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25 Date Night Outfits for Men (All Year-Round)

14 min

Looking for date night outfit ideas? Check out these twenty-five looks for every season.


Trying to choose the perfect outfit for a romantic date can be a daunting task, especially when it comes to deciding what to wear for your special lady. There are many aspects to consider when advising on this topic. To begin with, it's important to note that the ideal date night outfit varies depending on the following factors.


Every date night is unique; however, it's crucial to dress appropriately. Therefore, considering the time of day, venue, and location of your date are all critical factors to ensure a successful evening out.

If you are going on a date during a cold evening in a place with low temperatures, it's important to prioritize comfort over style. Don't misunderstand; you should remain stylish, but I recommend wearing warm layers to keep yourself comfortable throughout the date. If you live in a place that experiences frequent rainfall, it would be wise to incorporate a rain jacket into your look to stay dry, etc.

Here are twenty-five outfit ideas for men, one for each season, perfect for a date night.



Some may not recommend the combination of denim-on-denim, but trust me when I say it's not as tricky to pull off as it may seem. The key to making this look work is to ensure that the denim upper, usually a jacket, has a contrasting shade of blue to the denim jeans on your lower half.

As you can see from this outfit, I am wearing dark indigo jeans and a much lighter blue denim jacket. To complete the look, you can pair it with white sneakers and a classic white oxford-cloth button-down (OCBD) shirt, which will always look great with a denim jacket or jeans. And don't forget to add a pair of classic sunglasses to your outfit for that extra touch of style!

For eleven ways to style a denim jacket, read this article here.


Blue and green work so well together, especially for men with cool skin tones. This color pairing is analogous, meaning the two colors sit next to each other on the color wheel (see below).

Blue & Green are analogous colors.

I have chosen ivy green chinos, a striped sky-blue and white button-down shirt, a brilliant blue coach's jacket, and a smart pair of German Army Trainer (GAT) sneakers. This is an effective way to add sportiness to an otherwise smart-casual ensemble, perfect for brunch or early afternoon dates.

If you aren't sure what analogous means or want to learn more about color theory, see my article here for an introductory lesson.


Springtime often brings a considerable amount of rain in preparation for Summer. Depending on where you live, a rain jacket might be necessary. In my opinion, a neutral color like tan is the best choice for any raincoat. Neutral colors are easily combined, so you can pair this outfit with another neutral-colored outerwear piece to achieve a harmonious look.

I completed this outfit with classic white sneakers and a ballcap to make it casual and sporty. This look is perfect for casual dates on rainy days.

Read my separate post here to learn why I think neutral colors are best for men's clothing.


White jeans are a classic choice for the Spring season. Pair them with a tastefully patterned crewneck shirt or a neutral OCBD for a stylish look. Regarding footwear, a sleek pair of white sneakers or elegant German Army Trainers (GATs) would be perfect, but don't overthink it! Choose a neutral-colored shoe that doesn't contrast too much with the rest of your outfit.

To take this look up a notch, consider adding a neutral-colored chore jacket or shirt jacket - it will not only elevate your outfit but also provide some extra pockets for your items (or your date's items).

For more information about the best types of Spring jackets for men, read this article here.


Here is a great outfit idea for incorporating a navy blazer into your Spring wardrobe. I have selected a classic blazer in a hopsack fabric that is unstructured and breathable due to its weave. I have paired it with a lighter blue chambray dress shirt and brilliant white denim jeans, making this outfit timeless and tasteful. The chocolate brown loafers add some casual elegance, and the classic shades tie it all together. This look is perfect for more sophisticated outings with that special woman in your life.

Read my article here for twelve ways to style a classic navy blazer.



Here, I'm wearing the same hopsack navy blazer as before with a white crewneck t-shirt, classic khaki chinos, and some German Army Trainers (GATs). Including the GATs is a tasteful way to stand out due to the pedigree of these sneakers within the fashion world and their lux materials. The gray suede paneling in the sneakers offers some nice contrast and some great texture that jives with the hopsack weave of the blazer and leans heavily into the casual nature of this look.

As always, ensure that each garment piece fits and flatters your frame. Ill-fitting clothes, even if the individual pieces are of quality construction, will negatively impact your outfit.

If you need a tailor and aren't sure how to find one, read this article here.


Polo shirts are a Summer essential, and neutral colors are always a safe bet. My favorite is a navy blue pique or knit polo shirt, which is simple yet elegant and has a subtle texture. Navy blue goes well with crisp white, which is why white jeans are also a must-have and can be worn year-round. Finally, including a pair of chocolate brown loafers is a great way to add casual elegance to this classic look.

Read here to learn how to build a capsule starter wardrobe using neutral colors.


If navy blue doesn't appeal to you, black is also a good option for a polo shirt. During Summer, shorts in neutral colors usually work well. Pair it with classic sunglasses and sporty yet elegant sneakers to complete the look. Your lady will appreciate your "brilliance in the basics," even if it's just a casual date.


A shirt with a camp collar is a perfect choice for the summertime. Here is another outfit that is as simple and effective as the previous one. You can wear an olive green short-sleeved collared shirt, navy blue chino shorts, and a classy pair of German Army Trainers (GATs). All you need to complete the look is a stylish timepiece and classic shades.



This type of look is reserved for casual dates. Here is an excellent example of elevating a denim jacket by adding a clean gray oxford-cotton button-down (OCBD) shirt underneath with crimson chinos and sand suede Chelsea boots. Just know that this won't keep you super warm if it's cold where you reside.


This is a timeless and masculine look that never goes out of style. You can't go wrong with a classic brown leather jacket and matching brown leather lace-up boots. For this outfit, I have opted for simplicity by pairing the jacket and boots with black jeans and a black merino wool turtleneck. This look just works and is perfect for occasions that call for a more rugged casual outfit.

However, it's important to note that you shouldn't wear this outfit to a formal event where everyone else is dressed in suits and ties (so be mindful).

To see my six style rules for men, read this article here.


The field jacket is a type of outerwear designed for outdoor activities. It has a military heritage and comes in various colors and materials. For a classic look, you may prefer olive or sage green. The utility is the jacket's main feature, with several zip or snap-button pockets.

Wearing a field jacket can give you an edgy and rugged style while providing ample space for you or your date's belongings. You can pair it with neutral-colored garments like dark wash jeans or suede chukka boots for various date night scenarios. However, remember that this jacket is inherently casual and unsuitable for strict dress codes, such as those enforced in five-star restaurants.


The Fall months can be rainy, just like springtime, depending on where you live. It's important to stay warm and dry during these rainy days. But there's no need to overthink it! Here, I've put together a stylish and functional outfit using neutral colors. The outfit includes a tan "Mac" (rain) jacket, a deep brown quarter-zip sweater, a navy blue dress-collar polo shirt, dark indigo jeans, and brown lace-up boots.

This outfit is perfect for wet autumn date nights, as it is both classy and practical.

If you're in the market for a quality and affordable pair of boots, check out my review of Thursday Boot Company here.


White is a versatile color that looks good all year round and not just during Spring and Summer. Combining a darker shade of red with white creates a stunning contrast.

In this outfit, I have a maroon donegal shawl cardigan sweater paired with a navy blue dress collar polo that complements the tone of the cardigan. The white denim adds a clean look that contrasts nicely with the darker sweater and polo shirt. To complete the outfit, I suggest chocolate loafers and matching navy socks. This ensemble is perfect for a date as it is stylish and dapper yet not overly "loud" or attention-grabbing.


A well-fitting sport coat in a neutral color is always a great choice. In this outfit, I'm wearing a camel flannel sport coat with a black crewneck shirt and dark denim jeans. The olive suede lace-up boots perfectly complement the dark jeans and flannel jacket.

Choosing textures to add extra flair is subtle yet effective, especially when opting for neutral colors. This outfit is perfect for dressing up an otherwise overly casual look with a crewneck shirt and dark-wash jeans while also dressing down a flannel sport coat. This is perfect for a nice date at your local steakhouse or sushi restaurant.

If you want to know the differences between a suit jacket, blazer, and sport coat, read this article here.


When putting together a list of date night outfits, it's important to have an option for wine tasting. Cocktail attire is usually expected for any cocktail event (shocker). While historically, this meant very formal attire, nowadays, a blazer can suffice if paired smartly with additional garments.

I like to wear a navy blazer, a black wool turtleneck, charcoal flannel trousers, and black oxford dress shoes for my cocktail attire. This creates a sleek, dark silhouette that uses tone and texture to create visual intrigue. A black, dark navy or charcoal suit is still more appropriate for some cocktail events, but given how everything has become much less casual these days, a look like this one will do just fine.


Here is another look featuring a classic navy blazer, a gingham-patterned dress collar polo, and a heather gray quarter-zip sweater. I have added a pair of textured dark wash jeans, but the clear statement piece is the pair of oxblood service boots. Oxblood is an uncommon color of footwear today, but I believe it's time for a comeback. Oxblood can replace conventional brown-colored footwear, depending on the shoe style or boot you choose, and enhance your overall look.

Don't sleep on oxblood boots! This look is an excellent example of subtly adding red hues in tasteful and unexpected ways. It's a great look for anyone with a more conservative style and perfect for a lovely evening out to a casual establishment with your date.



At this point, you're well aware that blazers are versatile and can be worn all year round, especially during the colder months. To create the ultimate Winter date night outfit for a nice dinner out on the town, try layering a classic chunky sweater in a neutral color over a blazer. Pair this with elegant flannel charcoal trousers and timeless shoes like penny loafers.

This outfit is sure to impress and keep you warm during the chilly Winter months.


Most men tend to stick with monochromatic colors, which means they wear the same type of color, just in varying shades. This can be an effective and efficient strategy for dressing up.

You can see that I have chosen shades of black and gray in my outfit. The texture in my car coat takes things up a notch because it provides a lot of visual intrigue. I want to draw special attention to the chukka boots; they aren't black or gray but dark olive green in suede. I believe that dark olive suede is the most versatile color and material for boots anyone can wear, and this ensemble is further proof.

This outfit exudes elegance, and as long as the weather warrants something with a scarf, I recommend this look as often as possible.

Read this article here to learn why dark olive is the best boot color for men.


Nobody says you must wear boots all the time in Winter. Despite my love for boots, living in sunny San Diego has taught me that not every day in December is a boot day. Don't overthink it; just make tasteful decisions.

In this outfit, I am wearing a chunky cable-knit turtleneck, a charcoal topcoat, classic blue jeans, sneakers, and a ball cap. If needed, throw on some shades, and you're all set! This is an excellent way to leverage those foundational pieces that every man should own when constructing his initial wardrobe.

To learn more about the best coats for men to wear during the Winter, read my separate article here.


Layering for outfits is best done by starting with thicker layers on the outside and gradually working your way in with thinner layers. This outfit is an excellent example of that. The outermost layer is a charcoal topcoat, which provides much-needed warmth for the brisk weather. The middle layer is a charcoal v-neck sweater, and the innermost layer is a blue gingham dress collar polo. Gray and blue complement each other perfectly, but the oxblood boots steal the show, in my opinion.

For more Fall and Winter date night outfit ideas, check out my separate post here.


If you're looking to own just one topcoat, charcoal is a safe bet. However, for a classic look that's a bit more unique, I suggest a camel coat.

This timeless outfit will always be in style for Winter: a camel topcoat, a black or gray turtleneck, and black chinos or jeans. You can complete the look with black or camel boots, or keep it casual with white sneakers. Either way, it will look stylish and sophisticated.



A navy sharkskin suit paired with dress shoes is a timeless and classic look that works well if you are going to your date straight from the office. If the date you are going on is more formal, you should wear a tie. Conversely, if the date is less formal, you can ditch the tie. Remember to have a tasteful pair of shoes and a nice timepiece (the details matter, after all).

You can read about six different ways to style a navy blue suit here.


Some establishments have an eccentric ambiance where wearing a suit with clean white leather sneakers wouldn't be inappropriate. It's worth noting that wearing a suit with sneakers and a t-shirt can be tricky, but depending on how the suit fits you and where you are taking your lady, it could pay off in the long run.

When it comes to the fit of suit trousers, it is important that they are tapered to your body shape. This means they should be tailored specifically for you, as they rarely fit perfectly when purchased off the rack. Additionally, the length of your trousers should be considered if you want to wear leather sneakers with a suit. Ideally, the length of your trousers should have a slight break or no break to achieve a polished and put-together look.

If you're unsure how a suit should fit properly, check out my comprehensive guide here.


This outfit is an excellent choice for a sophisticated yet rugged look on your date night. Suede is a fascinating and stunning texture that works well throughout the year. This outfit will be perfect for Spring or Winter if you reside in a location like Southern California. It is another example of neutral colors at work, and your date will appreciate it as you lead her through the exciting evening you have planned.


Now smile, open all doors for your date (even car doors), walk on the street side of her, and pay the bill in full. You're lucky to spend time with this woman and ought to treat her like gold. The good news is that you'll be looking like a million bucks and, more importantly, a man who is worthy to be by your date's side. Be confident (never arrogant) and have a good time!

Now go and be the good man I know you to be.



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