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

Looking great for your date should take some effort–but it doesn’t need to be  hard. Date night outfits for men should take work, but with the right inspiration it can be effortless. Keep reading and put together an outfit that puts the twinkle in your date’s eyes.
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


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

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

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

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.

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

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

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.