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Review my first date outfit for tomorrow night..!

post #1 of 88
9/15/11 at 1:08pm
Thread Starter 
So I have a first date with a fine young lady who works in fashion design tomorrow night.

Here is a rough idea of what I am planning on wearing.

Brooks Brothers Soft Regent Sport Coat (Except mine has dark brown buttons, not white as pictured):

427

Tommy Hilfiger Blue Gingham shirt:

195

Hillside Blue Cross Pocket Square:

200

Dark Blue Denim Jeans + Wolverine 1000 Mile Boots in Rust (both similar to what's pictured except I'm not tucking into the boots):

235

I'm wearing a rust colored belt that matches the boots.

Hamilton X Wind Watch:

525

Billykirk Triple Wrap:

218

I think it all works but I'm not sure if the blue cross pocket square + blue gingham is too much? My only other option is an off white pocket square or none whatsoever.

Let me know your thoughts! If you can't tell, I'm bored at work! Haha
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post #2 of 88
9/15/11 at 2:08pm
I would wear a pocket square with some red in it that doesn't match the shirt. I hope your ensemble fits well. I would lose the watch as well. It is too busy. A sleeker watch with a simple face would suit your look much better.
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post #3 of 88
9/15/11 at 2:14pm
Whats your age and general profession?

Whats her age?

Where are you going?

What time?
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post #4 of 88
9/15/11 at 2:14pm
I am not over-fond of the blazer+jeans look, but I realize many men like it. However, when you match up the jeans with a pair of outdoor boots, the whole effect is sartorially very anomalous--like you're trying to be Wm. F. Buckley, Jr., from the waist up and Paul Bunyan from the waist down.

The blue gingham shirt, blazer and square all seem like an okay combo to me, but I would suggest pairing them with some nice chinos or khakis and a less rugged pair of shoes, maybe penny loafers or something like that.

OR

If you want the rugged, outdoorsman look, keep the boots and jeans and team them up with a plaid wool or cotton flannel shirt and a jean jacket or wool mackinaw depending on how chilly it is where you are.

Just my $.02.
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post #5 of 88
9/15/11 at 2:27pm
clothes look fine; question is how do YOU look?

Btw, I'd wear a leather strapped watch. I know lots of artsy girls who think of those kind of watches as douchey.
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post #6 of 88
9/15/11 at 2:53pm
I regret to tell you that this looks dreadful. It is something from a magazine of twenty years ago and demonstrates no thought about what to wear or how you look. In addition this blazer looks too small for the model in the body and the sleeve length is worse.

Look about you, think and start again.
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post #7 of 88
9/15/11 at 3:06pm
You're on the right track, but there's too much blue. Patrick is right about the pocket square. Keep the fold low key, though. Anything too poofy seems affected in this context.

The boots with this jacket aren't my cup of tea, but I've seen it done and done well. If you can pull it off, by all means.

I disagree profoundly about the jeans and jacket look. Denim provides texture and visual interest. Though there are many exceptions, a date is no place for a suit, while the sport coat provides just enough formality to say he went to the effort to give their date the gravitas it deserves.

EDIT: I am not crazy about that jacket. I get what BB is trying to do there but it comes across like a bar mitzvah get up. Then again, maybe it works on you.
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post #8 of 88
9/15/11 at 5:54pm
Thread Starter 
I'm 26, finance, NYC. She's 23 (ish?), fashion design, NYC.

I agree that I was initially a bit over-ambitious in my footwear selection. It was definitely overwhelming for this outfit. I have just been eager to wear my new boots since I recently bought them. I am also going to opt out of wearing the Billykirk Triple Wrap because it's too much of an additional dynamic for my taste with the gingham pattern, etc.

After throwing a few things on I decided against the Wolverine 1000 miles and subbed in my black Cole Haan Oxford cap toes with a black belt.

I'm pretty set on the outfit... the only thing I am debating is whether to use my Hillside Blue Cross or my "Japan" pocket square which is off-white with a hint of red when folded. Your thoughts?

Japan PS:

331

Blue Cross:

200

Me - Jeans are Gap Selvage:

467

467

467
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post #9 of 88
9/15/11 at 5:58pm
I like the japan one more. Otherwise you are too blue.
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post #10 of 88
9/15/11 at 6:03pm
Quote:
Originally Posted by unbelragazzo View Post

I like the japan one more. Otherwise you are too blue.

+1..
that outfit is do-able. skip the boots....and pls...show more cuff and MUCH LESS watch.
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post #11 of 88
9/15/11 at 6:14pm
Quote:
Originally Posted by GBR View Post

I regret to tell you that this looks dreadful. It is something from a magazine of twenty years ago and demonstrates no thought about what to wear or how you look. In addition this blazer looks too small for the model in the body and the sleeve length is worse.

Look about you, think and start again.

He's going on a date, not marrying Kate Middleton. Get a grip.
You obviously didn't "regret" anything going through your pea of a brain or you wouldn't have been such a dick.

EDIT: Forget it, I read your last dozen posts and it's clear you're a professional asshole.
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post #12 of 88
9/15/11 at 6:55pm
Your clothes are good and you're trim and clean-looking, and your clothes are complimentary to an impression of you as a person who knows how to look good and aware of aesthetic details. Hopefully, you're a kind and decent person and she's a great fun, and your date will be worth the effort. Good luck!
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post #13 of 88
9/15/11 at 7:13pm

Quote:

Originally Posted by Willin View Post

427


imgres.jpeg

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post #14 of 88
9/15/11 at 7:56pm
Change the strap on the X-Wind. A leather strap (aviator straps work with the X-wind) will subdue the presence a little.
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post #15 of 88
9/15/11 at 8:05pm
I think the adjustments you are making will be good. Go with the Japan ps.

First impressions and image aside, how the night goes, that's up to you. Good luck!
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