Ah, the first date. It holds the promise of something new, something exciting and hopefully, an outstanding ending. Of course, the first date also tends to come with a certain amount of anxiety because you want to impress her in every way possible while also genuinely enjoying yourself. Though marketing studies suggest that today’s men are perhaps more concerned with appearing well-suited than men were in the past, you’ve probably got a lot to consider when planning your date, and worrying over what to wear should be the last thing on your mind.
To help you get a handle on first-date dressing, we’ve outlined a few of the most common first-date situations and what you should wear in each one. Now you’ll never be over- or underdressed again. With the knowledge that you look smokin’ hot in your first-date fashion, you can relax a little and focus on letting your personality shine through.
Dinner date
On a first date, many people stick to the tried-and-true lunch or dinner meeting. The first impression you each create on one another will set the tone for the rest of the date, so it’s vital that you make a good one. Think carefully about the type of eatery you’ll be dining in. If you’ve made a reservation at an uber-chic restaurant, your first-date fashion will likely require a perfectly tailored, slim-fitting suit along with elegant dress shoes. On the other hand, if you show up looking like you’re red-carpet ready when you’re just grabbing a hot dog, it's more than a little inappropriate, and rather than enjoying her meal, she’ll think you’re totally out to lunch.Although this comparison is a bit extreme, it’s true that many guys do overdress on a first date in an effort to impress their new flames. Realistically, you’ll probably be heading to a restaurant that’s a little more upscale than where you would normally go, but not the ritziest joint in town. The best first-date fashion to wear in this case is a pair of dress pants, like these ones from Zanella, that fit you well and conceal any figure flaws you may have.
On top, a dress shirt is timeless and classy, and most importantly, you’ll look refined but not like you tried too hard. One good pick is this white and grey pinstripe shirt from Prada that will look fabulous on all your first dates for years to come. As far as footwear is concerned, trade in your sneakers for some loafers. For an affordable but stylish-looking pair of basic black leather loafers, try Aldo. Do pay special attention to your shoes and give them a shining a day or so in advance because when people are nervous, they tend to look down, so she’ll probably notice if you’re wearing dirty shoes.
Movie theater
Another standard first date destination is the movies. If you’re in the habit of dressing sharply, then put some effort into choosing your outfit, although take care not to go overboard since it’s not like you have to compete with any of the sleekly dressed male characters in the film. On the other hand, guys who tend to favor casual jeans and sneakers should avoid sprucing up too much just to catch a flick. After all, if you wear more tailored clothing when your style is usually more loose and laid-back, you’re setting the standard for how your date will expect you to dress in the future. So unless you’re prepared to get dressed up every time you leave the house, don’t bother.Essentially, aim to dress in a way that makes you feel comfortable and just be yourself when it comes to fashion at the movies. For a killer look that’s both hot and easy to wear, try a pair of dark straight-leg jeans, like these ones from True Religion, and throw on a graphic printed top, like Nudie Jean’s organic cotton Human Rights tee.
Last but not least, pull it all together and avoid freezing in the theater at the same time by sporting a short-cut jacket. This dark gray nylon model from J. Lindeberg will complement the colors in the T-shirt to immediately turn your jeans and T-shirt combo into something more fashion-forward. On your feet, either sneakers or sporty-looking loafers are appropriate with this outfit.
Night spot
A slightly more unconventional choice for a first date is to go clubbing. When you’re headed to one of the city’s trendiest nightclubs, dress semi-casually and add a few funky elements. Going to clubs is all about being seen and having fun, so slip into your trendiest apparel to show off your wild side and make a surprising first impression. For pubs or taverns, forget about piling on edgy accessories and simplify your look by donning a pair of jeans and a nice sweater.To go straight to the front of the line and get VIP treatment when hitting up a hot club, try a combination of jeans, a striped dress shirt and a blazer in a more unusual color or fabric. These dark rinse jeans with a slight boot cut from James Jeans will never go out of style, so you’ll be able to wear them for all sorts of clubbing as well as non-clubbing occasions. Next, add a collared shirt that can be worn with the jeans alone, as you’ll probably want to show off your dance moves and if you start feeling hot and bothered you don’t want it to be because you’re wearing too many layers on a crowded dance floor.
Do wear a structured blazer until things start to heat up with your date and in the club, however. Try Marc by Marc Jacob’s white sateen blazer. It’s made from 100% cotton so it’s still casual enough, but you’ll look incredibly smart in it nevertheless, and you'll stand out from the crowd in the best way possible. White leather shoes are a good choice to complete this swish look.
Picnic
Obviously, you know you shouldn’t wear a three-piece suit for a picnic-style date. However, don’t think that you can wear shorts with sneakers or ripped-up jeans and a baseball cap just because you’re spending time outdoors. When you’re trying to impress a girl, wearing the clothes you would normally wear to hang out with your male friends at a sports bar just won’t cut it. Instead, focus on coordinated pieces that are laid-back but show her that you didn’t just pull on the clothes from your bedroom floor for this occasion.Since picnics imply decent weather, try a khaki pant or even a pair of linen pants, like these ones from Mexx. Pair them with a white and light blue casual collared shirt, rolling your sleeves up to the elbow to dress your look down a little more. Abercrombie and Fitch is a great place to pick up this type of shirt. Finally, brown sandals will complete your relaxed yet elegant ensemble. Try these thong-style leather ones from Banana Republic. They’re easy to slip off when you start rolling about on your picnic blanket... or at least playing footsie.
FYI: Plan your picnic menu a little in advance, otherwise you might end up serving her cheese and bologna sandwiches and she’ll be disappointed that you put all your effort into your appearance. For a really romantic touch that will knock her socks off, pick up some sparkling wine and a few pieces of high-quality chocolate.
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