Going On A Date? 8 Things You Should Never Ever Wear

Photo culled from Pinterest

Thigh boot
Thigh boots are a total no no. Josie May, a love and dating coach, points out to me 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
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. "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 says. You'll also be fidgeting and fussing with your clothes, which is distracting for both parties.

Rori Sassoon, an image consultant, relationship expert, and CEO and co-founder of elite matchmaking service Platinum Poire, also points to fit as a critical element of a date outfit. Avoid "something that you can't get into and out of, on your own," Sassoon tells me. "What if you need to go to the bathroom and you can't undo the zipper? What are you going to do? Ask your date to unzip you?"

That sends a message you likely didn't intend. "They are going to think, 'She wants me, and she wants me bad,'" Sassoon says. "Then you're going to have to ask them to zip you back up and you'll look like a tease."

Too loose clothing
If you go the opposite route and wear clothes that are roomy and falling off your body, you can appear sloppy and disinterested in either yourself, 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." Instead, Hall 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!

Brand icons
Avoid icons and brand names, so you don't look like a walking advertisement. Plus, that's all a bit too casual. Author, speaker, and healer Jaya Jaya Myra tells me, "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 furthers, "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."

Slogans
Don't show up to a date wearing silly or corny outward messages on your shirt. Celebrity matchmaker Bonnie Winston reminds me 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," says 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 affect on human behavior while addressing cultural sensitivities and norms. Slogan shirts are so unnecessary in this scenario.

Dirty attire
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 a date: stains on clothes.

Kapur tells me, "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
Professional matchmaker Susan Trombetti draws the line at athletic attire. "Don't ever show up in a date wearing a sports bra," she tells me. "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 I certainly was — Trombetti confirms it's more common than you think.

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

All black
Yes, black is fashionable and slimming. It's also the preferred monochromatic clothing color of many women. But Winston wants you to lighten up.

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