jjtr Posted September 4, 2014 Share Posted September 4, 2014 I've been on two dates with this girl and we've hit it off pretty well. The second date ended with two kisses. Anyway, for some reason, I'm now most concerned about my attire. We're meeting after her night class this evening to grab a quick drink and catch some of the football game. We haven't seen each other in three weeks because of vacations and we wanted to at least see each other for a bit (as she's busy this weekend). I've dressed casual, but nice on the first few dates. First date was drinks after work on a Friday and I had on nice jeans and a polo. Second date was dinner at a nicer restaurant and I wore nice jeans and a button up. Is it okay to go more casual now? I'm not talking ratty shorts, stained t-shirt or anything, but are nice shorts, a nice, slim fitting t-shirt from Express and flip flops acceptable? Oh, and a nicer-ish hat? Not a ball cap, but one of those conductor-type hats. I'm sure I'm probably super overthinking this, but I thought I'd ask for advice anyway. Link to post Share on other sites
organizedchaos Posted September 4, 2014 Share Posted September 4, 2014 It's a football game, so casual is appropriate. But IMO, men should only wear flip flops to the beach. On a date, to a game??? No. And no hat either. Personally, not the shorts either. Jeans and a nice fitting tshirt and shoes are fine. 1 Link to post Share on other sites
deathandtaxes Posted September 4, 2014 Share Posted September 4, 2014 It's good you're thinking about what you're going to wear. Flops are rather casual, and hot weather gear, so I'm assuming it going to be hot weather? Hats can be very fun!! The question is - does the hat look good on you? Don't trust your gut on this - take a selfie and get input from a good female friend. Link to post Share on other sites
acrosstheuniverse Posted September 4, 2014 Share Posted September 4, 2014 If she's into you it won't matter what you wear, hat or no hat. It's irrelevant. The presence or absence of a hat isn't going to change whether she's instinctively into you and attracted to you. Just dress appropriately to the situation. You wouldn't wear a suit or a smart shirt and tie to the bar to watch a game. You shouldn't show up at an evening romantic candlelit meal in flip flops or a onesie. It's a no brainer surely. A guy dressing ridiculously on a first date might swing the balance of attraction but if she's agreed to meet up with you three times total I think you're past the point where it matters, as long as you continue to present yourself well. 1 Link to post Share on other sites
veggirl Posted September 4, 2014 Share Posted September 4, 2014 It doesn't matter if she's into you. You are way overthinking it. as long as you're dressed situationally appropriate, you're fine. 1 Link to post Share on other sites
Author jjtr Posted September 4, 2014 Author Share Posted September 4, 2014 Thanks for the responses, all. Definitely know I'm overthinking it, which is funny because I didn't think about it much at all the first two dates. Will probably for sure go with some shorts as it's going to be in the mid-90s today. Ooof! Don't want to sweat through heavy jeans Link to post Share on other sites
Gloria25 Posted September 4, 2014 Share Posted September 4, 2014 Nah, for drinks indoors and watching a football game? Forget the hat. If the football was outdoors - especially in the sun, I'd say hat of course. And yes, I do agree with no extremes when it comes to the cap/hat. 1 Link to post Share on other sites
mightycpa Posted September 4, 2014 Share Posted September 4, 2014 Conductor's hat? Like a blue/gray striped choo-choo hat with a bill? I don't know anyone who would look good in that. That said, if this is who she has to look forward to seeing, you might as well go ahead and get it all out there. Shorts, hat, flip-flops and all. To a sports bar. Link to post Share on other sites
FitChick Posted September 4, 2014 Share Posted September 4, 2014 Conductor's hat? Like a blue/gray striped choo-choo hat with a bill? I don't know anyone who would look good in that. There are dress and casual train conductor hats. Who knew? Maybe bring your toy trains on the date, too, for when the conversation lags. Don't wear flip flops. If you must wear sandals get a pedicure first. Link to post Share on other sites
Diezel Posted September 4, 2014 Share Posted September 4, 2014 If you are going to wear sandals or flip flops, you might as well go all out and wear knee-high socks with those. 1 Link to post Share on other sites
d0nnivain Posted September 4, 2014 Share Posted September 4, 2014 In that venue, casual sports fan is just fine. I'm not sure the style you are talking about but I always found it difficult to kiss someone wearing at hat because you have to work around the brim 1 Link to post Share on other sites
preraph Posted September 4, 2014 Share Posted September 4, 2014 (edited) Sounds fine for football, though not sure about the "conductor hat." Some people are hat-averse, so be prepared to take it off and never put it on again around her if it looks like she throws up a little in her mouth after seeing it. Usually if a woman is hat-friendly, they're going to take the opportunity to touch it or try it on. I would just caution that wearing flip-flops in a mob can get you tripped or break one with people stepping on the backs of them, etc. Edited September 4, 2014 by preraph Link to post Share on other sites
todreaminblue Posted September 4, 2014 Share Posted September 4, 2014 i think the only good hats on guys are like those massive hats......like rodeo hats......i love those hats...they are masculine..........guys really need a horse though to wear one..... i like baseball caps ....on baseball guys playing base ball because it looks ok with whole teams wearing them .....but a guy wearing a cap not playing baseball is well like a guy wearing a train conductor hat and not sitting in a train driving it..she may love hats though.. but if you feel comfortable in it ....wear it take it off inside......that is really quite bad manners to keep it on.....shorts are fine....not you touch me i touch you shorts though(short shorts)....and just a plain t shirt......deb Link to post Share on other sites
Tayken Posted September 4, 2014 Share Posted September 4, 2014 but are nice shorts, a nice, slim fitting t-shirt from Express and flip flops acceptable?Nice shorts up to your knees, yes as opposed to your thighs. Better if the T-shirts doesn't have logo or silly writings on it, personally I'll do a v-neck type. No flip flops please...some kind of mocassin, boat shoe-ish summer wear is prefered over flip flops and definitely no running shoes. As for the hat, this is what I wear http://voguemagz.com/wp-content/uploads/2014/07/JUSTIN-TIMBERLAKE-_1754953a.jpg http://ris.fashion.telegraph.co.uk/RichImageService.svc/imagecontent/1/TMG8108321/m/flatcap_1753303a.jpg Oh...and make sure you put on a hint of cologne. She will notice it and comment. One of my FWBs got me one called 'sugar daddy' (which I am not as she earns more than me) Link to post Share on other sites
Author jjtr Posted September 4, 2014 Author Share Posted September 4, 2014 Nice shorts up to your knees, yes as opposed to your thighs. Better if the T-shirts doesn't have logo or silly writings on it, personally I'll do a v-neck type. No flip flops please...some kind of mocassin, boat shoe-ish summer wear is prefered over flip flops and definitely no running shoes. As for the hat, this is what I wear http://voguemagz.com/wp-content/uploads/2014/07/JUSTIN-TIMBERLAKE-_1754953a.jpg http://ris.fashion.telegraph.co.uk/RichImageService.svc/imagecontent/1/TMG8108321/m/flatcap_1753303a.jpg Oh...and make sure you put on a hint of cologne. She will notice it and comment. One of my FWBs got me one called 'sugar daddy' (which I am not as she earns more than me) Yeah, I grew out of the baggy shorts phase many years ago, thankfully. I keep them around the top of the knee now. Same goes for the silly writing/logos on shirts (sans the smallish logo on some polos). Years ago in high school I probably would have worn the old, "Steel Erection Co." Abercrombie and Fitch t-shirt on a date. Link to post Share on other sites
Tayken Posted September 4, 2014 Share Posted September 4, 2014 You can tell a lot about someone by how they dress....treat it like you are going to an interview, even though it's a 3rd date......things can still go wrong if you get too relaxed. What if she takes the flip flop to mean you didn't bother making an effort? I won't take that chance, but then again I don't wear birkenstocks or flip flops and won't exactly be turned on if a woman showed up to a date wearing it Link to post Share on other sites
Diezel Posted September 4, 2014 Share Posted September 4, 2014 I never knew flip flops were this disliked. Perhaps it's a age/location thing. Once you are out of college... you only wear them to the beach. Or once you are married and neither of you care anymore. That's about it. Jean shorts. Those are out the window too. Link to post Share on other sites
Tayken Posted September 4, 2014 Share Posted September 4, 2014 On the flip side...I personally like a well dressed woman who also happens to smell good...I am not talking the hooker look here with chest on display or the hooters look. I prefer the mysterious / conservative look with a nice dress / skirt. Jeans is a no no for me and don't find it attractive on women at all. Yoga pants / the imitation knock off ones are for the gym, not everyday wear Link to post Share on other sites
IfWishesWereHorses Posted September 4, 2014 Share Posted September 4, 2014 I think the flip flops are a location thing! On the coast we where them almost any casual place. Link to post Share on other sites
Tayken Posted September 4, 2014 Share Posted September 4, 2014 we where them almost any casual place. Pardon......? Link to post Share on other sites
d0nnivain Posted September 4, 2014 Share Posted September 4, 2014 Pardon......? In certain places, especially So California, Florida & many other coastal beach towns you are more likely than not to see everyone in flip flops. Actual shoes are more rare so it's not a social faux pas to wear them on a date even after Labor Day. You show up in Midtown Manhattan, Boston, Philly or Chicago wearing flip flops & yes, people will make negative inferences about you. Link to post Share on other sites
Tayken Posted September 5, 2014 Share Posted September 5, 2014 ^ you missed my sense of humour with regards to what you wrote Link to post Share on other sites
d0nnivain Posted September 5, 2014 Share Posted September 5, 2014 ^ you missed my sense of humour with regards to what you wrote I got it but wasn't sure because I never get on line sarcasm. I don't know "wear" my sense of humor went. Link to post Share on other sites
organizedchaos Posted September 5, 2014 Share Posted September 5, 2014 Meh. I live on the west coast and still think a man should only wear flip flops to the beach or pool. But maybe that's just my old school Sinatra ways talking. Link to post Share on other sites
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