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What to Wear on a First Date!

Was strolling down the boulevard, doing a little window shopping (was just a tad early for my lunch with the girls—what better way to pass the time?) when I happened to spot the most adorable pair of summer flats in a shop window. Now, I know I was just window shopping, but when you hear your name being called from within, you must follow your bliss, no? Especially when that bliss involves fun footwear and fabulous handbags! Anyhoo, my little stop-over at the boutique took a smidgen longer than anticipated (found a gorgeous pair of retro earrings that are to-die-for!) so I was the last to arrive at the bistro. Which meant, of course, that the girls immediately noticed my newly acquired footwear (of course I was wearing them! They were perfect with my chino capri's and empire wrap top). Well, my dear friend Bailey said that she had been searching far and wide for just such a pair of shoes, as they would be ideal for her date next weekend.

Hold that thought. Date? Bailey? After three seconds of stunned silence we all erupted into squeals of excitement. Dearest Bailey had recently called it quits with her on-again-off-again boyfriend (Loser Boy, couldn't handle the fact that she always beat him at tennis—insecure, egotistical, archaic) and had been a bit "off boys" for the past few months, so this date was a big thing.

"Help!" Bailey implored. "I really like this guy, but it's been so long since I've been on a first date that I can't remember what to do, what to say, and most importantly WHAT TO WEAR!" Which had me flashing back to scenes from one of my fave chic flicks Because I Said So. I love the way Mandy Moore takes a red polka-dot dress and totally spices it up for her first date with a total hottie by pairing it with a black lace cami, chic wide black belt and sassy ballet flats. She then completes the ensemble with a black jacket and a stylish clutch. Oh, and I just adore the full skirted dresses cinched with a wide belt that Diane Keaton wears in the movie! So very feminine, and she totally pulls off the glamorous 50's era Lucille Ball look. Which just goes to show that accessories are a girl's best friend and no outfit is complete without such!

And speaking of Because I Said So, don't forget to ENTER TO WIN a "Mothers in Movies Prize Pack", including DVD copies of Because I Said So, Prime, Something New and Pride and Prejudice.

But I digress. Back to Bailey's dilemma. Our lunch meeting immediately turned into a first date fashion strategy session, which is what we girls excel at by the way, and in no time flat we had worked out the perfect first date ensemble for our darling Bailey, as well as several standby outfits in the case of a last-minute location change.

What to Wear on a First Date

Of course, this totally depends on the date, no? You wouldn't want to wear a girly sundress and strappy sandals to a Warriors game, nor would you appear in designer jeans and a sassy tank for dinner at The Cliff House. First rule of dating attire: Know thy date and whereof he plans to take thee. None of this we'll-figure-out-what-to-do-when-we-get-there stuff. That is soooo high school. Know in advance if it's dinner and a movie or a night at the symphony.

What to Wear to Dinner and a Movie

Dressy-casual as opposed to comfy-casual is the look. A great pair of dressy jeans or wide leg trousers paired with a long tunic layered over a cami. A dainty necklace. Sandals or wedges. A compact little hobo bag for your lipgloss and ID! In warmer weather, a great sundress is also a good choice. Nothing too fancy. Paired with chic sandals or espadrilles and he will be oh-so-glad that he asked you out!

What to Wear to a Rock Concert or Club

You can be a little more bold here, but not over-the-top. A denim, suede or canvas skirt paired with a funky tee or avante-garde top. Check out Romeo and Bella; they have several great tops that would work well here. I particularly love the mermaid tank—very rock star. You could also substitute jeMother's Dayans for the skirt, but keep them dark wash and crisp. Slip into a pair of hot heels, a long necklace, a fun little handbag and an edgy jacket to finish.

What to Wear to a Sporting Event

This is the occasion for comfy-casual (but not sweatsuit-comfy!) Your most sassy pair of jeans. Layer a tank or cami under a tee or girly top. Wear comfortable (but stylish, of course!) shoes since you may be climbing many, many, many stairs. These darling flats are ideal, and they add the perfect amount of pizzazz. Go easy on the jewelry, perhaps just a great pendant on a chain (forego the bangles since they impede clapping and you simply must clap and yell at any sporting event!) and a shoulder bag that can take the heat (i.e. something tough and washable, since it will most likely end up on a floor that is covered with popcorn, soda, ketchup and who-knows-what. A sweater or jacket, depending on the weather, and you are good to go!

What to Wear to a Gallery Opening, Symphony or Elegant Restaurant

A stunning dress. That's a given. Not necessarily the LBD, but I would go with the always-flattering wrap dress in a gorgeous print, or perhaps an empire style. If the neckline feels too bare, layer a flirty cami underneath (this is also a good trick for those with a larger bust, because cleavage is so very distracting!). Subtle jewelry. A really stunning pair of shoes and a unique handbag. One thing to remember: most guys can't tell Manolo from Mossimo so don't worry about designer labels (those are for when you are out with the girls anyway, right?), and don't feel like you need an entirely new wardrobe either. Shop from your own or your girlfriend's closets! Your accessorizing possibilities are endless that way.

Don't Forget:

  • A subtle fragrance. Something that he will remember and associate with you. The key word here is SUBTLE.
  • Clear, fresh skin. Keep your complexion dewy and fresh with RoC Daily Microdermabrasion Cleansing Disks. I swear by these little wonders!
  • Bright eyes. Not as in fluorescent eye shadow, but as in get-rid-of-those-undereye-circles! Here, again, I turn to RoC. Their Retinol Correction Eye Cream is fabulous. Eliminates puffiness and under-eye circles, as well as works on wrinkles around the eyes and (gasp!) crow's feet. Who ever thought up that term, by the way? I much prefer "smile" or "character" lines. Or "expression" lines. Again I digress.
  • Kissable lips. Nothing too garish, nothing too slippery-looking. Think dewy-soft and totally kissable. I love tarte Sunglosses because you get six, count them SIX, gorgeous shades of truly scrumptious lipgloss in one darling quilted denim sunglass case!

Things to Remember:

  • There's never a second chance to make a good first impression!
  • Confident and comfortable. This is not the time to try out new or trendy clothing or hairstyles!
  • Wear the right shoes. Flats or comfortable wedges if you are going to be doing a lot of walking; mid-height heels for dinner and dancing.
  • Wear a bra! One that fits, one that flatters. This is not the place to have the girls flopping about unfettered.
  • Less is more when it comes to style. Not less clothing per se, but don't go overboard on accessories, hairstyles, makeup, perfume. You want to be subtly alluring, not trashy.
Things to Avoid:
  • Flashy jewelry.
  • Itchy or rough fabrics.
  • Heavy makeup or long fingernails.
  • Strong perfumes and sticky hairspray.
  • Clothing that is too sexy or too bare.
  • Anything that is too tight, too baggy or just plain uncomfortable. As mentioned above, confident and comfortable!

All in all, it was a very productive lunch with the girls. And Bailey promises to give us a full report after her hot date. We all know it will go smashingly, since she will be perfectly, confidently, stylishly and comfortably attired!


She She Me

p.s. Be sure to check out the homepage for updates from She She Me. Also, don't miss the great girly merchandise in our Chic Shop and the fabulous finds in the She She Mall!

She She Sponsor:
Barefoot Tess


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