Review my first date outfit for tomorrow night..!

Discussion in 'Classic Menswear' started by Willin, Sep 15, 2011.

  1. MikeDT

    MikeDT Senior member

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    We don't know what she does in the 'fashion industry', model, designer, executive?,.. could just be making the coffee for all we know. I was in the 'fashion industry' for 5 years.... employed as a driver. Plus I know a few girls in the 'fashion industry' myself... all sewing jeans in a Guangzhou sweatshop.
     
    Last edited: Sep 16, 2011


  2. JubeiSpiegel

    JubeiSpiegel Senior member

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    +1, well said, let the man be himself but with a bit of refinement :slayer:
     


  3. nytek

    nytek Well-Known Member

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    It's all a bit overwhelming when you first join the forum but you really learn to develop a filter as I get to understand your own style. FWIW, as a 26 year old finance guy myself in the city, the OP looks just fine for a first date and the blazer and pocket square by itself will make him stand out of the crowd.

    People in their 20s wear jeans and polos to go out. Anytime I put on just a simple navy blazer with jeans and suede chukkas, I get compliments of looking dapper, etc. If you wear khakis with penny loafers for a first date (unless you're coming straight for work), you'll come across as a stuffy old man. I don't even want to address the suggestion of wearing a tie as a 26 year old to a first date... wtf, who does that?
     


  4. Joffrey

    Joffrey Senior member

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    Like the look. I think the boots are fine but you can go with something less rugged for a more refined look. Agree with reddish/non-blue pocket square. Don't mind the watch. Good luck!
     


  5. Willin

    Willin Senior member

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    Thanks for the compliments and suggestions, all.

    It's interesting to hear everyone's opinions. I wouldn't consider wearing khakis and penny loafers, etc, on a date. That seems way too stuffy for my taste. I think it's the region I live in but the denim jeans + blazer seems to be a staple look.

    I am taking her to a dimly lit, trendy sushi lounge which plays house music so I'd feel out of place if I had loafers on, etc.

    Regarding the pocket square - I may stick with the "tv" fold. The poof is a little too dandyish for my taste and further calls attention to something that is already demanding attention (white PS with a touch of red). I just don't think I could pull it off.

    I'm not a pilot but I may be using that watch to navigate my way into her pants..! Haha - kidding. Hopefully my jokes improve before this date tonight, ha! Bigger, bolder watches in NYC finance are acceptable. Again I think it's a regional thing.

    To the 26 year old guy in NYC, if you see me walking around in that outfit tonight feel free to poke fun..! Please don't steal the girl off of my arm though- she's a looker.
     


  6. patrickBOOTH

    patrickBOOTH Senior member Dubiously Honored

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    Bolder watches are acceptable, however most true watch aficianados and/or very style (not fashion) conscious well dressed folks prefer subtle watches. I don't think it is regional at all as I am a 26 year old professional in the city also. Bold watches kind of come across to most well-seasoned style guys as trying to hard, or immature. Kind of like when you see a girl wearing a tank top, sweatpants and a Louis Vuitton handbag.
     


  7. Willin

    Willin Senior member

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    I definitely understand the sentiment. I have decently large forearms and hands though so it doesn't feel too overpowering. The X Wind is 44mm which isn't terribly large - it actually seems about average nowadays with most watches around 42mm. I think the silver and gauges just make it have a bit more presence than usual. I'll have to take a picture of the other 10 watches in my collection - it would drive a lot of members here up a wall, haha
     


  8. MikeDT

    MikeDT Senior member

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    What does one do when every girl in the city seems to carry a Louis Vuitton handbag?
     


  9. patrickBOOTH

    patrickBOOTH Senior member Dubiously Honored

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    Tell me about it! My father owns somewhere around 40 Invicta watches :facepalm:
     


  10. Saturdays

    Saturdays Senior member

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    Well just so its clear, he said he's 26, and in finance. I assume he wears a tie to work, that he has money, and that he is treating her to a nice restaurant. Maybe cuffs are a bit dressy, but tie I don't think so.

    I just filled in blanks as I saw fit.
     


  11. althanis

    althanis Senior member

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    He's 26, she's 23. Jeez, pay attention.
     


  12. Bounder

    Bounder Senior member

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    As you are clearly putting a lot of thought into this and you now have the dress bit down, you will need some advice on behavior that is as attractive as your clothes.

    Start here.

    [VIDEO][/VIDEO]
     


  13. Bradden

    Bradden Well-Known Member

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    Not pocket square. The leather strap will understate the watch a little. I think that the 44mm watch with the stainless steel bracelet may be a little bold. The OP mentioned he has a least 10 watches so I am sure he has a few straps to fit with the watch obsession.

    I do not know where you thought that the watch strap would affect the pocket square. That did not come from me. The terseness of your reply leads me to think that you have some pent up frustration. Maybe you should make the switch to decaf. If you felt a little better after your comment, I am glad that I was able to give you an opportunity to let some capital letters fly.

    To the OP I think your outfit works, be comfortable, be confident and be yourself. If that does not work, she does not deserve you.

    Good Luck !
     


  14. VelvetGreen

    VelvetGreen Senior member

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    I suppose you may be correct.
     


  15. ter1413

    ter1413 Senior member

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    same ish!!
     


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