14 Style Mistakes To Avoid On A First Date

Don’t worry, you’ve got this.

by Julia Friedman and Claire Fox
Originally Published: 
Here's how to choose a first date outfit.
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Perhaps apart from walking into the first day of high school, getting your first speeding ticket, interviewing for your dream job, and waiting for Harry Styles to take the stage at a concert, there are few things in life that can make a person’s palms sweat more than a first date. Since you can't prepare for most anxiety-inducing date scenarios ahead of time, the best solution is to try to stop thinking about all of the things that could go wrong — it's not worth the energy. One thing that you can control, however, is what to wear on a first date.

It’s incredibly easy to stress out over a first date outfit. You want to make a good first impression, which is totally reasonable. And there are seemingly a million things to overthink when it comes to styling a first date look — heels versus sneakers, hair up or hair down, jeans versus skirt. In the end, it's all about what makes you feel like the most comfortable, best version of yourself.

As personal stylist and co-founder of Ines Adrianna Bojrab tells Bustle, fashion is simply a fun tool to express yourself and stamp your personal identity in a visual way. “Style is your personal brand, and how you dress on a first date not only sets the tone for how others view, respond to, and treat you, but it also has many personal benefits,” Bojrab says. “The age-old adage ‘look good, feel good’ reigns true: When you dress well, you feel more empowered and confident, and consequently, you show up appearing as such, radiating the positive energy you internally feel.”

In terms of what to wear on a first date, there are so many "rules" floating around that it can be hard to parse out the good from the not-so-good. That being said, there are a handful of useful tips that are applicable in almost any first date scenario. Below are 14 style mistakes to avoid, and what to try instead.

1. Buying A Whole New Outfit

When it comes to picking out clothes for a first date outfit, it's likely best to walk a fine line between new and old. Buying something fresh from the store to wear can go one of two ways: It can add extra pressure or feel thrilling, depending on who you are.

Given that, it might be easier to go for something that falls in the middle, with a mix of old and new, as digital fashion content creator Vanessa Chen explains to Bustle. “New can be fun and exhilarating; nothing beats the feeling of going out in a fresh new fit,” Chen says. “With that said, though, it can be risky if you don't feel super confident in a style or piece you've never really experimented with before. So, have the best of both worlds by remixing your wardrobe go-tos with fun, new pieces.”

2. Wearing Something Out Of Your Hamper

Your best bet for a first date outfit probably doesn’t include throwing on the pair of jeans that you've been wearing all week, because chances are, they may have collected a few stains and some stretching. And the same goes for your shirts or dresses that haven’t been worn in a while and are in desperate need of an iron. “It's important that your outfit is freshly steamed and not wrinkled or stained,” says Bojrab.

Instead, wear something fresh. One of the ways to instantly make yourself more attractive to others is to be presentable in your clothing. It’s not so much the label, trend, or level of formality, but rather that your clothes fit well and look clean.

3. Stressing Out Too Much

Perhaps the most important part of your first date outfit has nothing to do with clothes, accessories, makeup, or hair. Instead, it’s headspace. First date stress and nervousness can be difficult to avoid, of course, so you should try your best to minimize the emphasis you put on your outfit for the event. You already likely have other things on your mind to give more attention to, so don’t let the clothes you’re going to wear add to it.

“I think a lot of times people feel more nervous on a first date because the other person has not yet formed an impression of them yet, and they feel pressure to put their best foot forward,” says Bojrab. “While it is important to strive to show up as your best self, I find that being true to yourself and showing up in an authentic way is always [more] impactful and memorable than an outfit.”

4. Wearing Something Complicated Or Fussy

No matter how tempting, Bojrab recommends that you avoid outfits that have lots of bells and whistles. Your most complicated outfit that requires lots of maintenance to wear might not be the one when it comes to a first date. “Don’t wear anything too fussy or new,” she says. “It’s important to be in the moment and… if the date goes well, you don’t want your outfit to be in the way of a spontaneous nightcap or swinging by a house party or concert.”

The same goes for expensive clothing. If you have a piece of jewelry, jacket, or shoes that cost you a pretty penny and are very dear to you, best to skip them on the first date — you never know what a first time going out someone will have in store.

5. Not Dressing For The Occasion

Even if you look great and feel incredibly comfortable in your favorite spaghetti strap dress, a bowling alley might not be the best location for it to shine (your lack of movement might hinder your bowling skills). And the same goes for a nice restaurant: Your favorite frayed jeans and band T-shirt, though comfy, might not cut it for the dress code. Instead, keep in mind what you’ll be doing or where you’ll be going for the date while you choose what to wear on first dates.

“Dressing for the occasion or date activity is probably one of the most important aspects, especially when it comes to comfort,” Chen says. “While five-inch heels might look killer, you'll definitely be regretting them if you're walking around all day. Nothing makes you feel less confident than blisters!”

6. Forgetting About The Weather

Similarly, keep the temperature and time of day in mind when choosing an outfit. If anything, it might allow you to add an extra element to your look, such as a trendy leather or denim jacket. “You can do this by bringing a jacket of some kind with you — even in the summer as the temperatures drop,” Bojrab says. “Dress with versatile pieces to accommodate weather changes or outdoor eating.”

7. Trying Out A Complicated Hairstyle

Unless doing hair is a special talent of yours, spending lots of time on your hair pre-date might not be the optimal way to invest your energy when getting ready. And the same goes for styling it in a way that will require lots of finessing during the date.

“I always think your everyday hair is perfect for a first date,” says Bojrab. “Don’t spend too much time on a style — less is more here.” If you do want to style it a bit, she recommends going for a tousled wave, a half-up style, ponytail, or something else that doesn’t take too much hassle and won’t need adjusting throughout the date.

8. Going Over The Top With Perfume

There’s nothing wrong with having a signature scent, but you certainly don’t want to be wafting fumes (no matter how good they smell) wherever you go like a walking air freshener. “Scent is always memorable, but too much can be overpowering,” Bojrab says. “Spritz once on your wrists and rub together, tapping the side of your neck.” Your perfume shouldn’t be so memorable that it’s the only thing your date remembers from the day or night.

9. Applying Makeup That’s Not You

As with the rest of your outfit, you don’t want what you're wearing in terms of makeup to detract from being your truest self. If you’re someone who wears a bright pink lip and bold eyeliner on the reg, then absolutely show off exactly what you’re all about. But if that’s out of the norm for you, it’s probably best to stay clear of anything extra new. That’s not to say that you should avoid any extra pops of color if it makes you feel fun and flirty. “Keep it to your everyday makeup, or maybe throw on a red lip if you want something a bit spicier (if, of course, snogging is off the table on your first date),” says Chen.

Bojrab has a similar sentiment: “I would opt for your everyday makeup with maybe one additional touch to make you feel special and beautiful,” she says, in addition to playing up your natural features. And, of course, if makeup isn’t your thing to begin with, then just skip it altogether.

10. Adjusting Your Clothes During The Date

No matter how much time you spend getting ready, you always run the risk of a wardrobe malfunction, so it’s best to go for something tried, true, and that doesn’t require readjusting your outfit every few minutes, as Chen explains.

“A great example I can give is, say, a mini skirt that keeps riding up all day,” says Chen. “It's so annoying to have to constantly adjust your outfit, and it really prevents you from living in the moment and getting to know your potential partner better.”

11. Wearing Something Super Tight Or Uncomfortable

First dates can be uncomfortable enough as it is, so why put yourself through the misery of wearing an outfit that is uber tight when you could be wearing something you feel good in? Tight clothes can be especially off-putting to be in if you’re going out for dinner, Bojrab adds. “I recommend staying away from too fitted if you are having a meal and don’t want to be self-conscious or uncomfortable,” she says.

Sexy doesn’t necessarily mean skin-tight, so if something loose makes you feel more at ease, then definitely go for that. But ultimately, whatever makes you feel most confident is the way to go — so if that’s a fitted bandage dress, live your best life!

12. Wearing Distracting Jewelry

Rather than going all out the accessories, Bojrab recommends letting one piece be the star of the show. “Wear your everyday jewelry and make one statement swap — for example, swap your studs with a statement earring that isn’t too heavy or noticeable,” she says. “If you are wearing statement earrings, remove your necklaces and vice versa.

Overall, you don’t want your accessories stealing your personality’s spot as the most memorable thing about you. “Don’t detract from your beautiful energy and conversation with too many busy accessories,” Bojrab says.

13. Having An Unbalanced Outfit

As a stylist, one of Bojrab’s go-to tips is to make sure an outfit is balanced. As an example, she explains, “if you’re wearing a more fitted top, [make sure] that your pants are slightly more relaxed and vice versa.”

And in terms of balanced color, she says when in doubt, go monochrome, which means something along the lines of wearing an outfit of all white, all navy, all black, or whatever color you prefer. “This is the easiest way to look and feel chic, classic, and fresh,” Bojrab says. “The shades of the color don’t need to match perfectly, either.”

14. Wearing Shoes That You Haven’t Broken In

The brand new, sparkling pair of shoes you have might be alluring, especially because they’re so clean and shiny, but you never know how an unworn shoe is going to treat you. Remember, if your feet hurt, you’ll likely have a terrible time no matter how fun the date.

“Footwear being uncomfortable can be the downfall of even the best nights — avoid this by wearing tried and true versatile footwear and unfussy pieces,” Bojrab says. “I don’t recommend wearing something new and not broken-into on a first date.”

15. Dressing Unlike Yourself

If it isn’t clear already, the most important part of your first date outfit is staying true to who you are and having confidence. For Chen, the biggest first date “don’t” is trying too hard to impress the other person or changing your own personal style for their sake. “Don't ask yourself if the other person will like what you're wearing — dress for you!” Chen says. “Authenticity and confidence in yourself is the most attractive attribute, in my opinion.”

As Bojrab puts it, the energy is more memorable on a first date than the outfit, but an outfit can certainly help set the right tone. “I’ve found that people often mirror the self-love and care you have for yourself,” she says. “If you feel confident and respect yourself, you’ll put together an outfit that radiates that energy and others will treat you as such.”

Remember that in the end, it's all about wearing what makes you feel good about yourself. With the right attitude, you can pull off anything — including getting through a bad date. The cliché is true: The most important thing is to just be yourself. Good luck!

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