Men’s Date Night Outfit Ideas | Shoe Blog | Just Men’s Shoes (2024)

By JustMens Shoes

Men’s Date Night Outfit Ideas | Shoe Blog | Just Men’s Shoes (1)

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

Men’s Date Night Outfit Ideas | Shoe Blog | Just Men’s Shoes (2)

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

Men’s Date Night Outfit Ideas | Shoe Blog | Just Men’s Shoes (3)

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!

Men’s Date Night Outfit Ideas | Shoe Blog | Just Men’s Shoes (2024)

FAQs

What shoes should a man wear on a date? ›

When in doubt, opting for a dressier shoe is often the safest option. While Oxford shoes and leather brogues are at the formal end of that scale, a more versatile option for any outfit is Chelsea boots or Desert boots.

What should men wear on a date night? ›

Formal Date Night Outfit

For pants, opt for stylish business or dress pants paired with a white button-down. Make sure to add a blazer or dress coat and a clean pair of dress shoes to keep the outfit on point.

What should a man wear on a coffee date in the winter? ›

Sure, it's winter, but do what you can with your outfit to project familiarity and closeness. Try a button-down with the sleeves rolled up, or a sweater that feels soft to your date's touch. For casual winter outfits for guys, Jeans or chinos are perfectly acceptable.

What should a guy wear on a summer first date? ›

For a casual date with no set expectation of attire, like seeing a movie, you want to impress your date without dressing impractically. A classic white t-shirt with jeans is always a solid choice. For a sunny summer day, break out a pair of light-wash jeans and contrast them with black sneakers.

Is it OK to wear mens shoes? ›

Are there any fashion rules when wearing mens shoes? No! Women can wear mens shoes however they like. However, it is important to make sure the shoes fit properly and are comfortable.

How can a man look attractive on a night out? ›

12 Clubbing Outfits For Men To Look Dapper
  1. Black Button-Up Shirts With Gray Chinos. ...
  2. Plain T-shirts With Blue Jeans. ...
  3. Floral Printed Shirts With Trousers. ...
  4. Casual Blazer With T-Shirt. ...
  5. Denim Jacket With Plain T-Shirt. ...
  6. Bomber Jacket. ...
  7. Party-Wear Suits. ...
  8. Leather Boots With Denim Jeans.
Oct 14, 2022

What should men wear to bed at night? ›

Opt for lightweight boxer shorts and a breathable T-shirt – a modern, summery spin on the classic pyjama two-piece set.

What should I wear on a date night with my husband? ›

Cute and casual date night outfits can be as basic as jeans and a graphic t-shirt to dresses and flirty sandals for the ladies. For men, jeans are most common and are easy to elevate with a crisp button-down shirt or a sport coat over a tee.

What not to wear on a coffee date? ›

While some of us tend to look overly sexy on a first date, others tend to be way underdressed. Even if you have a bikini-ready body, do not wear leggings, a hoodie, or your worn-out sneakers on your first date. You'll give the impression that you have no interest in putting forth the effort to look nice.

Should you kiss on a coffee date? ›

The honest answer is: it depends. It depends on the chemistry you and your date have, how the date went, whether the circ*mstances are suitable for a kiss, and most importantly, simply whether you want to.

Do guys kiss on the first date? ›

No, and roughly half of first dates don't end in a kiss. Only about 53% of first dates actually end with a kiss. You should only kiss if it's what you both want. A guy who's truly interested in you will be happy to wait for your first kiss.

Should a man tell a woman what to wear? ›

If your boyfriend has been telling you what you can and can't wear, you may be feeling confused, taken aback, and hurt. It's never okay for anyone to tell you what you can wear, let alone your boyfriend. Everyone has the right to decide that for themselves.

What is a guys ideal first date? ›

A good first date should let you get to know each other without forcing awkward conversation. Taking in a comedy show, visiting a museum, or getting active can help you find some common ground. Try something new together to create space for vulnerability and set the stage for a strong bond.

What shoes are best to wear on dates? ›

Flat shoes like sandals, trainers or loafers work well for a daytime date, while in the evening you may enjoy the confidence boost that a pair of heels gives you. Find out how to choose the best heel height and the best heels for your foot shape.

What do guys want you to wear on a first date? ›

Your outfit should reflect your personal style and provide your date with a snapshot of your personality. Wear something that makes you feel like you, whether that be your favorite color, your go-to cologne, or your lucky pair of shoes.

What shoes should men wear casually? ›

From leather sneakers to sleek driving loafers, these versatile styles will serve you well for just about any occasion on your agenda. What do white sneakers, leather loafers, brown oxfords, and suede boots all have in common?

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