First Date Fashion

A little nervous about making a great first impression? Worry no more. I’ve got you covered on the perfect outfits for that first date.

Whether you’re a man or woman, the prospect of a first date can often be high pressure. With so many thoughts going through your head, the last thing you should have to worry about is how you look. Your good friend Tee is here with advice on what to wear for a first date, from fine dining to bowling and everything in between.

Dinner at a 5 Star Restaurant

Ladies:  The LBD never goes out of style, so you can’t go wrong in that regard. Make sure to stay on trend by adding a pop of color, whether you add a colorful pair of shoes or a handbag in a bright, juicy hue. Keep jewelry simple; think diamond or pearl studs and chandelier earrings. Although the statement necklace is hot this season, I would avoid it for this occasion. Elegant simplicity is always best at a fine dining restaurant. You don’t want the clanging of your jewelry to overpower your conversation!



Men: Dressing for this sort of date will usually be easier for you. Jackets, and occasionally ties are a requirement at most high-end restaurants. Given the warm weather we’ve had lately, I suggest jackets and slacks in light materials such as silk, wool crepe, linen and cotton. Whether or not you wear a full suit or choose to do separates is up to you. Being that this is spring going into summer, there are numerous colors you can choose from, but depending on how traditional the restaurant is you may want to stick to darker colors for your suits, slacks, and sport coats. A crisp button down or polo shirt is always in order and unless otherwise specified, you can go with or without a tie. Dress shoes and loafers will do nicely, whether you chose to wear a full suit, or mix it up. Jewelry should be kept to a minimum; I would limit it to a watch, at most.




Bowling Alley Date

Probably one of the most casual of all first dates, this one is probably the easiest to dress for. The only wild card will be if you’re going to your local bowling alley versus hitting up a spot like Lucky Strike. (See Dinner and a Movie for Lucky Strike tips)

Ladies: Cute graphic t-shirts, tank tops, jeans, and shorts are all okay for this date. Don’t pay TOO much attention to your shoes since you’ll be wearing those AWESOME bowling alley shows, but bring a pair that’s easy to slip into after bowling. Honestly, there’s not a whole lot you can’t wear to the bowling alley, but I’d avoid too short shorts, tube tops, and heels for obvious reasons.


Men: Like with the ladies, feel free to pull out graphic tees, shorts and jeans. Sneakers are a good shoe choice, but, as with the ladies, don’t focus too much on the shoe, since you’ll be wearing bowling shoes for the majority of the night. You can also throw on a hat, if that’s your style.


Picnic Lunch

Dress for this type of date calls for casual wear, whether it’s bohemian, preppy, or sporty. The key is to wear light fabrics so you don’t look sweaty if it gets too warm outside.

Ladies: You’ll be sitting on the ground, so you don’t want something too short or too tight. Shorts, sundresses, maxi dresses, floral, gingham, seersucker, wedge sandals, flats; it’s all up to you and your style personality. If you’re a hat person, a straw fedora or floppy sun hat will help to complete the look. Jewelry, in this case, is also up to you. My handbag pick for an outdoor adventure would be a large tote; you’ll have somewhere to stash your jacket or cardigan if it gets chilly.



Men: Polo shirts, linen pants, and anything seersucker, or cotton. You’re going to be outside, so you don’t want to wear anything too heavy. Throw on a pair of aviator sunglasses to complete the look.




Dinner and a Movie

The dinner and a movie date is more casual for both men and women, but not as casual as the bowling date. The key is finding the balance because if this date goes well, it can turn into a drink or two at a bar, so you want an outfit that is appropriate in several settings.

Ladies: I’m going to put a little bit of a spin on “What to Wear” for this one. For this particular date, you can basically wear whatever you want (a dress, jeans, heels, flats, a cute top) but the key thing you’ll want to wear is a memorable FRAGRANCE. You’ll be sitting next to him in the movie theater, not talking, but you still want him to be thinking about you. Fresh and fruity or sweet and floral are the way to go. You won’t overpower him, but he’ll remember how you smelled when he goes home that night.


Men: Whether you choose jeans with a dress shirt, or button down, a V-Neck T-Shirt and a Blazer or a cashmere hoodie, you can’t go wrong. Plus, if all goes well, you’ll be able to lend her your jacket if she gets cold during the movie (You’ll get major points for that!)



A final word of advice to the ladies: The great Edith Head once said, “Your dress should be tight enough to show that you’re a woman, but loose enough to show that you’re a lady.” The last thing you want to do is go out there in your freakum dress and get em girl heels on the very first date. You have GOT to leave something to the imagination and give him a reason to call you for a second date.

A final word of advice for the guys: Ladies will look at your shoes and your nails, not necessarily in that order. Make sure your nails are clean, neat and trimmed, and be sure that your shoes are nice because women gauge your attention to detail based on these qualifiers. You never get a second chance to make a first impression.

I hope this has helped you with your fashion choices, but of all the fashion advice I have given today, this next piece of advice is the most important. When choosing what to wear on a first date there is really only one rule: Be yourself. No matter what you’re wearing, remember to be confident and genuine. Those are the most fashionable accessories you can wear and they never go out of style.


Posted on February 18, 2013, in Fashion and tagged , , , . Bookmark the permalink. Leave a comment.

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