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First date outfit advice

post #1 of 14
Thread Starter 

I'm looking for some fashion advice for a first date.  Some basic info on both of us:

 

Me - mid-40 male, 6'-3", thin build but also have small love handles.  Dress 50/50 between business casual and shirt/tie at work, so I have some dress shoes and nice button ups along with nice jeans.

 

Her - mid-40 female, nice figure and dresser.  Seems like fashion is very high on her list.

 

First date will be a tad casual.  Nice restaurant with a few drinks.  Lights are a little low in the restaurant and main courses are $20-25 each.  Not high end but better than a family restaurant.  I'm looking to impress but not blow a ton of cash since it's date #1.

 

It's summer and humid in the Northeast, so a jacket would most likely be out of the question.  Still want to impress anyway.

 

I was thinking one of my dress button ups with a nice, dark pair of jeans but I'm not sure what shoes to wear.  I have a standard pair of black dress shoes but would could use a new pair and thought about buying a pair for this outfit.

 

Thoughts?  If it's a tad budget conscious, I'd be willing to get an entirely new outfit.

 

Also, what about accessories?  I have a nice watch but wasn't sure if other things would look good.  

 

Thanks!

post #2 of 14
Quote:
Originally Posted by wtbrift View Post
 

I'm looking for some fashion advice for a first date.  Some basic info on both of us:

 

Me - mid-40 male, 6'-3", thin build but also have small love handles.  Dress 50/50 between business casual and shirt/tie at work, so I have some dress shoes and nice button ups along with nice jeans.

 

Her - mid-40 female, nice figure and dresser.  Seems like fashion is very high on her list.

 

First date will be a tad casual.  Nice restaurant with a few drinks.  Lights are a little low in the restaurant and main courses are $20-25 each.  Not high end but better than a family restaurant.  I'm looking to impress but not blow a ton of cash since it's date #1.

 

It's summer and humid in the Northeast, so a jacket would most likely be out of the question.  Still want to impress anyway.

 

I was thinking one of my dress button ups with a nice, dark pair of jeans but I'm not sure what shoes to wear.  I have a standard pair of black dress shoes but would could use a new pair and thought about buying a pair for this outfit.

 

Thoughts?  If it's a tad budget conscious, I'd be willing to get an entirely new outfit.

 

Also, what about accessories?  I have a nice watch but wasn't sure if other things would look good.  

 

Thanks!

I can't imagine anything would be wrong with the nice jeans/button-up shirt. A jacket would really complement the set but if it's that hot you won't want to get yourself all sweaty. If the date is in the late evening and you're not walking too far you can at least wear a nice blazer when you first meet, no?

 

You may have more luck with better advice if you were to post pictures of proposed outfits for people to comment on.

post #3 of 14

From a general point of view, you can never go wrong with a nice white button-up shirt paired with dark jeans and classic black/brown dress shoes. I would complement the outfit with a leather watch and belt in the same color as your shoes. Obviously the fit will play a huge part in determining how good you look.

 

A sports coat would be nice as well, you can always carry it over your arm if the weather is too warm, and put it on when you reach the restaurant. It'll come in handy if she gets cold too. Points for being a gentleman!

post #4 of 14

From a personal point of view, i would always choose a darker shirt when eating and drinking - some very nice black long sleeved shirts around. Paired with some nice jeans and quality footwear.

post #5 of 14
Quote:
Originally Posted by mrballs View Post

From a general point of view, you can never go wrong with a nice white button-up shirt paired with dark jeans and classic black/brown dress shoes. I would complement the outfit with a leather watch and belt in the same color as your shoes. Obviously the fit will play a huge part in determining how good you look.

A sports coat would be nice as well, you can always carry it over your arm if the weather is too warm, and put it on when you reach the restaurant. It'll come in handy if she gets cold too. Points for being a gentleman!

I agree about having a sport coat. However, I respectfully disagree with pairing jeans with "classic black/brown dress shoes." Go one way or the other.
post #6 of 14
Thread Starter 

I hadn't thought about carrying the jacket in to the restaurant.  Good idea and keeps me in the general area of how I wanted to dress.

 

What color jacket would you guys recommend?  Let's say I go with blue (her fav color) button up and nice darker colored jeans.  I was thinking a dark grey or maybe navy blue but would obviously need to try them on to know for sure.

 

Thanks!

post #7 of 14
You're a middle aged man, taking your date to a nice - maybe not extraordinary, but at least "nice" - restaurant. You want to impress.

Don't wear jeans. Wear real pants.
post #8 of 14

Linen (my preference for the heat) or silk jackets are also an excellent option if you want to spruce up some but don't want to die from heat. 

post #9 of 14
How about seersucker for a lightweight, semi-casual, hot-weather jacket? Not too expensive, either. (I thought silk jackets tended to be warm.)
post #10 of 14
Quote:
Originally Posted by JLibourel View Post

How about seersucker for a lightweight, semi-casual, hot-weather jacket?
Depends. If this first date at the restaurant is for dinner, I'd say "no" to seersucker.

I like seersucker. I own and wear seersucker. But I see it as more of a daytime thing, not an evening thing.
post #11 of 14
Seersucker would look odd in most parts of the Northeast. Weirdness is not a quality to advertise on a first date.

Maroon is generally better than a black shirt.
post #12 of 14

Since you have dress shoes and nice jeans, I think a sport coat and jean combo would be perfect. It's professional, but it's casual enough where you won't feel overdressed. If you want to know a little more about putting them together, here's an article.

post #13 of 14

To me, a first date is a chance to be yourself more than anything else--the point being that you want to demonstrate who you are to confirm whether she's comfortable with that.

 

So, unless you are also in the middle of overhauling your clothing style, I would be more interested in wearing something that I'm already comfortable with, given the circumstances, rather than "impressing". If jeans and a polo is your idea of $20 meal attire, do that.

 

I went out for cheap Thai for dinner tonight, wearing a full linen trousers/captoe oxfords/sport coat rig. I get all kinds of weird looks because I'm in the South where the state uniform is T's and cargo shorts, which all the other patrons are wearing. But I don't care, because I'm dressed in my clothes.

post #14 of 14
Quote:
Originally Posted by aj805 View Post

To me, a first date is a chance to be yourself more than anything else--the point being that you want to demonstrate who you are to confirm whether she's comfortable with that.

That reminds me of a co-worker I had who was mysteriously charismatic around women. I say "mysterious" because he was neither extraordinarily good looking, nor did he have a particularly good physique. There was just a "je ne sais quoi" about him that made women in the office who were cold as ice to rest of us hover and flutter flirtatiously around him. (Amusingly, his wife was an A-1 drip!) Anyway, one day when I was going out on a first date that evening, he counseled me, "They always tell you just be yourself and act naturally. In your case, however, I suggest you be as phony as possible." I still find amusement in that 40-odd years later. He was probably right!
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