I wonder why they make these in adult sizes. I think it's only ok for kids to wear it to sport their favorite cartoons. However, for a 27 year old man...I'm glad you got out. Unless you were an anime fanatic yourself, what would you talk about? You wouldn't be able to hear him over his loud shirt. It's almost forgivable if he didn't try to pair it with floral board shorts. That is amazing. Congratulations, you dodged being Mrs. Sailor Moon.


crazy hair Case#3: Sideshow Bob
"I knew this guy through mutual friends and we had only started talking online. After months and months of talking, we finally decided to have our first date at the museum. Boy was I in for a treat. The fashion, not that bad. He was into vintage almost garage sale clothes and it was not good, but it wasn't horrendous. It was the hair! He showed up at my door with an afro of dirty unwashed hair. I gagged a little. Then I was confused. Did he not know we were going to the museum? This is a perfect way for us to get kicked out! Anyway, I dated him for about a month or two and finally had to end it because he was a huge asshole. I should've known. All of the signs were right there on his head."

Dear 1month Afro Lover,
So you were hypnotized by the hair. It has happened to me before. And funny enough, mine was a complete a-hole too! So, rule of thumb: If your first date is sporting the fro, run for your lives! It is no longer the 70s and I don't think the fro is coming back in style. Put it away. Also, If you have dirty unwashed afro hair, you need an AMAZING personality. Or a haircut before you get off treating people badly. Did the hair stink? Ugh, nothing worse than smelly bad hair or smelly anything for that matter. You were smart to get out soon. I hear your boyfriend now is an absolutely hotty! Congratulations! :-)


So there it is...Guys, let's put some effort into our outfits shall we? You want to dress like you, but a little better. If girls are spending 2 hours in the bathroom getting ready for her date, I say you should put in the same effort. Let the girl know that you want to impress her with how you groom and style yourself. It's hot!


4 Responses to “First Date Fashion Disasters”
  1. Retromusik says:

    Great post! So. Tomorrow I’ll be seeing this guy…I’ll let you know what he wore;)

    Retromusik’s lastest blog post: Saying it all without divulging everything

  2. MizzJ says:

    Wow how did these women even put up with that for even a little while?? I would dump afro man post haste!

    MizzJ’s lastest blog post: Comfy comfy.. uncomfy?

  3. kevin says:

    i am addicted to your blog. keep on doing the great job that’s you’re doing.

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