What Should You Not Wear on a First Date – 10 Pro Tips

So, you have an upcoming first date! While this can be really exciting, we all get a little bit stressed on date night when it comes time to find that perfect outfit idea. Especially as women over 40 who might be getting back into the dating game after a long time! Remember, first dates are all about first impressions. You want to look cute while dressing for the occasion, and show off your personal style… but you don’t want to send the wrong message by dressing in a way that’s too suggestive or risk putting your date off by dressing too casually.

And sometimes, you’ll have too many outfit ideas bouncing around your head whether it’s a dinner date, coffee date, movie date, casual date – the options can seem endless! Then you throw in the restaurant dress code and it can get really overwhelming. If you are experiencing a bit of first date outfit stress, there’s no need to panic! These 10 tips will help you avoid some of the most common first date clothing mistakes. By avoiding simple outfit mistakes, you will be able to enjoy your date with comfort and confidence!

If you haven’t already, make sure you check out this post with 12 date night outfits for every season!

What Should You Not Wear on a First Date

What Should You Not Wear on a First Date – 10 Pro Tips

Tip # 1 | Avoid Overly Revealing Clothing! 

Remember, you only have one chance to make a first impression. When it comes to first date attire, a degree of modesty can leave your date wanting more, but that doesn’t mean you shouldn’t flaunt your best assets! Choose ONE of your favorite assets and feel free to show off. Are you in love with your shoulders? Wear an off-the-shoulder top! Proud of your toned legs? A cute high-waisted mini skirt or dress is the perfect way to accentuate them. Keep this one asset or one skin rule in mind when choosing your first date outfit.

If you’re searching for chic, affordable date night tops, make sure you check out this post too!


Jimmy Choo Romy pumps

Tip #2 | Skip the Super High Heels (Even the Cute Ones!)

Leave those super high pumps at home, they just aren’t first-date friendly! Even if they are perfect for a night out with the ladies, you want to pull off a sexy, yet relaxed look for a first date. Most of all, you want to be COMFORTABLE! If you’re concentrating on heel-toeing it the entire night, then you won’t be able to act natural and focus on being yourself. Also, we don’t want to wear a pair of shoes that allow for any embarrassing accidents or rolled ankles on date number one! Save the sexy stilettoes for a third or fourth date and sport a nice pair of comfortable shoes, like a cute open-toe sandal, small-heeled pump, or block-heel booties. Two inches or less on a shoe is a good rule to live by for first dates. If you missed my video on shoes that are ruining your outfit and making you look frumpy, make sure you watch that here.

What Should You Not Wear on a First Date

Tip #3 | Ditch the Sweats

This is a fashion faux pas for a first date and if you’re even considering sporting your favorite comfy tank tops and sweats, please think again. Yes, even joggers and sweatpants can be worn to look cute, but not for a first date! You don’t want to give your potential new partner the impression that you’re lazy and sloppy. Even on the most casual dates, a killer pair of jeans, cute and flattering trousers, or a dress is more appropriate. When you get home from your date, you can slide right back into those comfy sweats and let your friends know how it went!

Avoid Too Much Statement Jewelry

Tip #4 | Avoid Too Much Statement Jewelry

Necklaces, watches, rings, and bracelets are essential statement pieces for most outfits, but when it comes to first dates, do not overpower your outfit with too many distracting pieces! Too much jewelry will overwhelm your look and it can distract your date when you’re trying to hold their attention. If you fiddle with things when you’re nervous, stick with less dangly and oversized jewelry; this should help you limit the fidgeting.

What Not Wear on a First Date

Tip #5 | Sheer is Not Your Friend

Okay, don’t get me wrong, I am a huge fan of a sexy sheer fabric. A blouse or cute top with sheer panels? I’m in! But some may say this is a faux pas for first dates. Avoid transparent tops and bottoms for date number one. Remember, there is a time and place for the see-through items, but it’s too risky for a first date and first impression. It may sound a little old-fashioned, but keeping a little sense of imagination will leave your date wanting more!

Tip #6  | Avoid Looking Frumpy!

We all have our favorite old shoes, purses, and jackets. Even though they look a little worse for wear, we just can’t bring ourselves to part with them. Nobody is telling you to throw your old favorites away, just leave them at home for the first date! You don’t want to give off the impression that you’re frumpy or sloppy. Avoid any clothing materials with holes, stains, or pilling. Your first impression should be neat, clean, and borderline professional. That’s a really difficult look to pull off in tattered clothes, even if they are old favorites! Save your old, tattered, worn, and well-loved sneakers for a few dates in when you’re a little bit more comfortable around each other.

I’ve done a couple of videos on how to avoid looking frumpy here and here.


polka dot stockings

Tip #7 | Avoid Fishnet and Patterned Stockings

There is a way to make fishnets and other patterned stockings look adorable, but they don’t belong on a first date. As much as I love a cute pair of stockings, they do come with a little bit of a negative stigma sometimes in the fashion world. If you love the stocking look, go for a darker shade of tights with a cute skirt and boots, rather than a fishnet or patterned look.

Avoid Distracting Patterns

Tip #8 | Avoid Distracting Patterns

I’m not a huge fan of prints. But I do love some bold prints when I’m trying to make a statement. But on date number one, I recommend sticking to simple patterns and solid colors, rather than mixing multiple patterns together. If you want to go for a bold look, wear a simple patterned top with solid-colored bottoms, or a funky-patterned pant with a solid color top. Too many mix-and-match patterns can look overbearing and distracting, plus it’s easy to make them clash! Be aware of whether or not the pattern is bringing attention to an area you don’t want attention. For example, those patterned pants could be really cute…but they could also be making your lower half look larger.

What Should You Not Wear on a First Date

Tip #9 | Avoid Over-The-Top Makeup

For a first date, you want to look like you…just enhanced. Don’t go overboard with the amount of makeup you’re wearing. Your everyday light foundation, contouring, blush, and even red lips are all okay! But putting on extra makeup just because it’s a special occasion could be a bad idea, especially if you haven’t practiced that makeup look before.

orange and blue Staud Ina dress

Tip #10 | Don’t Wear Clothes That Aren’t You!

Be yourself and feel confident! These tips are guidelines and aren’t meant to be more than that. If you don’t agree with something we’ve suggested avoiding, that’s okay. Maybe your “thing” or your signature style involves wearing tons of chunky jewelry…wear the jewelry! The most important thing is to make sure you feel good and be completely and unapologetically yourself. Never be afraid or shy about what other people think about your clothes. They are the number one way to communicate your personality before you get to know someone. Show up on your first date in something that makes you comfortable and lets your personality shine through!

What are some things you avoid wearing on dates? Let me know in the comments! And, KEEP SCROLLING to see some of my favorite date night pieces!

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Date Night Pieces

Sexy Halter
Flattering Jeans
Easy Heels
Perfect Blazer
Glam Sunnies
Chic Ring
Subtle Necklace
Quality Bag
Shade: Pillow Talk
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8 thoughts on “What Should You Not Wear on a First Date – 10 Pro Tips

  1. I was divorced in my 40s and had never dated with a child let alone online. Craziness! After some hiccups at first, I decided that I needed to establish a simple first-date system. I would meet for lunch, coffee, or a one-drink-only, early happy hour. These are ideal situations because: 1. you can wear whatever you wore to work that day (simple, clean, easy to wear, not overly sexy, but tasteful – like the outfits suggested), 2. you can get the heck out of there if 30-60 minutes with the person is quite enough. This approach meant that I also always had an out – have to go back to work, meeting a friend for dinner, have to pick up my child from after-care, whatever. I was never stuck in a bad situation for very long. If the date went well, then I would invest time and effort (cute outfit, a babysitter, make-up, hair, etc) into a second date. If not, then I didn’t lose much time, energy, or money. Dating in my 40s was great fun! I met a lot of neat people, some who are now friends…I also met my wonderful husband and we are loving our 50s together. Good luck! 🙂

  2. Erin, These are Such great tips for dating. I’M at a point where I’m going on some first dates, and these are helpful reminders to Represent myself at my best. Thank you, babe!

  3. Greetings from california! I totally love the look in pic #5. Can you share the Brands for both the top and jean Please?

    1. You have great taste… two of my favorites! Jeans are the “Justine” by Rag & Bone from like 4 years ago, but you might be able to find them on ebay. Blouse is IRO and also sold out, but again, you might be able to dig it up. Erin xo

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