woman wearing sunglasses, jeans and a tank top

Single Mom’s How to Pick a Fabulous First Date Outfit

A first date outfit is something that everyone is curious about! And lucky you, you have a date! Woo hoo! Now, what to wear? Read on for some tips and tricks to make him swoon! I should add, these aren't just for first dates, but of course, that first date you want to make a great first impression!

If you're wondering how to *get* to that first date, be sure to check out The Ultimate Guide to Dating as a Single Mom!

Flatter that Body!

Let's start with, a first date outfit could flatter your body! Now, I am not of the mindset that every woman needs to be a certain size or shape. We are all beautiful and can emphasize that with what we wear! If you are being all, but he should love me the way I am…would you go to a job interview wearing scuzzy old pajamas? No way! So dress nicely to feel good and then improve the quality of your date.

V-Necks for a First Date Outfit

Some moms have nursed babies (raises hand) and so have become quite busty! That's great! For real, use it! A v-neckline, whether on a shirt or dress, is one of the best things to do to flatter your decolletage…don't you just love that word?!

Even if you don't have a large chest, v-necks are very flattering on most women!

Photo by cottonbro

Look how beautiful the woman above is, with that v neck and just a bit of cleavage showing! Remember, if you show too much cleavage, the man may have a hard time listening to what you're saying. So, you know, not too much.

Create the Hour Glass Look

Traditionally, an hourglass figure is considered the most desired one. I get it, a lady with a small waist and big hips looks good! But, not all of us have that naturally. We can use clothes to make it seem like we have that shape for a first date outfit!

You can define the waist by using a belt, tucking shirts in. Also, a woman can wear shirts that have darts at the waist, ruching at the waist or sides or ties that tie in back, which nip in the waist. Another idea is doing a color block dress, with darker colors on the outside and lighter colors on the inside. Didn't Kate Winslet do that one time?

Photo by Jenny Uhling

See, you can tell the woman above is wearing a slightly loose top. But, she has tucked the front in and added a belt, defining her waist. Her outfit would be great for a casual or outdoor date, which seems like she may be doing! You go girl! She is even wearing a v-neck!

Solid Colors for a First Date Outfit, No Fresh Prints of Bel Air Please

Here's the thing, I love prints! Absolutely love them! But, when you are first meeting a man, prints can be a bit much. Men are very visual and want to see your shape and prints just confuse the eye. So, if he is an established boyfriend, I'd say go for prints! But for the first few dates, keep it solid, sister!

Photo by Bruno Salvadori

The woman above is wearing a lovely red dress, which is all one color. See how it really captivates your eye, because it is a solid color and stands out? This dress might be too fancy for a first date outfit, but it is a good indication of what color to wear.

About that Color…

Just a brief notes about color, try to find some that complements your skin tone, hair and eyes. You know that favorite outfit of yours, that you always get compliments on? What color is it? Yes, you can do black and black is very sexy but try some of the time to put on some captivating color! It will give you that glow and make you look gorgeous in your first date outfit! Here is an interesting article about color and a first date outfit. Hint: when all else fails, wear red or black!

Avoid Trends for a First Date Outfit

Ok, so for a while now, trends have leaned towards boxy, flowy shirts. I get it, they're cute and forgiving in the tummy area. I like them too! But remember what I said above about how men are visual and need a simple shape of a woman? It's true! So avoid those trends that make your body in a weird shape for a first date outfit.

See example below of what *not* to do

Photo by Dmitriy Ganin

Remember, do not do the above look for a date! I mean, clearly the woman above is very beautiful, I'm not trying to knock her. It's obvious that she can make a sack look good, as evidenced by her…wearing a sack! I'm sorry, but this isn't a great look for a date! Save it for brunch with your girlfriends ok?

What to Wear by Type of Date

Ok, by now you may be wondering but what if I'm doing this activity for the date? Have no fear, Faith is here! Here are some ideas for what to wear, depending on the type of date or type of activity.

Coffee or Dessert…with a Perfect First Date Outfit

This is like a cute but a bit casual date. You can wear nice jeans and a cute top. You don't have to go all out because the guy won't!


Photo by Harsh Raj Gond

The woman above looks casually cool and cute! She is wearing a V-neck tank top and nice jeans. She is wearing solid colors and form fitting clothes that show off her shape! Notice that rust color that looks gorgeous on her…it would look awful on me but remember, how we talked about what colors look good on your skin tone?

Photo by Jep Gambardella

The woman above is wearing a solid color that shows off her skin tone and is cute enough but casual enough for a simple first date outfit. And she is looking happy with a man!

Dinner is Sometimes a First Date

For a dinner first date outfit, you want to dress a little more nicely. Think, dresses, skirts, nice slacks, silks, nice blouse, etc.


Photo by Raditya Narendrasuta

The woman above is wearing a black dress, yes, but it is beautiful and well cut, so her body looks amazing! She has a v-neck too! Dress up a little and a man will appreciate it (you will feel sexier too!)

Photo by Arina Krasnikova

See, the woman above looks cool as a cucumber! She is wearing a luscious shade of green, and this dress would be so cute for a dinner first date outfit in the summer!

Outdoors/Physical Activity…An embarrassing date story!

When you're doing an outside or physical activity, you need to be able to move! I once did an obstacle course date wearing jeans and split the seam by my butt! Luckily, I had a sweatshirt to tie around my waist to hide my butt…it was still embarrassing though. So, don't do what I did, ladies!

Photo by Taryn Elliott

The ladies above and below look super cute but can still move. P.S. Men absolutely love seeing your tush in athletic wear!

Photo by Arina Krasnikova

This would be one of the few times where I will admit, it is ok to wear a hat! If you are doing an outdoor activity and it's sunny, cold, dusty, wet, etc….then, yes you can wear a hat! Notice how her hair still looks good under it 😉 She also has a cute jacket to protect her from the elements and her backpack of essentials, of course. We are all about hiking safety around here haha!

So, What is a Great First Date Outfit?

Let's recap: first, flatter your body, which is typically a v-neck and cinched waist. Wear solid colors and avoid trendy looks.

Second, dress for the occasion…You wouldn't wear an evening gown on a hike! If you're really not sure, you can also ask the guy what he's wearing.

If you want some other ideas, check out this article from Vogue! Keep in mind, they are trying to sell clothes so some of the looks may be more trendy than you need for a first date outfit!

Ladies, if you want to be in the know with my latest dating tips, and freebies, get on my email list! Love ya!