First dates for men can be nerve-wracking experience especially when you are just getting back to the dating game or are new at it. Among the few things you can fully control on a first date is how you present yourself on the date. Dressing for success on a first date can significantly up your chances of how good your first date goes. So to help you out here are some of the tips you need to remember on how to dress well on a first date.
As a dating coach, I’ve seen it all: mismatched vibes, over-the-top cologne, wrinkled shirts, and yes, even guys who think sneakers are a universal solution. So let’s break it down. Here’s how to dress and prep for a first date in a way that shows you’re present, intentional, and ready to woe her.
1. Know the Venue and Activity
Before you even actually go on the date you need to know about the venue. Normally it’s you who picks the venue and activity to do together on the date so you choose how to dress up and plan for the date. The date setting will dictate the dress code, so whether it’s a casual coffee date, an arcade date, bowling or darts, or an outdoor adventure, make sure you dress for the occasion.
Example: If you’re meeting at a trendy cafe, a smart-casual look might be perfect—think well-fitted jeans, a stylish shirt, and clean sneakers. Make sure you have accessories that match as well. For a more upscale dinner date, opt for formal shoes, tailored pants, and a crisp button-down shirt.
You get the idea. Dress in a way that suits you for the particular date. Make sure to account for the time as well. If you’re not sure what’s appropriate, ask yourself this: Would I feel comfortable here wearing this? If the answer is “kind of,” keep tweaking. The goal is to look like you belong in the environment but also like you put in a little extra effort just for her.
2. Keep It Comfortable
While looking good is important, comfort is also equally key. If you’re constantly adjusting your outfit or fidgeting you will really look weird and nervous which is the last thing you want to show your date. Choose clothes that fit well and allow you to move comfortably especially if you have a date activity that involves playing together or other activities.
Example: If you’re planning a date that involves an arcade or dancing, walking, or other physical activity, avoid clothes that are not good for movement. A casual, fitted tee with chinos and comfortable shoes would look good. You’ll look sharp without sacrificing comfort.
Tip: Move around a bit in your outfit before the date. Wear it around the house to ensure everything fits well and that you feel comfortable wearing it so there are no issues on the actual date.
3. Fit Is Everything
Here’s a harsh truth: if your clothes don’t fit well, they’re working against you. Baggy jeans? Too-tight shirts? They scream horrible dressing sense. A good fit, on the other hand, shows you know how to look good.
Take the time to try things on before the date. Move around. Sit down. Stand up. If you’re constantly tugging at your shirt or readjusting your pants, it’s going to distract you—and her—from what really matters: your date.
4. Your Personal Style
Your outfit should be the best version of you. But at the end of the day dress in a way that’s an extension of who you are. Your personal style is what sets you apart. Learn what suits you and makes you happy when you see yourself in the mirror.
Dress in a way that represents you. Do you like a classy mafia look or a stylish hip-hop rapper look? Whatever is your style own it. The goal is for you to look amazing for you. Authenticity is attractive. If you’re a leather-jacket-and-boots kind of guy, lean into it. If you’re more of a preppy sweater and loafers dude, go for it. The key is to feel comfortable in your own skin.
That said, there’s a fine line between authentic and lazy. Your favorite graphic tee from college? Probably not the move.
Example: If you’re into vintage fashion, don’t shy away from it. A classic leather jacket or a unique accessory can be a great conversation starter. The key is balance and personal style.
5. Pay Attention to Details
The little things matter in ways you would not normally consider. From matching your shoes and watch with your outfit to that stylish necklace you are rocking. These little things make you look cool. Same with your grooming. A clean, polished look shows where you smell and feel great and can make you 10 times more attractive than you would normally.
I cannot stress this enough make sure to use accessories to look even more stylish. It can be a classy watch, a necklace, or a belt. Whatever you find cool and suits your outfit.
This might seem basic, but you’d be surprised how often it gets overlooked. Grooming is your secret weapon. Here’s the checklist:
- Hair: Fresh cut or at least styled neatly. No bedhead allowed.
- Face: Clean-shaven or a well-maintained beard. Don’t forget a quick nose and ear hair check (yes, it matters).
- Hands: Trimmed nails. They don’t need to be manicured, but being clean and cared for is non-negotiable.
- Cologne: Less is more. A subtle, clean scent is perfect. Don’t marinate in it.
- Watch your socks. If they’re going to show, make sure they match and aren’t overly distracting.
- Accessories. A simple watch or bracelet can elevate your look, but avoid overloading with bling.
- Breath check. Gum or mints are your best friend. Coffee breath or garlic from lunch isn’t a great start to the evening.
Think of grooming as the foundation. You could be wearing the perfect outfit, but if your hygiene is off, it won’t matter. These little touches are things women appreciate a lot.
6. Dress for Confidence
Ultimately, the goal is to wear something that makes you feel confident and the best version of yourself when you go on dates. Confidence is probably the most attractive thing to women, and when you feel good in your clothes, it shows. Choose an outfit that makes you proud when you look yourself in the mirror.
Make sure to wear a perfume that you like and smells great. Here are some recommendations for perfume.
Example: If you have a go-to outfit that always makes you feel great, consider wearing it on your first date. Whether it’s a favorite shirt or a lucky pair of jeans, dressing in something that boosts your confidence.
If you feel you need more help with outfits and dressing well. Reach out to us for dressing tips and grooming advice when it comes to dating and relationships.
7. Be Ready to Adapt
Maybe she’s running late. Maybe the coffee shop is unexpectedly closed. Things happen. Part of being well-prepped is being flexible. Keep a backup plan in your back pocket and roll with the punches. It’s your attitude, that will leave the biggest impression when it comes to handling such situations. Women love a dependable guy.
You keeping things in control and leading the experience will make her feel even more attracted to you.
Conclusion:
Dressing for a first date is about more than just looking good—it’s about feeling good and expressing who you are. Remember, confidence is the best accessory, so choose clothes that make you feel like the best version of yourself. If you are struggling with dating in general maybe its time to get a dating coach to help you level up your dating game.
If you are struggling with fashion and getting first dates we have a special offer for you! To kickstart your dating journey, I’m offering a FREE consultation call. During this call, we’ll discuss your dating challenges and craft a personalized plan to elevate your appeal and success with women.
Don’t let another opportunity pass you by. Embrace the attractive qualities women love and transform your dating life today!
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