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Writer's pictureC. A. Buttons

How to Dress for a First Date: A Guide for Men

First dates can be nerve-wracking, but one way to ease the tension is by dressing well. Your outfit doesn’t just reflect your style; it shows your date that you’re putting in the effort. The right outfit can set the tone, build your confidence, and make a great first impression. Here’s a guide on how to dress for a first date that’s tailored to impress while keeping you comfortable.


1. Consider the Location

Different dates call for different attire. You wouldn’t wear the same outfit to a fancy restaurant that you’d wear to a coffee shop or a walk in the park. Make sure you know the venue and its vibe before choosing what to wear. Here’s a quick breakdown:

  • Casual Date (coffee shop, casual lunch): Opt for a nice pair of jeans or chinos with a fitted t-shirt or a casual button-down. Add a clean pair of sneakers or loafers.

  • Outdoor Date (walk, picnic, museum): Go for layers. A casual jacket over a t-shirt or henley with dark jeans or chinos works well. Comfortable, stylish sneakers or desert boots complete the look.

  • Dinner Date (upscale restaurant, evening out): Step it up with dressier chinos or tailored trousers paired with an oxford shirt, a well-fitted sweater, or a blazer. Polished loafers or brogues are a safe choice.


2. Fit is Everything

Regardless of where you're going, make sure your clothes fit well. Baggy, ill-fitting clothes can make you look sloppy, while clothes that are too tight can feel uncomfortable and restrictive. Aim for a fit that complements your body shape and allows you to move comfortably.

If you’re unsure, try these simple guidelines:

  • Shirts: The shoulder seams should align with your shoulders, and the sleeves should hit at your wrist.

  • Pants: They should sit comfortably at your waist without a belt and end right at your shoes.


3. Keep It Classic, Not Flashy

While you might be tempted to stand out, a first date is about getting to know each other, not showcasing your boldest fashion statements. Stick with classic colors and cuts—think navy, gray, white, or olive green. If you want to add some personality, do so with accessories like a watch, a subtle ring, or a belt.


4. Focus on Grooming

An outfit can only go so far if your grooming isn’t on point. Make sure to:

  • Trim your nails

  • Style your hair (use a product if it helps keep things neat)

  • Shave or groom your facial hair

  • Check your breath and apply a subtle amount of cologne

A fresh, well-groomed appearance shows that you’re considerate and put together.


5. Prioritize Comfort

You’ll feel more confident when you’re comfortable. Avoid wearing anything you’ll have to constantly adjust or that restricts your movement. Go for breathable fabrics, especially if you tend to get nervous. Being comfortable in your clothes allows you to focus on the conversation and enjoying the date.


6. Don’t Overlook the Shoes

Believe it or not, people notice shoes. A fresh pair of clean, stylish shoes can elevate an outfit, while a worn-out pair can detract from it. Here are some options that work well for a first date:

  • Casual dates: Clean sneakers or low-profile boots

  • Outdoor dates: Comfortable, well-maintained sneakers or boots

  • Dinner or formal settings: Leather loafers, derbies, or oxford shoes

Whatever you choose, make sure they’re clean and in good condition.


7. Pay Attention to the Details

The little things can make a big difference:

  • Wrinkle-Free Clothes: Iron your shirt or pants if necessary.

  • Minimal Accessories: Keep it simple. A classic watch or a small bracelet can look sharp without being over-the-top.

  • Smell Nice, but Don’t Overdo It: A couple of sprays of cologne are more than enough. You want to smell pleasant, not overpowering.


8. Dress Like Yourself

Don’t stray too far from your personal style. If you’re comfortable and confident, it will show. Choose items that you feel good in and that reflect who you are. Trying too hard to be someone else can backfire, and authenticity is always attractive.


Final Outfit Ideas by Date Type

To make it even easier, here are a few ideas based on different types of dates:

  • Casual Daytime Date: Dark jeans or chinos, a white or navy t-shirt, casual jacket, and white sneakers.

  • Outdoor Date: Olive or tan chinos, a henley or t-shirt, bomber jacket, and desert boots.

  • Dinner Date: Tailored navy chinos, light blue oxford shirt, blazer, and leather loafers.

  • Drinks at a Nice Bar: Slim-fit jeans, button-down shirt, leather jacket, and Chelsea boots.


Remember, first dates are about having a good time and getting to know each other. Your outfit should enhance your confidence, not distract you. With these tips, you’ll be ready to make a great impression and focus on what really matters—connecting with your date. Good luck!


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