First Date Fashion Tips: All About Comfort

Dress for the Occasion and Keep Yourself at Ease

Shanny Greer
First Date Fashion Tips: All About Comfort

First impressions last and expectations are high on first dates. You are nervous enough about hitting it off that spending the whole time tugging at ill-fitting, scratchy or complicated clothing is going to compound your anxiety. You want to look respectable and your outfit should be something you could wear to meet his mother. I am not saying dress like a granny but, no need to bust out the twins or flash your booty the first date. Club attire is not appropriate unless you are going to the club and really, if your first date is at a club, you probably aren't too interested in forming a relationship.

Appropriate Attire and Time of Day - No Heels or Stilettos for daytime dates unless you are meeting for brunch or an upscale lunch. If you plan on walking somewhere after lunch/brunch, I suggest flats for keeping your feet comfortable and lessening your chance of injury. The embarrassment of falling off a curb or tripping and planting your face on the sidewalk is not going to put you at ease. Ballgames and picnics, trips to the zoo, anything casual means jeans and a cute t-shirt are okay. Wear an interesting piece of jewelry, especially something you picked up on a vacation, travel stories make for great conversation. Casual does not mean dress like you're going to scrub the floors or paint your den. Casual should be catalog casual, free of stains, holes, wrinkles and for the love of god, not the jeans you bought before you lost twenty pounds. Think as if you are going to have your picture taken by the paparazzi, and you aren't Britney running into Starbuck's sans bra. Distract from your flaws and highlight your attributes! Unless you are jogging, avoid the trainers.

Evening attire depends on the event. You don't need to break out your evening gowns or platinum bracelet unless you're attending a black tie affair. Again, think comfortable and elegant. You want something that he will definitely take notice of but, something that will keep him intrigued. Hugging the curves is good; looking like it took three handmaidens and a tub of Crisco to get you dressed is not. Dresses work for dinner dates, especially wrap-style as they slim the waistline and elongate your silhouette. For concerts, your outfit should match the genre, no cowboy boots at the opera and no gowns at the rock venue. Nice jeans are okay for a show or a movie and don't heavily layer unless its winter, its rough enough avoiding nervous sweat that first meeting.

General Tips

Fabrics- Go with cotton or cotton-blends to fight off overheating and sweating. Being able to move and not fidget makes you look collected and relaxed. You want to be able to pay attention and he wants you to be interested, worrying about what's shifting and bunching is a distraction for both of you.

Size- Keep it like Goldilocks, just right. No baggy shirts or pants with room for Thanksgiving dinner. On the opposite end, don't make yourself look like he paid for your company or that you'll burst at the seams after three bites of dinner. Looking like you made an effort and you deserve a man of substance will impress those worthy of you.

Accessories- Leave the giant handbag at home please. Your purse shouldn't be so large that it needs to sit on the table through dinner or take logistical planning to store it. Take a purse large enough to contain your wallet, your phone, keys and whatever makeup you need to get through the evening. Put some travel size tissue in there as well; in case you are hit with the first date sniffles or he makes you laugh so hard you cry. Bag ladies are not sexy! Riffling through two months of amassed receipts to retrieve something is messy. Men like efficiency and order, show him you have it together. No clunky jewelry. Gypsy earrings, chunky or loose bracelets and Mr. T necklaces will only impede on your comfort.

Makeup- Don't over-do the makeup during the day and even at night. Avoid looking like a showgirl or drag queen. Enhance your natural beauty, play up your eyes don't mask them. Keep the blush looking like you're alive not like you're about to succumb to heat stroke. Try a lip gloss over a cakey matte lipstick; you want to look kissable not like a wet oil painting. Lipstick often unevenly wears off and bleeds out of your lip line. Give yourself some color without appearing as if you just finished four rounds of paintball.

Dressing for that first date is stressful enough. You don't want to be overshadowed by your wardrobe. Impress him with your outer beauty and amaze him with what's inside. Most importantly, keep things simple and make yourself at ease so you can be confident, that's what is most attractive.

Published by Shanny Greer

Has been writing professionally since 1995 for entertainment publications and business content. Currently publishes a blog at contessapantalones.com on topics ranging from relationship to travel advice. Enjo...  View profile

2 Comments

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  • Donna Finkelstein9/21/2009

    From your lips to God's ears!

  • Jesse Greer9/21/2009

    Excellent article! A lot of your general guidelines fit for men, too. Don't dress like you're one of the Gotti's, but like you're going to see your own mother.

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