What to wear on second date? - YouLookFab Forum

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What to wear on second date?

annagybe

(website)

Veteran

So I think theme of the date is urban walking. He wants to meet up at noon on Saturday and see where our feet take us.
And yes, this is the infamous anti-art guy. Seattle Art Museum is out because
they closed a bunch of galleries in preparation of an upcoming exhibit.
I'm thinking my black lace-up LD Tuttle ankle boots because they're really comfortable. Or maybe my white golf shoes.
Suggestions? For the record my first date outfit was an oversized cream blouse, Imrpovd woven leather jacket, skinnies and rose gold oxfords.

Dressing

17 replies

Latest reply was from Jonesy

rachylou

Veteran

Hehe. He's gotten you out on a second date, has he? How did he do that? Lol.

Did you by any chance catch the premiere of the new Mindy Kaling (sp?) show on Fox? There's a little vignette in there where she's dressing for a first date and the first outfit is this batwing sequined number - which of course all the girls love and the real man in the office gives the thumbs down to. His advice is something form fitting and simple (like t-shirt and jeans), and shoes you can walk a long way in.

I'm not sure I know what your LD boots look like.

kellygirl

Veteran

Ooh, second date, yay! I'd build around the most comfortable shoes, for sure. I'd aim for something on the sportier side. Can you still wear shorts up there?

annagybe

(website)

Veteran

The high on Saturday is going to be 67, a bit cold for shorts.

kellygirl

Veteran

What about something like your "Fly Girl" WIW? You look approachable and fun (actually, these days you always look that way) but it has some edge, looks kind of urban too. You have the most fantastic wardrobe, I'd have trouble choosing if I were you too!

san

Veteran

Comfortable shoes and good fitting jeans. Let your pretty face and hair be center of attention.

rae

(website)

Veteran

Definitely build around the best walking shoes, whichever those are of the pairs you mentioned. Looks wise, I think your shoe collection can do no wrong, so comfort it is. You wouldn't want to have to turn home because of foot pain if things are going well!

sarah

Veteran

OOH, yes definitely comfortable shoes/boots. Have fun!!!!!!

ETA: Gotta love a man who takes you on a "walking date". I love that. Truly.

Girl X

(website)

Veteran

What's your/his height differential? If you're going to be walking, keeping your heads close together will make it easier to talk - and randomly gaze at each other! And if he's going to be gazing at you anyway, that gorgeous maroon (oxblood?) lipstick couldn't hurt

catgirl

Veteran

Are any of your wedge sneakers appropriate? A gear guy might find them weird, but would be impressed if you out-walk him! I'm excited you are having a second date. Sparks could fly - let's hope they are the right ones!

rachylou

Veteran

I had the same thought, Una, about wedge sneakers for Anna's date, while I was standing in the waffle line.

ironkurtin

Veteran

CLEAVAGE. Show him what he's gonna be missing!

Aziraphale

Veteran

What a awesome kind of date. Hope it's fun! I second the motion for great jeans and comfy but stylish shoes (and I think you've got both those categories covered), and after that, whatever top/jacket combination strikes your fancy that morning.

annagybe

(website)

Veteran

He's significantly taller than me, probably well over 6 ft. Wedge sneakers are out because they're a bit too high for lots of walking.

jayne

Veteran

I think you picked right yourself...but for clothes I think that camel moto you wore for the MaryK challenge is so lovely an brings out/enhances the color or your hair. Wear that!

CocoLion

(website)

Veteran

I concur with the advice to build the outfit around comfortable footwear. I also agree with Rachy's TV guy, go for something more fitted. And maybe stay away from neon except if it's an accessory? Also head-to-toe black, although black and white might work well. The last idea I have is to make sure your eyes look amazing, either through make-up and/or wearing a color that makes them pop.

Jenava

(website)

Veteran

Ooo, yes that burgundy eyeshadow! Other than that I would do another leather jacket, flat shoes that aren't too edgy, casual jeans, maybe a graphic tee?

Jonesy

Veteran

Okay, what is the scoop :)? What are you going to wear? I second (or third) the smoky eye recommendation!!