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First Date Fashion Tips September 26, 2007

Posted by ashleysguide in Dating & Relationships, Fashion.

Standing in front of your closet for hours prior to a first date is nothing new. Changing your outfit seven times and then fiddling with accessories for another twenty minutes should constitute as a first date rite of passage. Count in the time it takes to do your hair and put on your makeup and getting ready can be a marathon-like event. And with all the hoopla, you may be in danger of over-thinking. Simple mistakes can spell disaster for an outfit– and by default the date itself. Here are some tried-and-true tips:

Don’t wear 4-inch heels.
They may make the outfit, but they’re often more trouble than they’re worth. Even if you’re not expecting to do a lot of walking, you should be able to move easily. If dinner goes well, you won’t want to pass up a walk around the park because of your shoes. Even more practical, what if the car breaks down? Being able to walk comfortably can help avoid lots of first-date blunders, so do wear something you can walk in.

Don’t wear jewelry from your ex.
It may be beautiful but it will inevitably come up in conversation– if not on the first date then on the second. Rather than making your new beau feel like they need to compete with the ex, leave the ex out of the picture until the time is right to discuss your pasts. Instead, do wear family heirlooms or funky accessories – they’ll make great conversation pieces and bring up topics that will be more comfortable for both of you.

Don’t gob on the makeup if you don’t usually wear much. While it can been tempting to get all dolled up, it’s better not to go hog-wild. Most likely, your date has seen you before and knows how you usually look – changing your appearance drastically for a date can throw them off. If you do want to wear more makeup than usual, do keep it to a minimum – blush and lip gloss are just fine!

Don’t buy a whole new outfit for a first date. Inevitably, if you bought a new outfit for a date, you probably won’t be wearing that outfit until the day of the date. This makes it hard to know exactly how the outfit will feel or move, even if you tried it on in the store. That new skirt might have looked awesome in the dressing room mirror, but might not feel so awesome sitting in a movie theatre for a few hours. Do take the time to pair up old favorites and clothes that you know will be comfortable for the duration of your date.

Last, but not least, don’t obsess about the way you look. Keep this in mind: they agreed to the date so they must be at least a little interested. Chances are good that they are just as nervous as you. Do focus on the conversation– if this relationship is going to go anywhere, you’ll want to remember what they say over dinner!



1. Emily - September 26, 2007

Classy fashion tips from a classy lady. 🙂

2. Brittany - September 26, 2007

I agree with everything you said. A lot of girls make these mistakes too.

3. Drew - September 26, 2007

Good article! I can definitely see you working for a magazine.

4. becca - September 27, 2007

great article!

5. Erica - September 27, 2007

I completely agree with this article.When you go on the date try not to talk about yourself too much,he/she may think your too self absorbed.

6. Ashley - September 27, 2007

The first date should always be casual, I totally agree. You should never go into it expecting anything, if anything just a good time, but certainly nothing more. First dates don’t always go on to the 2nd date, so it’s best just to play it cool and have fun.

7. leslie - September 27, 2007

nice article, interesting on the jewerly part cuz i got this one necklace i really like to wear and people always mentions it but i dont say its from my ex.

8. Monica - September 27, 2007

Hey Ash, awesome site!

9. Lindsay - September 28, 2007

pretty good tips.it’s best to keep it a little simple.you’re displaying yourself…not your outfit and makeup.

i don’t have a problem with heels on dates.i wear them alot when my boyfriend and i go out.
i do always bring a cute pair of flats with me through…because i have experienced the whole…”let’s go to the park!” deal with him and my stilettos were digging in the grass…lovely.
plus…i wore a new pair out only to have us have to make an emergency stop to buy band-aids for my blisters…haha

it’s mandatory now…as soon as i slip on my heels my boyfriend says “don’t forget to bring another pair of shoes”.

10. Gwen - September 28, 2007

i dress really comfortable when i go on a date,its all about being yourself..

11. Mer - September 28, 2007

Not wearing 4 inch heels is good advice. I read an article in a magazine once about what guys hate. One guy said he hates it when a girl shows up in heels because he doesn’t want to hear her whine all night about how bad her feet hurt.

12. Aliyah - September 28, 2007

I really hate when girls wear twice as much makeup on dates than they would normally. It’s like, you know the dude already likes you when you didn’t have much makeup on or even any at all because he’s on a date with you. There’s no need to look like a clown.

13. Jessica - September 28, 2007

Great post Ashley! I love reading your articles!

14. kayley walker - December 20, 2007

we need somthing for kids

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