The Look: The Second Date (His)

So the first date went well.  She seems like a great girl and you want to take her out again.  Enter the realm of the second date.  Almost as important as the first, but with a ton more upside.  Most of the nervousness is gone, and tonight you’ll have a chance to really get to know her and not about her school/family/job/friends history.  Tonight you get to know what she likes.  Tonight you get to see how she acts.  And if all goes as well as your gut is telling you, then there may be a third date…

So tonight you have a chance to show a little personality in your get-up.  She agreed to go out with you again, so show her what you’re made of:

From top left…

1. Ovadia and Sons Black Watch Tartan Club Jacket:  This jacket has ‘I have enough guts to wear this jacket in a world of blue blazers’ written all over it.  This is one of those jackets you buy for special occasions, and it looks incredible dressed up or down. Tonight we dress it down a bit, so it becomes the statement piece.  Grin required.
2. Red’s Outfitters Campbell Sunglasses:  Early dinner reservations require sun protection.  Everyone wears Ray Bans.  Get what’s good.  And Red’s is good.
3. Ledbury Grey Brook Shirt:  Go with something soft and understated.  The grey is a nice alternative to white or blue, and it will tone down the check in the jacket.  It won’t be such a stark contrast.  Besides, you want her focusing on you.
4. Allen Edmonds Maistee Belt:  Simple, but with some details (in case she checks it out).
5. Naked & Famous Weird Guy Dirty Fade Selvedge Jeans:  Dark jeans are so much dressier than their lighter alternative.  This is a second date.  Even though they are jeans, they will look better than 95% of every other pair of pants at your spot.  Make sure they fit.  Slim, but not tight.
6. Panterella Pin Dot Dress Socks:  In an outfit like this, let the jacket be the statement piece, not your socks.  Go with a pair of navy pin dots that match your jeans.  And when you have to buy socks, buy good socks.
7. Sid Mashburn Double Monks in Dark Holburn Suede:  Let these boats be the wheels of your personality.  They say ‘sure, I have cap toes, but I like to turn it up’.  And they are suede.  It takes a man to wear suede.
8. IWC Schaffhausen for Tiffany Mens 18k Gold Dress Watch:  Maybe it is a family heirloom or maybe it was a gift to yourself after a good year.  Either way, bring out the big guns.  And tell her what time it is.
9. Alexander McQueen Skull Pattern Pocket Square:  Go with the simple fold here.  No need to fluff this one like a corsage.  Fluffy skulls don’t work.



  1. ANH
    10/24/2013 / 5:00 PM

    That blazer is a head-turner- I would not mind walking on the arm of a guy wearing it.

  2. Bill
    10/25/2013 / 11:39 PM

    This ensemble–the black watch jacket paired with black jeans–you just wouldn’t catch me dead in. Maybe it’s that I’m too old, or too straight. Love black watch, but with khakis or charcoal grey worsted wool trousers, cordovan loafers. I think my pairing will turn that second date into a third. And I’d do a blue oxford cloth vs. the grey Ledbury. Again, more traditional, but that’s my opinion.

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