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5 Men’s Date Night Outfit Ideas With Shoes to Match


How you dress says a lot about you, especially if you’re meeting someone new. Fashion is a personal thing, and paying attention to the details allows you to present yourself in a way that shows your lucky date who you are — both on the inside and on the outside.

If you’re not typically fashion-minded, you might be wondering if and why wearing dapper men’s date night shoes and sharp clothing matters. Well, it’s not just for you! Whether you’re going on a first date with a crush or a weekly date night with your spouse, putting effort into your outfit shows that you care, and your date will certainly be proud to be seen with a well-dressed man. 

These men’s date night outfit ideas are a great starting point to use for inspiration, but feel free to modify them to fit your one-of-a-kind style. Here are 5 snazzy date night looks to try!

1. Crisp & Clean

When in doubt, you can’t go wrong with a white button-down shirt paired with some chinos, khakis, or even jeans (depending on where you’re going). Match your white top with white shoesdress shoes or sneakers both work — for a put-together look. To pull this outfit off, you must make sure your whites are impeccably clean and don’t forget to press the shirt before heading out.

2. Class Meets Flash

As you brainstorm men’s date night outfit ideas, make sure you dress for the specific event and place. For example, a tailored suit would look fantastic at a fancy restaurant or an upscale lounge, but you’d look out of place at the local dive bar or coffee shop. Of course, if you want to rock your formal men’s date night attire in a casual setting, that’s up to you! Fashion rules are meant to be broken.

If you do plan on wearing a suit (or some other form of formalwear), try sprucing it up with some statement-making shoes — business on top, party on the bottom! One of the best men’s date night outfit ideas is to let your footwear do the heavy lifting when it comes to the flashier pieces in your ensemble. 

For example, trendy shoes in bold colors with decorative features like tassels, rhinestones, glitter, paisley patterns, and other unique designs can add a fun, playful element to your outfit while still maintaining a classy demeanor. Men’s date night shoes with exotic prints can also add some visual excitement to your outfit without compromising the formal look.

3. Sharp but Laid-Back

couple holding hands while sitting

Sometimes you know what type of outfit to wear; other times it’s not quite as clear. For example, coming up with men’s date night outfit ideas can be difficult if you’re doing dinner and a movie. You want to look snappy, but you don’t want your outfit to be too stuffy or uncomfortable either.

This outfit is a fantastic middle ground that looks dapper but relaxed. Start with a patterned short-sleeve shirt with a collar. The pattern is up to you — floral, tropical, flannel, plaid, paisley, stripes…the possibilities are endless. Choose a top that fits your personality. Pair the shirt with well-fitting chinos and some classic brown wingtips or dress boots.

Now that you have the outfit, it’s time to add the finishing touches. While thinking about men’s date night outfit ideas, don’t overlook accessories. Match your belt to your shoes, and tuck the shirt. Cuffing the shirt sleeves can be a flattering look, and you may want to cuff the pants to let your ankles breathe (just make sure you wear some stylish socks that complement your men’s date night shoes). Finally, a nice watch is a great choice to add a finishing touch to your men’s date night attire.

4. Sharp & Sophisticated 

This is another look that’s super versatile — an ideal choice when you want to look put-together, but not overly dressy. Start with a simple collared shirt. Like the vast majority of men’s date night outfit ideas, a collared shirt is preferable unless you’re going somewhere that involves physical activity, or if you’re going somewhere more laid-back like a concert.

Earth tones look great for this look, but anything that’s not too bright should work. If the weather allows, consider wearing a sweater or sweater vest. Pair the top with a complementary pair of slacks or corduroys. For example, if you’re wearing a maroon top, some navy slacks would be a nice match. Finish the look with some dapper monk strap shoes. There’s something about monk straps that are so sophisticated, and they’re a distinctive alternative to the usual dress shoe profile.

5. Sleek & Modern

A couple on a date laughing together

As you brainstorm men’s date night outfit ideas, keep this simple fact in mind: black is always in style and pairs with virtually anything! Black works especially well alongside neutral tones like gray, white, brown, beige, taupe, and cream. A black button-up with some gray slacks and black shoes looks so fashionable and refined. Or, try pairing some black casual boots with slim-fitting black jeans and a black top if you really want to embrace the black aesthetic.

Find the Perfect Men’s Date Night Shoes Now

Just Men’s Shoes is a shoe shopper’s paradise! We offer a huge variety of American-designed footwear at affordable prices. Shop by style or shop by color for more inspiration as you come up with men’s date night outfit ideas. You can also find more fashion tips in our blog. With hundreds of unique styles and a wide range of sizes, we have something for everyone. Ready for a magical date? Put your best foot forward with Just Men’s Shoes!


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