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What NOT to Wear On A First Date (Unless You Don’t Want a Second Date)

So you’re going on your first date with that awesome girl. Here’s what not to wear to make sure you get a chance for a second.

What Not to Wear on a First Date | Solid Outfit Ideas To Wear Instead

 

1. That Graphic/Statement T-Shirt

Olan Rogers Youtuber GIF via Tenor

Any t-shirt that is emblazoned across the front in large, loud, and brightly-colored imagery or lettering has no room on any date where you’re seeking to impress a girl. You may insist that the shirt in question shows off your personality or some complex aspect of your character. Buddy, if you need a t-shirt to show you have a personality, you might have some issues to work through.

Instead of throwing on your favorite graphic superhero shirt, throw on a clean shirt in a subtle color. It can be a well-fitting button-down shirt in a neutral color. Shirts in subtle colors that fit well give you the right amount of polish, but without looking too indifferent or casual.

2. Ankle-Bearing Anything

man tying his business shoes | What NOT to Wear On A First Date (Unless You Don't Want a Second Date)

Sure, exposed ankles (apparently, they’re called mankles) may look hip and trendy. However, due to its polarizing levels of infamy, you should probably cover them up.

You may rock the mankle look on any other day, but a bare ankle on a first date with a cool girl will leave her mental pictures of those barely-there foot socks she may have used as a schoolgirl. We guarantee you foot socks are sexy to absolutely no one. What’s worse, your girl might even think you’re not wearing socks at all. Sweaty toes will float to her mind. Not an ideal first impression to go for.

If you’re wondering what to wear instead, then consider using regular long socks. Pair them with whatever shoes you prefer to wear. Include bright colors and dare to wear a crazy pattern for brogues, and classic tube socks for more casual shoes. If you’re vertically challenged (read: short), wear socks the same color as your pants. This will give the illusion of length.

3. Office Attire

Unless your workplace has “100% first date friendly” written into its dress code, do not wear your work clothes on your date. You may have the most impressive job in the world, but going on a first date with the same clothes you’ve been sitting around in all day won’t impress. It also carries the risk of making your date feel under-dressed and making you seem like a total square.

You don’t need to bring an entirely different outfit, though. Take a page out of girls’ day-to-night outfit changes where they magically go from office wear to date wear by switching up a few items. You can replace your shirt and tie with a crisp, well-fitted crew-neck t-shirt. Bring trainers or more casual shoes to replace your work shoes, and to finish off a smart, but not a dressed-down outfit.

4. Shorts

Nick Colletti GIF via Tenor

If exposed ankles were a no-no, imagine if you exposed more of your leg. Shorts would be okay for a more chill and casual second or third date—think picnic or a short hike. However, for a first date, wearing shorts just pushes you over the edge and into the ravine of looking like you didn’t put in any effort at all. Shorts are the poster child of laid-back comfort, next to wifebeaters and pajamas—both of which are first-date no-nos as well (obviously).

If you really want to be comfortable on your first date, then wear some comfortable jeans and shoes. It’s okay if you want to be comfy, but for first dates, your focus is to put your best foot forward—fully clothed, preferably.

RELATED: Great First Date Ideas That Won’t Break The Bank

5. A Condom

Condom Im Ready GIF via Tenor

Just…no. If the #MeToo movement hasn’t taught you anything yet, it’s that you should never expect nor assume that getting laid is a guarantee on a first date. Or any date down the pipeline. Sex should come naturally when you’re getting to know each other, or when both parties have actively and enthusiastically voiced out their consent.

Here’s what you should wear instead: some proper human decency.

6. Too Much Fragrance

Stephen Colbert Report GIF via Tenor

Remember in commercials where guys would envelop themselves in a mist of body spray, after which dozens of women make a frantic beeline towards him? That’s fake news. Spraying half a bottle’s worth of aftershave or perfume on your person will most likely send your date home with olfactory damage and memories of a bad date. It may also lead her to believe you didn’t shower and instead covered it up with a fragrance bomb.

Keep things subtle. A mere whisper of fragrance will be most intriguing and have your date subtly leaning in to catch a whiff. With perfumes, seek not to overwhelm, but to intrigue. Great advice, in our most humble opinion.

7. Plunging Necklines

Michael Jackson Rip Shirt GIF via Tenor

Anything from deep V-neck t-shirts or just a couple extra buttons liberally unbuttoned are a no-go zone. Nobody wants a peek into your chest, no matter how structurally impressive it may be, on a first date. Less chest can often be more—besides, a stray chest hair can find its way into your food.

Go for a shallower V-neck if you really must wear one, or a crew cut shirt that fits you well. Go for plain shirts in neutral colors. For button-downs, button up to just below your neck. If your chest is truly impressive, it will show no matter how high the buttons go.

8. Vests

They can be puffy vests, regular vests, or silk vests—if it’s part of a three-piece suit, throw it back in your closet. Not that a formal three-piece suit is what to wear on your first date, to begin with.

If your excuse for wearing a vest is that you want to dress up a casual outfit, just go with a good fitting button-down or plain tee. But if your excuse for the vest is that it’s cold, then carry a jacket with you. A vest is not a perfect means of protection against the cold. What, it’s winter on your torso, but summer on your arms?

9. Flip Flops

Swimming Flip GIF via Tenor

Unless you and your date met on a beach far from the city and decided to have a first date on that exact same beach, put those flip-flops back. Nothing screams “I’m not even trying” as hard as a pair of flip-flops and exposed toes on a first date. Put some good shoes on, for crying out loud.

 

Need more tips? Check out Mathew Boggs’ 10 Great Questions To Ask On A Date:

It’s easy to suddenly be out of outfit ideas for date night, but there are just some items that are best left as far away from your first date prep as possible. Neutral colors may be boring for first dates, but this allows you to work double as hard to let your personality shine through. After all, that’s really what forms the connection that will earn you a second date with your lady friend.

Got any fashion faux pas tales of your own? Let’s have a laugh about them in the comments section below!

Up Next: Questions To Ask On A First Date To Get You A Second

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