5 Style Secrets Every Man Should Use to Look Great on a First Date

Let’s be honest: Whether it’s with someone you met on OkCupid or a mystery singleton your best friend’s girlfriend knows, a first date is a necessary evil. Sure, you want to find an amazing partner you can grow old and start a family with; however, until you’ve downed your second drink of the night, you’re probably a bundle of nerves. Does she or he like me? Do I smell okay? Was that dirty joke offensive instead of funny? Do I have broccoli in between my teeth?

In the midst of what seems like a never-ending enumeration of self-directed questions, you also wonder if your prospective beau even likes the outfit you carefully picked out for the occasion. No matter how many first dates you’ve been on, you’ll always be a little anxious until you finally break the ice, but allow us to alleviate some stress. Read on for five style secrets from eligible bachelors and bachelorettes for what to wear on the first date.

1. Nix ill-fitting and crinkled clothes

Pants that are too short

Pants that are too short don’t make the cut. | iStock.com

Just like a job interview or meeting your significant other’s parents (given that the first date was a success), first impressions when meeting a potential partner are crucial. And while some girls or guys won’t criticize your choice to wear a chambray instead of a traditional dress shirt, they are bound to notice when a guy throws on a wrinkled shirt or a pair of ultra baggy pants. Why? In your suitor’s mind, that will translate to you not caring about the encounter.“The way you represent yourself shows that you care and the guy finds you worth making an effort for,” said Catherine Sourbis, a nursing student. “Some men aren’t stylish and that’s fine! But you should always try to present the best version of yourself on a first date.”

Looking presentable is as easy as taking a double take in the mirror and fixing any stains or crinkles before leaving. If you don’t have easy access to a steamer or iron for those pesky button-downs, opt for a lightweight sweater that is more forgiving with wrinkles. As for pants? Use this general rule of thumb: if MC Hammer would’ve worn these in the early 1990s, you shouldn’t. Whether you wear a sophisticated pair of trousers or your best-fitting jeans, choose a pair of pants that is a happy medium between too loose and too tight.

2. Add conversation pieces

a man's watch

One of the best style secrets? Accessorize with a watch. | iStock.com

We’ve all been there before: about 10 minutes into a first date and you’re awkwardly commenting on the bar’s zany décor or memorizing each word of the restaurant’s menu. Why? Because what else are you supposed to talk to a virtual stranger about? Luckily, you can kill two birds with one very stylish stone by sporting a garment or accessory that has a story. “If he’s wearing something that really matters to him — like his grandfather’s watch — those pieces always make for an awesome story,” said Hannah Orenstein, a writer for Seventeen who was previously a matchmaker for Tawkify, New York’s elite dating service. So go head, dear reader: Accessorize with that heritage timepiece or that luxe tie you scored from your European getaway. Not only will  you look good, you’ll also be able to create some extra small talk.

3. Opt for neutral colors

Stick with slightly subdued hues

Stick with slightly subdued hues. | iStock.com

People who can get away with wearing bright colors: children and any 1970s sitcom family. You on your first date? Not so much. While you may love your bright orange and lime green garments, your date can easily interpret these pieces as you craving attention. And dating someone who needs TLC every waking moment seems just as appealing as sitting through a lackluster first date. “An accent print or color may sometimes be a good a thing, but men wearing neons or power-clashing their prints?” remarked Sourbis. “Need I say ‘peacocking’?” Instead, stick with versatile neutrals such as white, black, brown, and gray. If you have a penchant for bright hues, sport a vibrant shirt with an otherwise neutral outfit. After all, that bright red polo will look significantly less flashy with a pair of crisp jeans or khaki pants.

4. Dust off your clean shoes

Luxury brown and black shoes, leather

Wear a pair of good, leather shoes. | iStock.com

Unless you’re taking your maybe love interest on an adventurous hike followed by a romantic picnic — kudos, by the way — donning your dingy gym shoes is never okay for a first date. Sure, they may be comfier than your constricting lace-ups; your over-worn sneakers will tell your date that you’re not taking this meeting seriously. While your date isn’t going evaluate your attractiveness based on whether you’re wearing the latest high-end Italian brogue, but he or she will appreciate that you put the extra effort by selecting a sleeker pair of kicks.

While those work-ready loafers will be perfect for a meet-and-greet at upscale restaurant or bar, don’t rule out your clean pairs of Converse of Vans shoes. If the occasion is right — say, a stroll through the nearest park or coffee — they’d be a great choice. “I honestly wouldn’t mind a guy wearing sneakers to a bar or restaurant on a date as long as the sneakers for fitting for the venue,” said Craig Baldino, a bartender. “There can be ‘nice’ sneakers and that doesn’t have to mean putting your dirty old running shoes on a date.” Regardless of the shoe, make sure your kicks are clean and odor-free before you leave your house. Nobody wants to be labeled as “nice, but had smelly shoes.”

5. Express yourself

Go with fabrics that can layer without adding bulk

Make sure you still look like yourself. | iStock.com

There’s a common misconception when it comes to first dates. Sure, you want to impress your prospective significant other with your good looks, charm, and witty banter; however, it’s important that he or she like you for you are and vice versa. Sartorially speaking, confidence and transparency is key. “It shows that he’s confident in himself and, as we all know, confidence is sexy,” Baldino said. “ I would want him to feel comfortable and to be really himself with me.”

After all, why would you want to date someone who doesn’t even know the real you? If you have a penchant for crisp fascinators and vests, go ahead and pull out your finest pair for the big outing. We know, it’s easy to talk the talk; however, you’re still nervous that your date will cringe at your collection of pocket squares. If you want to tone down your piece, style your sartorial calling card with basic pieces in neutral colors. When worn with a pair of jeans and a T-Shirt, your potential lover may consider your printed blazer a turn on.

Follow Kelsey on Twitter @KMulvs