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What to Wear on a First Date: Pleats and Sheer Polka Dots

Where did you meet the person you’re with now? Do you remember your FIRST date ever with them? I don’t care if you met in a bar, out with friends, on a tropical vacation, in a coffee shop or online and then you tell people you met in a coffee shop; first date jitters can happen to anyone at any age.

Knowing what to wear on a date is half the battle. Why? Because if you feel good and comfortable in what you’re wearing, it can only make the night go as smooth as the butter you’ll be spreading on your dinner roll whether you hit it off or decide they’re just not right for you.

Here are a few outfit suggestions for date night (ladies first):

1. Flirty and fun. Wearing something relatively short? Apply the age old rule of covering your cleavage.

My top &skirt(actually shorts)-H&M, Black Patent clutch- TJ Maxx, heels- Jessica Simpson

2. Blue Suede Shoes: I normally wear 4 or 5 inch heels. On a first date, use discretion. Nothing is worse than falling, slipping, tripping, or being awkwardly tall on a first date.

3. Fall ’11. It’s been the warmest week in months here in San Francisco. I’d definitely wear this on a night out. Pleated skirts are one of my favorite trends right now. Polka dots are back and fun too.

4. For added touch of glamour, if your hair or hair extensions are long enough pull all of your hair to one side. It adds a bit of old Hollywood.

Guys:What to Wear
For a casual dinner, jeans are totally fine as long as they fit well. But if it’s a nice restaurant, dressy slacks and collared shirts are better. I’m liking skinny ties right now too. And always let your date know whether it’s a casual or dressy occasion so she knows what to wear. 😉

5. Most importantly: Be yourself and have fun 🙂

Makeup tip– When I go out and want to make my eyes more dramatic I use Salon Perfect Lashes
If you want a more natural look I prefer #53. They are super affordable and easy to apply 



Avoid a Dating Disaster: (Men & Women) What I mean by this is to watch for signs, clues and sloppiness on a FIRST date so you know that dating this person more than once might be a BAD move.

1. Cell phone mood killers: If your date checks his or her phone more than twice at the dinner table on a date (even if they just need to “check the time”) it’s rude.

2. EX-FILES: On a first date, if someone talks about their ex more than twice and it’s the same ex they are probably either still seeing them, missing them or thinking about them too much for comfort.

3. “Blah, Blah, Blah“: If your date talks NONSTOP about themself, doesn’t ask you questions or doesn’t listen when you answer, CUT it off fast. They probably won’t even notice because they’re so self-consumed.

What do you think? What are your first date deal-breakers?
Have a great weekend!

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  1. Sérgio Pontes says:

    I like your photos, they are very nice

  2. Mol†o ❤ Fashioη says:

    What a beautiful outfit! I love the softness of the color and the texture, and then the contrasting pop of the bright blue shoes.

  3. Thanks for the comment!Cool outfit,I love the blouse!I have a fashionblog also 🙂 Would be so happy,if you could check it out.xx neverdreamedaboutthis.blogspot.com

  4. stylemailbox says:

    such a lovely outfit, you look great!


  5. Beauty and Bows says:

    Beautiful outfit, I love the colourful shoes combined with the neutral clothing.

    Kisses, Melanie
    (Beauty and Bows)

  6. omg dale! awesome tips! haha! love the pleated skirt!


  7. what a coincidence… i just posted a new post earlier today because yesterday was (our) first date anniversary! but i wasn’t dressed this cute on our first date 7 years ago! haha

    love the outfit though. super adorbs! i love the pleats! is it a recent purchase from h&M?? i have got to get one!

    & if you don’t mind me asking, where were these taken? i really love the vines with the brick walls.

    any date deal-breaker for me is… the cell phone. it’s rude to: look at it, answer it, text on it or whatever it is! if you’re on a date, pay attention to your date! text/talk to your friends on your own time or have the courtesy to excuse yourself to the bathroom if it’s important. yah know?

    cins- design3rd

  8. ♥ sugarpuff ♥ says:

    You have perfect look <3
    I love the polka dots and your eye make up 😉

    Warm Love,
    Pinkie Anggia

  9. Lea Laqesha says:

    Love your outfit, you look soo good 🙂

  10. I totally love your outfit! you look so darling, and it’s nice post to us girls and maybe boys too XO

  11. Fashion, Art and other fancies says:

    Excellent tips for those in the “Dating Game” – your blouse is so pretty and I adore the colour of those heels. Enjoy the weekend.

  12. Great tips! And yep, the age-old rule is a must to follow haha Love those blue suede shoes!


    A Single Girl’s Musings

  13. This comment has been removed by the author.

  14. Beautiful !! 🙂 xx

  15. If this is how you dress on your first date, I am sure nobody can stop being mesmerized. You look so classy. ^^

  16. Beautiful I cant believe those are shorts adn the pop of blue on the shoes makes it fun.

  17. Blend of Life says:

    Great blog you have! Take a look at mine, because besides fashionable news i have an amazing Give-Away.

    I’m giving away 10 sets of 6 trendy, limited edition nail polish colours!


  18. The outfit is beautiful and you look great 🙂


  19. Chick Flick Journal says:

    very cute outfit and I’d like the shoes if they were a bit higher

  20. “…half the battle.” what kind of war dates do you go on? 😉

  21. so cute! this is a lovely outfit.

  22. Rainy Days and Lattes says:

    Gosh, you look amazing. Everything from your hair to your outfit! 🙂

  23. Great blog!

    please visit my blog and follow if you like!


  24. Wooow I love this outfit!!!!!!!!! ^.^
    If you want visit my blog http://www.thegiuliasbag.com

  25. SassyUptownChic says:

    Super great advice! I wish I could’ve given this handout to the GUY. LOL I love your outfit. Very romantic and fun. Happy Sunday! 😀
    SassyUptownChic xoxo Kim

  26. What Sadie Did says:

    Great post, especially the tip about the heels! I wrote a funny date-wear article for a magazine a few years ago, it was great fun but also offered similar advice. The best thing you can do is always to be yourself 🙂

    Sadie x

  27. This is such a cool post–I love polka dots, and the suggestions are real and brilliant–no one wants to face plant on a first date =)

  28. What a cute first date outfit…great choice…..


  29. Fátima Payán says:

    u’re really pretty! love your look

  30. First of all, cute outfit! That would def get you a second date! And great idea about comfy shoes.

    Dealbreakers are guys who don’t at least offer to pay the bill (I once had a guy who made me pay…on my birthday…and he was my boyfriend!) Oh, sloppy eating habits and worst of all…boring or no conversation also does a guy in!

  31. Great tips! I very much love the blouse and the shoes are very cute! 😀 I especially love their color:D

  32. Ahaha.. I love the idea of this post! And extremely cute outfit indeed. I just regret my hair are not long enough to put them on one side as you suggest.. quite sexy indeed!


  33. Caradee: Fashion Blogger says:
  34. You look absolutely stunning!


  35. Dallas Shaw says:

    i love a bright blue shoe

  36. This outfit is so romantic! I love the bright color of the shoes! Come back soon to visit my blog, I’ll be waiting for you!!

    Cosa mi metto???

  37. Angela [Simply Simple Me] says:

    So true: checking your phone is a buzz kill. Wear a watch if that is your excuse!

  38. My Favorite Pieces says:

    You look so pretty,love the polka dots.Polka dots are trending for this fall:)Cute outfit and the shoes really give this look a pop.

  39. so cute!! Great look, love your shoes!

  40. audrey marie says:

    this is such a cute outfit – and i love your nail color!

  41. i would totally date you!! you look so chic — id say the perfect first date look!! and you are spot on with all of your suggestions 🙂 great post!! xo


  42. Sandy at Ooh La Frou Frou says:

    Adorable outfit and fabulous first-date tips!! You look so fabulous that first-date guy would think he died and went to heaven! Hope you’re having a wonderful fall! I’ve had to take a little time from blogging since mid-August since I moved not only home but studio too … but I’m BACK with the Season Premiere of the new fall season of the blog today … drop by! Happy Autumn! xo

    Sandy at Ooh La Frou Frou

  43. @Cindy NGO…I totally agree with you about the deal breakers too and I actually took these pics by an old abandoned building in my hometown Ukiah CA
    @Diana Thanks, your comment made laugh
    @Sandy – So great to hear you’re back! 🙂

  44. Fashion Confessions of a Mommy says:

    What an adorable outfit. Love the pop of blue in your heels.
    Thank you so much for visiting my blog.

  45. If I were getting out to date, I’d be sooo guilty of the cellphone rule.

    Love your outfit though. The white pleated skirt is very lovely. I want to feel confident in a white skirt that isn’t see through!


  46. Loved the top!

  47. *Glam Chameleon* says:

    Lovely, moderate and ladylike outfit! There is nothing not to like!:)
    kisses & hugs
    Jelena (glamfabchameleon.blogspot.com)

  48. RAW Fashion Magazine says:

    Aww that’s definitely a cute first date outfit xx

  49. Natalie Leung says:

    what a great post! it’s a great guide 🙂 and you look great!


  50. Fashion-isha says:

    Hi! Thanks so much for your sweet comment and compliment on my blog! I think this is a great idea for a post I love the blouse…both sexy and ladylike! Thanks for the follow 🙂 – I’m following you as well!

  51. Bravoe Runway says:

    I love this outfit, the polka dot sheer blouse and the skirt look great together. The blue cobalt shoes are beautiful as well! Hmmm first date dealbreaker, a guy who is boring and makes me want to cut the evening short before the wine was brought to the table

  52. Those are some great tips…and I really love the outfit you put together. I think the pop of blue is such a nice touch.

  53. Danielle Celeste Couture says:

    I think that is all good advice except i would say wear a skirt below the knee. You look so cute . I am loving the fortuny pleated skirts, too.

    Love from Oregon USA,

    an evening at the symphony

  54. Okay this outfit is fantastic. I absolutely love the polka dots! Love the dating disaster zone. I’ve totally been there once..or a million times 🙂

  55. Great post and such a cute outfit! I recently found your blog and I’m loving it!
    Would love you to check out my blog in London if you have time =)


  56. I like it it’s very sweet and romantic! xo

  57. Great! Thanks for the comment 🙂
    I like your outfit and nails so much!


  58. love your outfit. very girly with a fun twist. you’re beautiful and thanks for visiting my blog.

  59. you’re so gorgeous! i love this outfit!


  60. daleeeee! you look AMAZING. love the blue pumps. xx

  61. Lovin’ the look, hun. The pop of blue is amazing.

    xx Love & Aloha

  62. Great advices and you look stunning!
    The shoes give the right pop of color! 😉


  63. First of all, love your adorable and sweet outfit, you look fabulous! Your advice is spot on, too.

    Thanks for stopping by my blog.

    Have a great day!


  64. Gawgus things... says:

    This is a gorgeous first-date oufit – I remember my first date sooo well 😉 xxx

  65. Marie McGrath (The Joy of Fashion) says:

    Great suggestions for a date night!! And very cute pics!


  66. I´m soooo in love with this entire outfit! I mean, the polka dots? My biggest obsession right now. And that cute little skirt? So lovely! And those shoes…It´s just per-fect!

    xx Ivana
    Style in the City

    Be sure to enter my giveaway to win an amazing scrapbook software 🙂 http://tinyurl.com/mymemoriesgiveaway

  67. I-like-shoes says:

    Wow.. brilliant outfit! I love the details!

  68. What guy could not totally fall for you, looking as gorgeous as this? This is the perfect outfit for the first date! It’s flirty without being slutty in the slightest. And not only that, it’s really fashionable! I am in love with your shorts especially. They’re so pretty and feminine! And I have wanted some electric blue shoes for so long now!


  69. What guy could not totally fall for you, looking as gorgeous as this? This is the perfect outfit for the first date! It’s flirty without being slutty in the slightest. And not only that, it’s really fashionable! I am in love with your shorts especially. They’re so pretty and feminine! And I have wanted some electric blue shoes for so long now!


  70. What guy could not totally fall for you, looking as gorgeous as this? This is the perfect outfit for the first date! It’s flirty without being slutty in the slightest. And not only that, it’s really fashionable! I am in love with your shorts especially. They’re so pretty and feminine! And I have wanted some electric blue shoes for so long now!


  71. this is perfect for first day, girly and a touch of cool!! just love those pop of blue on your feet!

  72. oops i meant first date*

  73. love this outfit love your hair you look so beautiful!!


  74. in love with the outfit!! pretty blouse and great pop of color in the heels! love!! (:


  75. Megan, The Frugalista Diaries says:

    Love this outfit, especially the shoes…

    And so true on dating mood killers!

  76. Ashleigh Nicole says:

    I love this outfit, you look gorgeous!

    xo Ashleigh


  77. Bang and Buck says:

    gorgeous girl!


    Bang & Buck

  78. Restyle Restore Rejoice says:

    Love this outfit! So chic. And I’m crazy about that nail polish color. It looks great!

  79. Karisa Marieee says:

    haha, I love this post!! The dating tips are silly, but so true 🙂

    YOU are gorgeous!!!! This outfit is sooo cute! Love the green polish and bright blue heels <3

    xo Karisa


  80. Dale, you look AMAZING! Love the polka dots and blue suede shoes.

  81. Modayadairhersey says:

    lovely outfit…

    visit my blog:

  82. Pretty Affair says:

    wow, you look so pretty!! love reading your posts so i guess i gotta follow your blog! xo


  1. Skater Blog says:

    Love Affair Pleated Shorts

    […] s boring and makes me want to cut the evening short before the wine was brought […]

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