Anatomy of a Date Night Outfit

Long Black DressThe Dress:  

The dress should be something you will find sexy, but something that she will also feel comfortable in.  You should know your lady well enough to know she hates her legs, or whatever other blah blah crap she complains about that you never notice.  If you don’t know or have any questions, simply look in her closet.  This should give you all the information you need.  Is every dress you see long?  Are they all hoochie skirts?  Does she even own a dress?  Depending on the answers to your questions, you should be able to have a good starting point to get shopping.  Your best bet is to pick out a few that you like and if you are having trouble deciding, simply send the links to one of her friends and ask them.  You should get an honest answer out of them.  You don’t have to tell them everything, just tell them you are shopping for her birthday.  Chances are they will either forget about it or it just won’t slip.  Also keep in mind that you want to be appropriate to the venue.  So if you are going to a ball, then a long dress is more appropriate than a short one.  Either length would be appropriate for a casino.





Black Shoes

The Shoes:

The shoes are the second most important part of the outfit.  All things comfort and practical go out the window here.  Chances are, the more they look like medieval torture devices, the “better” they are.  Again, look in the closet, ask a friend, etc.  I cannot really give too much advice on how to match the right shoe to the dress you picked out.  Good luck.  🙂


Black PursesThe Purse:

While seemingly not the most important item in the world, have you ever watched your lady dump her entire hobo duffel onto the bed or kitchen table so she can make sure she has “the necessities” when switching out her purse to match the outfit she has planned?  Trust me, it happens.  While I would love to tell you to get her a nice “clutch” (because you could never carry a purse with a nice dress so it has to be called a clutch) and fill it up with the necessities, you have better luck of winning the lottery than you do of guessing what color lipstick / liner combination she will want to wear with the low light filtering puff pastry powder poofy thing she uses to create a ninja-like smokescreen when she wants to hide something.  Don’t try it.  You will fail.  Just buy the purse and let her worry about fitting the entire Clinique counter in it.



Bra and PantiesThe Good Stuff:

Ok, now for the part you have been waiting for…and will wait all night for.  Here is an area where comfort and practicality don’t necessarily go out the window, but they do have one foot out the door.  For the most part, make this purchase for you, not for her.  And I don’t mean for you to wear!  I mean you should buy something you want to see her in.  Just make sure it works with what other items you bought her.  You will never get to see her in some fancy bra if the straps show in her new dress.  She won’t wear it.  And maybe this is where you can save some money.  Some chicks don’t dig underwear, so why buy it?  Seriously though, go for it.  Goodness only knows when you are going to have the chance to see her in this stuff again.


GlovesOther Accessories:

I know chicks haven’t been wearing gloves since the Titanic went down…or was it the 60’s?  Beats me, it was a long time ago.  But if you think she might like them, go for it.  Retro can be fun.  If gloves are not on the menu, maybe a nice pair of stockings are.  Maybe your lady is a fine pale ale and wants to cover her legs.  Just make sure to keep it classy San Diego.  You don’t want some crazy garter belt straps hanging out of her dress all night long because she couldn’t figure them out.  Save that kind of stuff for later.  That is a whole other kind of post though.




I would not go overboard here if you are dressing her up for a proposal evening, but it is pretty easy to find some fairly inexpensive earrings and necklaces that will really make her feel like she is walking the red carpet.



perfume bottleBonus round:

So if you really want to score some bonus points, you can splurge and buy her some new perfume as well.  This could be a good opportunity for you to buy some new stuff if she wears something you really don’t like.  Or maybe you just want her to wear something as sweet as she is (yeah, I just said that.  You can use it if you want).

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