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What to Wear on a First Date

What you wear on a date can be important. Date attire requires careful thought and consideration. But we don't mean date night attire for an evening out with your longtime love or significant other. Rather, date outfits for a get-together with a new suitor need to deliberately plan.

You don't want to wear anything too sexy, too thrown together, or too calculated. You want to be comfortable and cute, without being too revealing. You also want to look like yourself. That said, you don't want to send unintentional or mixed messages, either. Obviously, what you wear definitely communicates a variety of things to your date. Selecting your ensemble is of critical importance. Here are all the things that you should never wear on a date — though, of course, it's ultimately up to you.

Reconsider wearing thigh-high boots on a date

Thigh-high boots are a total no-no when you're choosing what to wear on a date. Josie May, a love and dating coach, pointed out to The List that these sexy stompers "may look good when you go out dancing with your girlfriends. But unfortunately, on a date, they give off a hooker vibe." 

You're not going for Julia Roberts in Pretty Woman before she went shopping with Richard Gere's credit cards on Rodeo Drive. You also don't want to send an overtly sexy message that makes you appear too available or — even worse — easy.

Play up your allure and your mystique, rather than strutting around in this sort of attention-seeking (and getting!) footwear.

Too-tight clothing won't be comfortable to wear on a date


Fit is everything. Antonia Hall, a psychologist, relationship and dating expert, and award-winning author, warns against clothes that don't quite fit, especially those that are too small when you're getting ready for a date. "If your clothes are too tight, it tells the person that you have low self-esteem and are trying to gain attention in the wrong ways," she said. You'll also be fidgeting and fussing with your clothes, which is distracting for both parties.

Avoid wearing too-loose clothing on a date

If you go the opposite route and wear clothes that are roomy and falling off your body on a date, you can appear sloppy and disinterested in either yourself or the date — or both. 

"If your clothes are baggy and loose, you'll look like you didn't put in an effort and just don't really care," psychologist and dating expert Antonia Hall said. Instead, she recommends that you "wear something that fits and shows off your figure without being too sexual and you'll make the best impression." 

Baggy may be comfy, but wear something that you love, that fits just right, and shows off the real you!

Clothing with brand icons aren't the best option to wear on a date

Avoid icons and brand names on a date, so you don't look like a walking advertisement when you throw on something to wear on a date. Plus, that's all a bit too casual. Author, speaker, and healer Jaya Jaya Myra told The List, "Never wear clothing that contains slogans or noticeable brand icons. Clothing is meant to be more subtle than that, and properly picked clothing can elevate your ability to communicate with your date."

Plus, you don't want your Hollister hoodie distracting him or communicating with him in your stead. Myra further stated, "You want your date to get to know you without having preconceived notions of who you are before you ever open your mouth — and that won't happen if your clothes broadcast an idea more loudly than your conversation does." 

It's a bad idea to wear clothes with slogans on a date

Don't show up to a date wearing silly or corny outward messages on your shirt, either. Celebrity matchmaker Bonnie Winston reminded The List that no one wants to be the butt of a bad joke, saying, "I had a client who was with a man who bought a shirt on the Venice Beach boardwalk. The shirt said, 'I'm with stupid.' He wanted her to wear it and she said. 'No.' They broke up over it... Not everyone has the same sense of humor!"

"One should not wear slogan tees to avoid embodying the slogan for the duration of the date," said Dawnn Karen, MA, EdMc of the fashion psychology field, a discipline that focuses on the hidden synergy between fashion and psychology and the study and treatment of color, beauty, style, image, and shape and its effect on human behavior while addressing cultural sensitivities and norms. Slogan shirts are so unnecessary in this scenario.

Dirty attire is a big no-no when picking out what to wear on a date

While Vanity Capital's Kaitlin Kapur is "not a fan of telling people what they can or cannot wear because style is such a fun way for an individual to express themselves," there's one thing that's totally unacceptable for people to wear on a date: clothes with stains. 

Kapur told The List, "One thing you should always avoid is clothing that is dirty and or wrinkled." Don't yank clothes out of your hamper. Make sure your date clothes are clean, pressed, and fresh. Dirty and stained clothes can make you appear messy or unkempt in life and love.

Sports bras are not something people should wear on a date

Professional matchmaker Susan Trombetti draws the line at athletic attire. "Don't ever show up on a date wearing a sports bra," she told The List. "Save it for the gym. I don't care if you are meeting for happy hour drinks at the bar next to the gym and you have a great bod. It's not appropriate, it can be too sexy, it can say 'I don't care,' and it's all too revealing at the same time." 

If you are thinking, "Who the hell would wear a sports bra on a date?" — and we certainly were — Trombetti confirmed that it's more common than you think.

Besides, date bras can be sexy and lacy. They can give you confidence, and, if they play peek-a-boo, it's a little tease that adds intrigue and mystery.

Don't be afraid to add color to an all-black wardrobe when deciding what to wear on a date


Yes, black is fashionable and slimming. It's also the preferred monochromatic clothing color of many women. But celebrity matchmaker Bonnie Winston wants you to lighten up when it comes to what you wear on a date.

"Please don't dress as if you're attending a funeral, date, after date, after date," she advised. "The message is very depressing. At least, try to lighten things up with a few colorful accessories." If you're someone who personally abides by an "all black everything" style and is only comfortable in head-to-toe black, don't just nix this suggestion. Try to see Winston's point. We recommend mixing black and gray. That way, you can rock shades of black but you won't give off the goth vibe. Because #compromise.

Maybe skip the tight skirts on date night

Tight skirts are to be avoided on a date, as well, according to Diane Pollack, a wardrobe consultant in New York City. Pollack warns against tight skirts since they can ride up and cause you to be fidgeting with them (and likely being visibly uncomfortable) instead of concentrating on the conversation or how cute your date is.

"Never wear something that is uncomfortable and doesn't fit," Pollack told The List. "For instance, that tight skirt that keeps riding up and you keep needing to pull it down. Or the top that won't stay up and you keep having to pull it up. Or those 'killer' stilettos that are really killing your feet. Basically... anything that you are preoccupied with is going to detract from you being present and having fun on the date."

It's best to avoid distracting prints when deciding what to wear on a date


Distracting prints are no Bueno because they draw attention away from you. Emmy Award-winning stylist David Zyla, author of Color Your Style and How to Win at Shopping, reminded The List, "When dressing for a date, avoid all prints, logos, and anything that distracts from you." As a remedy, Zyla said to focus on particular bodily real estate when choosing what to wear on a date. 

He further noted, "Since most dates are over dinner or drinks, always dress as you would for a portrait, aka from the waist up, employing your most flattering color and a neckline that follows the shape of your jaw. Hint: The most flattering item to wear on a date is a top or dress in your favorite lipstick color, guaranteed to bring out the sexiest, most romantic side of you."

Don't wear things on a date that you wouldn't normally wear

Don't dress for a date like someone a friend wouldn't recognize. In other words, don't present yourself as someone you aren't when picking out what to wear on a date. Rose Jubb, a wardrobe stylist in Portland who specializes in helping women claim more confidence and reach their goals, told The List, "The one thing a woman should never wear on a date is anything that makes her feel like someone she is not. Basically, don't fish with the wrong bait. Be yourself, but the slightly polished version, and you'll reel in the keepers who love you for you."

Dating experts say to not put on perfume before a date


Pause the perfume, people. April Davis, dating expert and CEO of LUMA Luxury Matchmaking, says to nix fragrance when going on a date, which might seem counterintuitive since aromas can be sexy and alluring and can allow your date to remember you. But they can also overwhelm the olfactory sense. 

"Sure, your favorite scent makes you feel like a bombshell," Davis told The List. "But that doesn't mean he will think the same. We're all sensitive to smell and if you chose the wrong scent, you might be risking it all! Save the perfume for when you have your new love interest on lockdown!"

Sweaters aren't the best choice when choosing what to wear on a date

You can end up appearing frumpy if you choose to wear a loose sweater on a date. "A huge attire mistake for a first date — primarily in the fall or winter — is sweaters," dating expert April Davis said. "They're cute and cozy, but they're more of a third or fourth date kind of thing."

Unless you regularly go for that pinup look with a fuzzy, angora fabric, which can be a little too much during the "getting to know you" phase, "sweaters aren't usually form-fitting and can be a little frumpy," she noted. "The first few dates are your time to spark interest," Davis explained. Yes, the mystery is nice, but you don't want to crush their imagination with an outfit their mom might have worn last Christmas."

Don't wear shoes you can't walk in on a date

Marilyn Monroe once said, "Give a girl the right shoes and she can conquer the world." You can wear flats. You can wear heels. Just make sure you wear what you can walk in for your date. 

Personal shopper and expert stylist Jocelyn Kaye weighed in on-date footwear, telling The List, "Nothing kills the mood more quickly than feeling physically uncomfortable. Dates often take serendipitous turns and we find ourselves walking across the Brooklyn Bridge or on a romantic stroll through a park — a little adventure is a true aphrodisiac! Feeling comfortable and confident is key so opt for a kitten or block heel rather than a stiletto, if you go with heels." 

Really high heels can cause trouble on a date

However, if you are a total Carrie Bradshaw and are most comfortable in towering heels, so be it. Just be sure to know what your date has planned since you can't wear six-inch pumps if you're going to be doing a lot of walking. If the date is a surprise, manage your heel height. Fashion blogger Billie Jean Bateson told The List, "The most important thing you should never wear on a date is extremely high heels — above three inches — if you don't know where you will go."

What if your suitor has a romantic stroll planned? Imagine how miserable you'd be in sky-high heels! Bateson continued, "No matter how amazing they look, you have to admit that they are uncomfortable and you don't want to hobble the whole time, especially if he wants to prolong the date and suggests you take a stroll down to the river. It's gonna be a nightmare, believe me!" Wearing comfy shoes means "you can be ready for anything without fear," according to Bateson.

Compromise with a manageable heel height, as recommended by stylist Jocelyn Kaye.

Noisy jewelry can be too loud on a date

Noisy accessories are also not appropriate for a date. Dating and relationship coach Christine Baumgartner believes that what "a woman shouldn't wear on a date is noisy jewelry." Baumgartner explained, "I encourage women to occasionally touch their hair, since men like seeing this, the arm of their date since this breaks the personal space barrier between them and also lets the woman see how she feels when she touches him, and to sometimes use their hands while they talk because it can show how passionate they are about the subject. And wearing jewelry that makes sounds would be very distracting."

Take off your sunglasses before going on a date

The eyes are the windows to the soul, so don't block yourself from connecting with someone on a deeper level by wearing shades on a date. "Everyone looks better in a pair of designer sunglasses, but it stops the one thing you want from a first date: that soul-level connection," said relationship coach Dr. Siva. "If the eyes are the windows to the soul, why hide them? Men tell me that it makes women look unapproachable and also distant. Many of them do not even click on women wearing sunglasses in their dating profiles."

It's been scientifically proven that the whites of the eyes deliver lots of messages. Siva explained, "The sclera (whites) of your eyes are designed to enhance communication with your partner by showing which way you are looking. Studies show we naturally learn this as babies, even before we can speak."

So ditch the Ray-Bans and the Diors if you want to connect for real.

Save the sloppy undies for laundry day, not your date

Carina Pedersen, resident "Knicker Lady" and concierge stylist at [Enclosed], a luxury lingerie company, suggests keeping undies private — but pretty — for your date. 

"Heaven forbid you to show up to a first date in ugly undergarments," she told The List. "You are only doing yourself a disservice, as nothing eats away at your self-confidence like unflattering and uncomfortable knickers. On that first date, you want to feel desirable, attractive, and sensual. The way you feel on the inside projects onto your interaction with your date and a little extra boost of confidence can go a long way."

Throw on some sexy undies, even if it's only you who knows you are wearing them. "Wearing fantastic lingerie under your clothes on a date doesn't have to be overtly sexual, it can (and might) remain your little secret," Pedersen explained. "The bottom line is if you feel empowered and sexy, your partner will notice too."

Yoga pants aren't the right bottoms to wear on a date

The "are leggings pants?" argument is both a raging and prevalent one, with fashion types firmly divided on the issue. That said, leggings and yoga pants are popular. They are also fine for exercise, for running errands, for grabbing coffee with your friends, and for dressing up with an oversized top and heels. They are, however, crossed off the date attire list. 

"Leave the yoga pants at home," said wardrobe stylist Rose Jubb. "Every item of clothing serves a purpose, but I'd never tell you to wear a cocktail dress to Pilates."

On a date, do you, be you

At the end of the day, you can wear whatever you like and are comfortable on a date. Do you, be you. These tips are simply designed to provide some help along the way. Laura Bilotta, a dating coach, and matchmaker in Toronto noted that "deciding what to wear on a date is stressful; you want to look attractive, yet effortless, which is tricky. Ultimately, the number one thing that you shouldn't wear on a date is something you aren't comfortable wearing."

That extends to physical and emotional comfort. "If you're constantly going to be pulling down your dress, checking to see if your bra is showing or not paying attention because your feet hurt too much, then you aren't going to have a good time, and your date probably won't either," she says.

Try your date outfit on and wear it once prior to a date. Test-driving the ensemble will remove the margin for error. "If you're comfortable in the outfit you've chosen, you can relax and focus on your date," says Bilotta.

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