First Dates, For Girls

What To Wear On A First Date? 5 tips For Women

82 Comments 24 July 2009

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by Emma Frisoni

Ever wonder what to wear on a first date?

There I was, standing in my closet, swathed in a silk robe, towel wrapped around my head, champagne glass in hand. I stood wondering, yet again, what to wear on my first date with Jared.

The lucky Dior pumps were a must, but being 140 mm high, lilac and snakeskin, they only coordinated with a few outfits. I was going for the classy, sexy look but it seemed that all the classy outfits I tried on made me look like I was headed to afternoon tea. The sexy outfits I tried on screamed, ‘take me home with you’ – which I wasn’t going after either.
Channeling my inner Carrie Bradshaw, I slipped on the pumps, drew a belt around my robe, and seriously wondered if I could get away with it…

The above scene happens all too often in my world (basically my Saturday night ritual), and although I’ve never actually worn my robe out on a date, that doesn’t mean I haven’t seriously considered it. Confidence is the ultimate accessory, after all.

Luckily, I’ve learned a few things that simplify choosing what to wear on a first date. I don’t have it down to a perfect science yet, but I’m getting there. When my newly single BFF, Lanie, called me this past weekend, anxious about going on her first date in 2 years, I gave her all the tips I could think of. Here are just a few:

One thing to do and four to avoid when choosing what to wear on a first date:

1. Do dress for the occasion

I am a huge fan of getting dressed up. I love it and will use any and all excuses to get glammed up. But if you’re meeting a guy for the first time, you don’t want to make him (and you) uncomfortable by being over (or under) dressed. Don’t wear a sequined dress for a date to Sully’s for burgers and fries (one of my favorite places) or a mini skirt when hitting up L’Espailer.

2. Don’t wear anything too trendy

Although that dress or top may be red carpet worthy in your mind, your new guy isn’t going to recognize the beauty of it. Take my well earned advice on this one – it may seem like a hip, cool outfit, but there’s a good chance he won’t see the cool factor. I have 4 words for you: zebra printed strapless dress (no, not zebra pattern, an actual graphic of a zebra). Let’s just say he wasn’t nearly as impressed as I had anticipated.

3. Don’t wear anything strapless/low cut/spaghetti straps

This one may not seem like a don’t but it actually is. Guys are simple creatures and they have a difficult enough time focusing without your bare skin distracting them. This is an important one especially if you are going out to dinner because he’ll only be looking at your upper half for most of your time. (While you’re seated.) You want to focus on your date and vice versa and bare skin doesn’t help the situation.

4. Don’t go overboard on the makeup

I’ll spare you the details about the time I got a makeover at the MAC counter just before a date. Let’s just say it included me cowering in the wedge behind the John Hancock hastily wiping my face with baby wipes I bribed from a young mom on the steps outside Trinity Church, hoping against hope my date didn’t catch me acting like a homeless person trying to ‘bathe’. Too much makeup scares dudes. If your face looks too perfect, they’re going to be afraid to touch it, never mind kiss you on the cheek at the end of the evening.

5. Don’t wear something you don’t feel comfortable in!

Confidence is owning who you are inside and out. Even if you have the most gorgeous D&G frock for the night, if it doesn’t fit right or it just isn’t ‘you’ then it won’t work. Find pieces that fit well, are comfortable, and speak to who you are and you’ll be a knockout.

There you have it. I hope these tips help you and when in doubt, cinch a belt around your robe and walk around in your heels – anything you put on after that will look fabulous!

Do you have any tips to add on what ladies should wear on a first date or tale of a “wardrobe malfunction” you’ve experienced? Thanks for sharing!


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Photos: carljones,

Hey all! Seth here. I’m thrilled to welcome Emma to The Dating Papers and I hope you’ll give her a warm welcome. If you’d like her to write on something specific or just feel like saying hi, feel free to drop her an email or find her on Twitter. Thanks!


- who has written 8 posts on The Dating Papers.

Hi! I'm Emma. A shoe addict, espresso-drinker, and fashionista. I live and work in Boston, MA, and I am NOT dating Seth. (Figured we'd get that out of the way) You can find me on Twitter as @emmafrisoni =)

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82 Comments so far

  1. Roxanne says:

    I wear nice jeans and a top for a date

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