First Date Outfit Tips & Ideas (Women LOVE These!) 

I went on my first face to face date ever yesterday at the age of 25 nearly 26. I now have a girlfriend. Thank you Courtney for all of your help. I'm so grateful to you. I really care for my girlfriend so much. Your support helped me.

Courtney, I'd love to see your "how to find a date," like from how to find a girl, how to text her and to set a date, you can make it a series if needed🇵🇭

courtney is the kind of woman that will always wear high heels when going out

A white polo shirt and dark denim looks spot on imo Edit - some other suggestions 1) white shirt black pants and loafers 2) black turtle neck brown pants(lots of mix and matching with colors can be done) 3) any turtle neck and light jacket and dark denim

go for dark denim, withe sneak and a fitting shirt or button-down. remember to do you hair, brush your teeth and please remember to shower before hand

I'm not even seeking a relationship right now but I watch Courtney's videos anyway because they're really enjoyable 😆

I'm going on my first date in two years on Sunday. I'm nervous, but confident. It feels right. Thank you for all the advice.

My first date outfit tends to be darby shoes or simple leather sneakers or boots, chinos, polo or simple button down shirt, and sometimes a tie. That is day or night. Only difference in dressing tends to be more weather related. I have only had a suit to three dates ever. They were not first dates and were cocktail parties with friends.

When it comes to style, I always prefer being overdressed rather than undersressed. I don't always have the opportunity to dress up throughout the day, so when I have the chance to, I take it to look my best. I love it when I have to wear a suit for something special (like a wedding for example), it oozes a certain aura. There's no other clothing item that screams masculinity like a suit and it makes me feel like a real man if you will. Now, for dates, I would always dress it down, with a V-neck or a turtleneck rather than a button-up and a tie, it's just not necessary for the occasion and feels too much like a costume. When I wear a suit, I always feel like a million bucks, and people around me feed off of that energy. That's why I tend to overdress a little bit: it's a great icebreaker, because when a man dresses up for the occasion, she will notice it, and she will be more invested before the date even started

You really give the best advice.. I have a date tomorrow and I couldn’t feel more confident about it because of your videos! 🙂 thank you Courtney! Much support

Courtney, you'd probs agree that the rule-of-thumb is for 1st date outfits could be summed up this way:"Be an extra-well-groomed, polished version of yourself, but neither overly flashy or sloppy!" For years I've adopted the day date attire you've mentioned above as part of my daily outfit i.e. plain/subtly patterned T-shirts & shirts with jeans & dress shoes/boots of tan/chocolate/burgundy/black, though I rarely wear sneakers as they don't really go well with my personality, and never wear heavily-printed T-shirts!

Now you'll have do a video on places to take your date, or conversational faux-pas. Great content, Courtney.

Hi Courtney Amazing video as always and I really like the part where you always suggest to keep it real and authentic😊

Casual: Dark jeans, white tee, black bomber, black sneakers Dressy: Dark jeans, white point collar, charcoal blazer, black chelseas You can conquer 90% of situations, from coffee to bowling to casinos to clubs with either of those styles. The best thing is, they're both super attainable and look great whether you've spent $200 or $2000 on the outfit. Target jeans, Uniqlo tee and bomber, Adidas Stan Smiths? Awesome. Todd Shelton custom denim, John Varvatos tee, Tom Ford leather jacket, Crown sneakers? Sweet. She'll love the look either way. And of course, don't forget the watch. Steel bracelet sports watch/diver for casual, black leather strap for dressy.

First date idea for the homies: drinks right after work. No need to worry about what to wear. Makes it easy for you and the dimey dime you're with.

Courtney your the best for helping us out ima make this outfits thanks for helping look good for the girls 🔥

Will add.... make sure your shoes are polished.... because she will notice....

Saved this video for future references. I think using this as a guide as a starting off point then maybe add a little of my own flavor is what I got from this video.

Wasn’t expecting another video today but I can’t wait to see it when I get home!! ❤️ Have been applying your advice and getting better clothes haha

Love these first date outfit ideas!

Courtney, solid information home girl ! I wear a lot of Ralph Lauren, mainly polo shirts and button downs. Never pay full price, always on sale ! Fit is most important and you can wear Ralph Lauren anywhere, dressed up or casual, and look good. Spend more money on a few colognes, shoes and boots. Every guy should have a few watches and leave the phone in the pocket. Keep up the good work. You’re intelligent, interesting and very attractive. Just being frank with you, pun intended.

I bought more basic tees today. I have Courtney to thank for that ! Warm regards from your northern neighbor !

Between the 30 grand Teddy says I need for a watch collection, and all these date clothes suggestions, y'all are gonna have me cleaned out! lol

Thank you so much I love to watch your videos because it is very helpful and illuminating.

Its great to hear advice from a lady's perspective like you Courtney. I'm happy that people like you exist to also change mens lives. I always dreamed of dating a beautiful lady in high heel boots some day.

Your advice is so useful

Thank you for the video. Loved it😊

Thank you for being in my life! Great advice 👌🏻

Just want it to say Hello, I really enjoy your tips, advices in general everything is very helpful. Ty

great video Courtney keep up the good work

Thank you as always for your input. You are very genuine and it comes across .

Three fits that never fail if you have an athletic body type, the clothing fits, and have the attitude for it- number one, a casual dinner date: Gray fitted jeans, black chelsea boots, a light weight leather jacket, and a white long sleeve t-shirt, (fitted) dress shirt, or polo. Number two, coffee or lunch date: Slim fit indigo jeans, brown boots or monkstraps, and a charcoal long sleeve Henley. Number three, a fancier dinner date: gray trouser, black shoes, fitted navy dress shirt.

Courtney thank you for the tips! I will remember you next time I go on a date lol ☺️☺️

Hey Courtney, can you make one on getting over breakups 😔, your videos seem to help

Dear Ms. Courtney Ryan... Dating co-workers attempted to do that once in life and it became an absolute nightmare because the girl was "between" boyfriends... This was a long, long time ago.... We go through learning lessons in life... Always in Good Taste... CHEERS!! .... Courtney is so cool!

Courtney never misses

i can’t say anything but your comment section is one of the best ones i have ever seen

What dress is best for a black man? Please mention 🎉 And thanks for your simply super explanation. It’s very easy to understand Thank you again

How do we feel about jeans, untucked button down shirt, lightweight hoodie and sneakers? 😆 I’ve not worn it to a date, but so many times I nearly did.

me watching this video feeling nervous even though I don't have any dates planned 😂

I like your ideas Courtney!

Can you do one where girlfriends or sisters can shop for guy clothing? Like what stores to use to find those thing?

Thank You Courtney!! I had a first date today (brunch date) with this girl that im Really into. I watched a lot of your videos in preparation before hand and followed a lot of your advise and the date went Great!! We have a second, more formal date lined up for next weekend. Do you have any Second date videos or tips!? If not will you make one please! Lol. Thank you again, your awesome!

Dammm. Cranking out these videos!!!! Love it

I can tell this channel will be huge!

Thanks so much for all that you do to help us guys struggling with the dating life 😂😊

Would you make a video where you rate viewers outfits out of 10? Killing it with the daily uploads btw Courtney 🔥

I’ve been through both a breakup which was good from a bad ending relationship and then a death of a long time 25 year married spouse but I find a way to go on stay positive and appreciate all your points as I look toward my future Love your videos and help Courtney!!🙂👍❤️ Thank you so much for all your inspiring caring videos 🙂👍🤗❤️

I went out on a date a couple months ago with a girl who was way over dressed for the type of date. I probably could’ve put a little more effort into my outfit, but it fit the scene and I was pretty happy with what I had on. We were just having an early dinner (4 PM) at a very casual outdoor diner that serves burgers and shakes and she showed up in a full dress looking like she was going to an outdoor wedding. I was wearing a plain blue t shirt and a short sleeve button down with a nice pair of shorts and my vans. I feel like it was appropriate. Maybe she over read the situation, I don’t know. She ended up moving out of town anyways the next week for her med school rotations

I'll just buy a costume from party city she's gonna love it 😂😂. Loved the video always great to learn! 🙂

Thank you so much. Your advice has helped me a lot.

I really needed this big thanks to you 💞💞💞

Holy crap you are reading my mind! Thanks Courtney! You rock and your tips are awesome. I’m prepping for a date with a girl and this helped a ton.

You gave great examples, but what about when it is hot out? It is not uncommon to be 110 plus degrees out where i live. Not sure if I can pull off shorts and dress shoes.

thanks for the helpful tips

Classic outfit without classic jacket is so cool on first Date

What are good covid time date ideas? Everywhere is closed and I feel weird saying let's go for a date in the woods lol

I'll wear anything Courtney tells me to :)

5:20 wish I watched this video earlier in November- nothing like spending 130 on a first date to get ghosted haha....love your channel- I updated my wardrobe a bit from your videos and I can feel it making a huge boost already - it’s kind of hard to layer up though when you’re in the Desert 😫😂

LOVE your channel, I'm a guy and you are my HERO! Thank you Courtney! KEEP MAKING VIDEOS! =)

Here in the Caribbean we dress nice on the first date: fittes jeans, dress shirt tucked in, never sneakers, rather dress shoes

What color blaziers would work with oxblood and brown shoes. Take into account the pants will likely be some sort of blue.

we need more girls like Courtney in the world!

So should you wear clothes that you would typically wear to town or wear a dress shirt and dress pants? It'll be a little while before I get the chance to go on a date, but I think I plan on going to a Mexican restaurant for supper (not too fancy, but not fast food either). Or would you say to go in the middle and wear church-type clothes?

Would this suggestion be best for coffee meets with an interest in mind?

Good tips, Courtney!

great content

You forgot to say smell how you look with a great fragrance. 😉

I make and sell tie dye and tend to wear my work everywhere I go (I make sales this way). Would jeans and a tie dye with a flannel work for a day date? Would a tie dye button up work for a night date?

Thanks Courtney!! Though i haven't been on a date yet this really helps make me feel more confident to try it out! One question, is an oversized flanel (jacket) too casual tot wear or is it fine since its comfortable?

I'm a classic person I wear black classic stuff. usually feels good

Gentlemen, “If she doesn’t appreciate the little things, she doesn’t deserve the big thing. “ -C. Ryan 😉

Genuinely didn't know a woman's taste was usually tall, fit guys with tight clothes that layer and stick out that represent our personality with colors like white, black, if semi-formal or blue and tan if casual with haircuts that aren't unusual or under-groomed such as poor hair or untrimmed facial hair. She even spoke out against hoodies, suits and ignored shorts for first dates since a formal date is way too much for a first day which is only meant to last around 2 hours in the first place. If I applied that logic to my room and lifestyle I might even be considered attractive from a stranger's perspective. Thank you so much for this info.

Hey Courtney. What is your opinion about cowboy boots? And what about Timberland shoes? I grew up in Europe, and Timberlands are considered fashion outfit there. But once I moved here to the US I've noticed they are considered work boots.

Enjoyed this video. But I have a question. If my personal style is very easy going/laid back, do I still need to wear all these dress clothes & dress shoes all the time? I usually only wear that for formal occasions. Not restaurants or random nightime dates.

Write that down , WRITE THAT DOWN!!!

Question, I understand the coats and stuff can elevate the style but what do you wear when it’s 90 degrees outside on a dinner date?

You and teddy are my go to guys

Nice collection I am a big fashion fan

1st step, have the body and face of all the male models I reference in my videos. Some reason women LOVE those!

Thanks for giving information I from India....

I like to wear things I'm comfortable in and that I've had girls check me out in. That way I feel more confident.

Common sense stuff I overlooked hope this goes well Saturday.

One question both for chat and Courtney... What is your opinion, should a guy kiss a girl after the date when he walks her home ? (Assuming that date went good and you are positive that she likes you)

HI Courtney - I love your advices, they are so perfect even to become a better person. I am just curious - do you have any professional certification on behavioral science? Thank you once again for your nice videos.

Can't go wrong with cargo shorts lol

Any thoughts on a Man's Spring Wardrobe? Would love a video on it 🤘

She uploaded this at the perfect time for me, lol.

Only youtuber who talks honestly about dating stuff

Thanks for the video!

3:14 Wearing basketball shorts and a t shirt on a first date 🤦🏻🤦🏻🤦🏻 I’m sorry but that’s not a man, that’s a 14 year old trapped in a mans body.

I wish date a girl like you and have your mindset Courtney Ryan 😊😉

So basically wear clean nice clothes and be well put together.

Hi Courtney 😊I would like and you could make a video of what sports or hobbies are attractive in a man that women love !!! Good Luck a hug from 🇪🇨 ❤️🤗....

So wearing my Mickey mouse costume on a first date was a mistake then ! Another good video, thanks for sharing :)

Courtney, who you suggest more on watching TMF, Alex Costa, or Alpha M.?

Don’t forget the daily shower as well guys 🧼

I’ve got some tie dye Crocs, are those acceptable first date footwear?

Morning☀🏡☕☕💛Courtney!!! Afternoon here....In the Valley of THA' 🌵🌴🌞 SUN!!! CLEVELAND,OH....BEEN There many times!!...College Buddies...Where from Cleveland.....WOW!!! I 💙 MA' COLLEGE📚🏀🏈⛳💋YEARS!!! DEM' 1990S!!!! THX💋🌹🏆🎬COURTNEY!!!

thanks a lot