4 Date Night Outfits for Men that Make You Look Too Good to Be True (2024)

February 02, 2023

Written by Jericho Bundac

Image Credit@gabrielhcohen

First dates, third dates, and tenth-anniversary dinners should all have something in common: effort. You want to make an effort and show you care. It means planning the perfect activity, but it also means putting together the ideal outfit. Building date night outfits for men can cause incredible stress to impress.

So, how do you conjure an outfit so your date can’t take their eyes off you? Let's look at four date night outfits for men to inspire your refined attire. We'll follow that up with seven tips that make creating your date night look a breeze.

A Date Night Outfit that Adds a Refined Touch to Casual Activities

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Gap

Who doesn't love dinner and a movie? Elevate yourself for a classic casual date by wearing a date night outfit with some polish. Wear chinos or slim-fit dark-wash jeans with an Oxford shirt. Throw on a bomber jacket to stay warm (and look damn stylish) for an evening stroll after the movie.

Layer Up for an Outdoor Date

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An autumn picnic or outdoor skating in winter are great outdoor dates that help you, and your date connect (or re-connect). The challenge is staying warm. Don't get lost under layers of clothing. Wear pieces made of natural fibres to look polished and feel warm. Wool trousers and a merino cardigan under your coat will make you look refined while keeping you at a warm and inviting temperature.

A Date Night Outfit that Calls for a Suit and Tie

4 Date Night Outfits for Men that Make You Look Too Good to Be True (3)

Aklasu Navy Grenadine Tie

You never want to feel underdressed for an event. When a date calls for a suit and tie, show your date you have James Bond energy in you. Keep it classic and wear a navy or grey suit with a crisp white dress shirt. And when you reach for a tie, leave the duck patterns at home. Channel your inner 007 and choose an understated tie like a navy grenadine.

A Semi-Formal Date Night Outfit that Has Your Bases Covered

4 Date Night Outfits for Men that Make You Look Too Good to Be True (4)

What do you do if you have a date night activity or event where you don't want to look too formal or too casual? The Italians have the style solution for you (don't they always?). Spezzato mixes one suit's jacket with pants from another.

Experiment with separates to find a combination that works for you. A navy blue blazer and light grey trousers go together like whiskey and soda. Wear a refined polo, and you have an outfit your date can't help but admire.

Now that you have some inspiration, it's time to jump into your closet to see what you have to work with. But as you craft your date night outfit, here are a few tips to remember.

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7 Tips You Can't Ignore When Building Date Night Outfits for Men

4 Date Night Outfits for Men that Make You Look Too Good to Be True (5)

1. Dress for the Activity

Always consider the activity and time of day when deciding on your outfit. You wouldn't show up to a Michelin-star restaurant in an outfit for snowshoeing, would you?

2. Wear Clothes that Fit Your Body

Take a look at yourself in the mirror. If you see excess fabric pooling around your shoes or your shirt billowing at the arms, you need to find better-fitting clothes. On the other end of the spectrum, walk around, twist, and reach to ensure your clothes aren't too tight.

3. Keep it Simple (and Sophisticated)

Timeless and understated designs will always make the right first impression. Big logos and loud patterns draw attention away from you. Use clean and sophisticated style, so your date looks at your face and not the distracting designs on your clothing. Speaking of clean...

4. Clean and Press Your Clothes

Wear clean clothes. It sounds straightforward, but it has to be said. Don't wear clothes that merely "look clean." Go the extra mile by ironing dress shirts and pants. The extra effort you put into a crisp white shirt shows you care. But don't stop there.

5. Clean and Polish Your Shoes

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Ideal date night outfits for men include clean shoes. Your shoes will be one of the first things your date notices. Spend a few minutes cleaning your shoes. It's a detail that your date may not think about if they're clean. But they'll definitely notice if you show up in scuffed and dirty shoes.

6. Style Your Hair and Trim Unruly Facial Hair

Putting effort into the details shows your care and respect for your date. Don't let messy hair and unruly facial hair undermine the rest of your look. You want your date to want to look at you—not the person at the other table.

7. Be Comfortable (and Remain True to Yourself)

Aim for clean style, solid fit and comfort in your date night outfit for a guaranteed good time. Wearing uncomfortable clothes that don't feel like you undermine your confidence—and that's something you don't want on a first date, a Valentine's dinner, or casual coffee at your favourite spot.

Building date night outfits for men is not an easy task. But now that you have some info and inspiration, we're confident you'll look polished and feel like the stylish gentleman you are.

Effortless style is about the habits you develop to look refined every day. Discover the 8 Habits of a Stylish Man to look great (and feel confident) from your first date to your tenth anniversary.

Refined essentials that last from first dates to tenth anniversaries.

Navy Grenadine Tie

$85

White Striped Metallic Gold Six-Fold Silk Tie

$115

Navy Blue and Burgundy Block Striped Shantung

$90

Grey Houndstooth Dress Socks

$35

As an expert and enthusiast, I don't have personal experiences or emotions, but I can provide you with information on the concepts mentioned in this article. Let's dive into the different concepts related to building date night outfits for men!

Date Night Outfit Ideas:

The article suggests four different date night outfit ideas for men. Here's a summary of each outfit:

  1. Casual Date Night Outfit: For a classic casual date like dinner and a movie, you can wear chinos or slim-fit dark-wash jeans with an Oxford shirt. Layering with a bomber jacket can add style and keep you warm during an evening stroll after the movie.

  2. Outdoor Date Outfit: For outdoor activities like an autumn picnic or winter skating, it's important to stay warm while looking polished. The article recommends wearing pieces made of natural fibers, such as wool trousers and a merino cardigan under your coat. This will help you stay refined and comfortable throughout the date.

  3. Suit and Tie Date Night Outfit: When the occasion calls for a suit and tie, you can opt for a navy or grey suit with a crisp white dress shirt. To add a touch of sophistication, choose an understated tie like a navy grenadine. This classic look will make a lasting impression on your date.

  4. Semi-Formal Date Night Outfit: If you want to strike a balance between formal and casual, you can try the Italian style of "spezzato." This involves mixing the jacket of one suit with pants from another. For example, pairing a navy blue blazer with light grey trousers can create a refined and stylish look. Complete the outfit with a refined polo shirt.

Tips for Building Date Night Outfits for Men:

The article also provides seven tips to consider when building date night outfits for men. Here's a summary of these tips:

  1. Dress for the Activity: Consider the activity and time of day when deciding on your outfit. Dress appropriately for the occasion to make a good impression.

  2. Wear Clothes that Fit Your Body: Ensure that your clothes fit well. Avoid excess fabric or clothes that are too tight. Well-fitting clothes enhance your appearance and boost confidence.

  3. Keep it Simple (and Sophisticated): Opt for timeless and understated designs. Avoid big logos and loud patterns that may distract from your overall look.

  4. Clean and Press Your Clothes: Wear clean clothes and take the extra step of ironing dress shirts and pants. This attention to detail shows that you care about your appearance.

  5. Clean and Polish Your Shoes: Clean shoes are important for a polished look. Spend a few minutes cleaning your shoes to ensure they are presentable.

  6. Style Your Hair and Trim Unruly Facial Hair: Pay attention to your grooming. Style your hair and trim any unruly facial hair to complete your overall look.

  7. Be Comfortable (and Remain True to Yourself): Aim for a clean style and a solid fit that also allows you to feel comfortable and be yourself. Confidence is key on a date.

Remember, these tips and outfit ideas are suggestions, and personal style preferences may vary. It's important to choose outfits that make you feel confident and comfortable.

I hope this information helps you in building your date night outfits! Let me know if there's anything else I can assist you with.

4 Date Night Outfits for Men that Make You Look Too Good to Be True (2024)

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