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The first date night. New style or tried and true?

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    The first date night. New style or tried and true?

    Over here, JohnR posted what he was wearing on a date night.

    Now JohnR didn't say if this was a first date or a date of many dates. But it started me thinking...

    When you guys (and ladies if there are any on this thread) go out on a FIRST date, what are you wearing? Do you have a go-to outfit than you trust? Or do you break out something new - maybe even from this site - and give it a whorl?

    I can the see the advantages of both.
    • Tried and true; your comfortable and relaxes
    • Something new - you're exuding confidence about your new look


    Anyway. I am just curious. Cheers.

    #2
    On my last first date (married 9 years in Nov.) I went with an interesting brown short sleeve button down with a blue dashed stripe, dark rinse 501’s and a brown Oxfords. An outfit I’d worn to work before, one I knew worked from a sartorial standpoint, and also one I felt made me look good.
    What you wear isn’t that important. HOW you wear it is everything. Nothing is more flattering than confidence, and being comfortable and confident in what you wear is the best thing you can do.


    Sent from my iPhone using Tapatalk

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      #3
      tried and true, gotta be comfortable to exude 100% confidence. but at this point i've worn just about every combo in my wardrobe.

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        #4
        Thankfully not a problem anymore. I don’t think I could survive in today’s tinder based dating pool. My outfit back then (granted just graduated college) my current self would never wear. Cargo shorts, RL polo and probably boat shoes if I remember right. It was your standard college outfit in the early 2000s. Thankfully my last first date.

        If I went out now a days it would probably be tried and true. Depending on the venue, jeans and a button down. But that also plays into my personality as well. I like to be standard in my dress. Well put together but I don’t strive for new looks just variations of what I like and fits.

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          #5
          havent dated in a long time (married 14 years) but tried and true for sure. I would want to be as comfortable and confident clothing as possible Be you... not a new you that you are testing out. Dont be distracted by new clothing / style.

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            #6
            I've been married for a year (not my first) and we started dating 3 years ago so I can still recall the first few times out. I would have worn something very similar to what I wore this weekend but that's really easy for me to say since I'm a conservative dresser. I don't take many style risks and any new outfit that i have doesn't venture too far off from the rest of my wardrobe. I also agree with the comments suggesting to stick with what you know will work. Not having to think whether your outfit is working, while you should be spending 100% of your energy giving attention to your date, is a sound practice.

            BTW... The reason I dress conservatively is simply because I really don't like to grab attention. I want to present myself as styled and respectable but don't want anyone to "notice" what I'm wearing, necessarily. I do LOVE when I see someone who's extremely stylish or fashionable or whatever. I envy that, in fact. I just don't like attention on myself is all. My wife already knew me somewhat from work when we first dated but I do remember dressing myself and making sure that she would appreciate that I could put myself together nicely, but that I wasn't trying to steal the show.

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              #7
              What a timely thread. I've got my first date post-divorce tonight. I was married for 14 years, now happily divorced (I mean that literally, we're both happy we're divorced and we get along much better now than we did!) and I'm going with tried and true. Higgins Mill (maybe to give me an extra half-inch to inch since, at 5'7", it's needed), dark denim and an OCBD. Nothing too distracting since I'd like the focus to be on my personality. If things develop, I can slowly roll out the obsession with clothes.

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                #8
                Originally posted by MediumTex View Post
                What a timely thread. I've got my first date post-divorce tonight. I was married for 14 years, now happily divorced (I mean that literally, we're both happy we're divorced and we get along much better now than we did!) and I'm going with tried and true. Higgins Mill (maybe to give me an extra half-inch to inch since, at 5'7", it's needed), dark denim and an OCBD. Nothing too distracting since I'd like the focus to be on my personality. If things develop, I can slowly roll out the obsession with clothes.
                I think you're taking the right approach. And, I think that a really great shoe says a lot about a man so let the HM boot do the talking for you

                P.S. Mine was also after a 14 year marriage and also happily. We're better friends now than we were spouses then. Good luck to you!

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                  #9
                  As a post divorce adult, I kept first date to a routine. I wanted to concentrate on presenting myself well and observing my date. A look I liked, a restaurant I haad been to often, etc. That way I am not surprised by crappy food or not knowing where to park etc and I wasnt stressed about if I looked good or not. I actually had my first 4 dates pretty scripted. Standard date with dinner at a known restaurant and usually a museum (absolutely no movies!), extended date (baseball game), activity outing (hiking, record store hunting, shoe shopping), extended chill type day (music festival and a foot tour of one of my favorite hoods or maybe a movie double header). And one of those dates always included my favorite crappy mexican place to be sure it wouldn't scare them off lol. If we made it through those, I would feel more confident in branching out with activities and style. I took the opposite approach out of my divorce...I didnt want to waste time and money trying to get someone to like me and worry about scaring them off so I dove straight into the obsessions lol.

                  Every one of those had an outfit or two that I KNEW I would feel confident in. Occasionally I might get a new shirt for the outfit if I needed a little boost, but not a big variant.

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                    #10
                    Quick update: I had my first date and it went well. Instead of an OCBD, I went with a JCF shirt - mid-blue with tiny numbers on it from last season/year. Looks sort of like a dobby print until you really examine it.

                    The date went well...I'm just old and don't want to put the effort in to woo anyone.

                    Wait, this is a fashion thread. Umm... I also wore mid-calf merino socks, which are total Dappered wheelhouse, so there's that.

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                      #11
                      Do we have an opinion about socks: Sexy or Not? Since we have options; No-Show, Ankle, Crew, Mid-Length, Over the Calf, Hose, and who knows what else. Mathis is of course if the date takes a turn for the better, and at that point you actually care about socks...


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                        #12
                        So true story. Back in my dating days, I had the tried and true go to look. Which for me was jeans and a white button down. I always thought I looked great until I was wearing the same outfit a work one day. My assistant and I were talking about dates (she was dating too) and I referenced what I wore. I'll spare you all the exact details of the conversation, but the downfall on my 'go to look' was ironing. I never ironed my shirt so I looked like a rumpled up candy wrapper on my dates. Lesson learned!
                        Last edited by DocDave; October 23, 2019, 01:22 PM.

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                          #13
                          Originally posted by MediumTex View Post
                          I'm just old and don't want to put the effort in to woo anyone.
                          then don't. don't let other people or general social pressure push you into something you aren't feeling right now. I took 1 year off of women completely after my divorce and only dated very casually for the second year. It took a while for my enthusiasm and patience to come back. By taking the option off the table for a while, I had a lot of stress off of my shoulders. I spent a lot of time with friends, family, and myself.

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                            #14
                            As an old married guy, it's been a while since my dating days. But I vote for tried and true! You gotta be yourself...unless you can be Batman. Then be Batman!

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                              #15
                              Originally posted by tayloreuph View Post
                              Do we have an opinion about socks: Sexy or Not? Since we have options; No-Show, Ankle, Crew, Mid-Length, Over the Calf, Hose, and who knows what else. Mathis is of course if the date takes a turn for the better, and at that point you actually care about socks...


                              Sent from my iPhone using Tapatalk
                              You don't have to worry about it because it is a done deal at that point. Even then, if she has a strong enough opinion about your socks she probably understands how easy they are to change LOL.
                              I can't find the stationary. -- James Bond

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