24 Men’s Date Night Outfits That Look Like He Tried

Most men’s date night outfits come down to trying not to look like he pulled the same shirt he wore to repair the garage (yes, the shirt has history, but not romance). I have outfitted a husband for dinners, concerts, drinks that are adjacent to school events, and restaurants that have menus in a font designed by whispers.

The issue isn’t that men have nothing to wear, it’s that the difference between ‘smart casual’ and ‘regional sales conference’ can be down to one unfortunate shoe choice. These looks are assembled for the real-life calendar, from casual tacos to anniversary dinners, with the right color combos, layers, and shoes that really do the heavy lifting.

1. Navy Knit Polo With Charcoal Trousers

For a comfortable yet polished option, consider a navy knit polo. It provides more structure and shape than a collared button-down but is also more flexible for plans that may involve pasta and require some breathing room. This is a great option for restaurant reservations that are nicer than burger joints but not so fancy that it would be an anniversary dinner.

It does a great job of solving the problem of being too casual or too corporate really well when paired with charcoal trousers instead of jeans. If the restaurant is going to have the air conditioning blasting, you can add a jacket, and with some brown loafers and a simple watch, you are good to go!

2. Forest Green Overshirt With Dark Denim

The forest green overshirt can make any outfit look intentional. Whether or not you spend any time ironing it, it’s a great choice for all of the first date, dinner, or brewery scenarios, as well as for concerts, or casual drinks that lead to fry runs.

It keeps you covered on those days when the weather can’t make up its mind and is a great option to add some structure to a more boring shirt. Best of all, it goes great with dark indigo jeans and some plain tan boots. And no socks, please.

3. Burgundy Blazer With Black Jeans

It is hard to achieve a romantic feel with a blazer that also avoids the vibe of a costume. This is a tough balance to strike, but a burgundy blazer feels romantic. Pair this with a classic wine bar, a cozy jazz club, or any restaurant with mood lighting.

It also alleviates the burden of needing to look dressed up while simultaneously avoiding a full suit. When the color is so rich, you want to keep the rest of the outfit simple. So, a black merino wool sweater, black jeans, and polished Chelsea boots will work perfectly for you.

4. Chocolate Suede Jacket With a Denim Shirt

Suede has a warm and inviting quality, and chocolate suede elevates a simple outfit to a considered one. This works for a steakhouse, speakeasy, or any date where there are wood panels and great fries. It addresses the “I only have casual jackets” dilemma by being relaxed and still sophisticated. For a nice, grounded combination, pair it with a medium blue denim shirt, olive chinos, and dark brown boots.

5. Rust Chore Jacket With a Striped Tee

The rust chore jacket is both warm and gives him personality without having to get into a fashion dissertation. He can wear this when going out for tacos or pizza, at mini golf, on daytime dates, and even when there’s a chance to do some walking.

It helps avoid the awkward situation where a plain looking tee is just a little too plain. For an outfit combo, he can also put this jacket on with a navy striped top, some faded black jeans, and a pair of clean sneakers. Remember, shoe dirt ruins more outfits than most men think.

6. All-Black Denim With a Good Boot

All black looks best when the items being worn have some variety in texture. If not, they may look as if they are there to report for some stage crew duty. This style works well for concerts, standup comedy shows, dive bars and late night dinners.

This black outfit is ideal for when you want to look cool without putting in any effort. An example outfit could be as simple as a black denim jacket over a black t shirt, some straight black jeans, and leather boots which are clean enough to not repulse other people.

7. Teal Cardigan With Gray Trousers

This deep teal cardigan is soft, yet it looks better than most sad office cardigans and also does not look slouchy. Whether you’re heading on a date to the museum or grabbing coffee that turns into lunch, this is the perfect cardigan to wear while you’re wandering at the bookstore. You can look approachable, yet put together at the same time.

Paired with a white Oxford, gray trousers, and dark loafers this cardigan really does look amazing. Just make sure to leave the top button undone so he doesn’t look like he’s defending a thesis.

8. Olive Field Jacket With a Chambray Shirt

Olive field jackets are practical and versatile, similar to a cast-iron skillet, and work as a great piece of outerwear. Field jackets can be worn to farmer’s markets, casual brunches, outdoor festivals, or simply walking to get coffee.

It solves the weather inconsistency problem while keeping the look clean and polished. To create a polished outfit that can transition from running errands to a date, pair the jacket with a chambray shirt, charcoal jeans, and brown lace up boots.

9. Plum Turtleneck With a Dark Topcoat

A plum turtleneck is simply elegant and doesn’t require a tie, meaning it makes everyone’s evening better! Great for winter dinners, theater evenings, or dates at hotel bars, it helps with the issue of formal dressing being dull. When combined with a black topcoat, dark gray trousers, and leather dress boots, you have a very nice outfit for the romantic, colder seasons.

10. Cobalt Camp-Collar Shirt With Tan Trousers

The cobalt camp-collar shirt gives a whole summer date vibe while also avoiding looking like holiday merchandise. Wear it for oceanside evening drinks, dinner, or warm nights, and this shirt is perfect for when sleeves feel like a punishment.

It also solves your problem when a “nice shirt” becomes too stiff and uncomfortable in the hot weather. For the full outfit look, wear with tan pleated trousers, a brown woven belt, and real suede loafers as opposed to flip flops that are trying to act like shoes.

11. Camel Topcoat With a Black Crewneck

I like that a camel top coat can elevate otherwise basic outfits. That’s why I forgive it for being a little extra. Perfect for fall or winter dinner dates, especially those that require walking by valets and involve chilly breezes.

This will also help combat the problem of a puffer coat hiding your good outfit. A good high-low combo would be this coat with a black crew neck, some dark denim, and black chelsea boots.

12. Sage Linen Shirt With Brown Chinos

A sage linen shirt has that fresh feeling; wrinkles come with the shirt and are part of the deal. Waterfront lunches, vacation dinners, and warm-weather dates where nobody wants to look steamed are all great opportunities to wear this shirt.

It helps him stay cool and look like he changed out of his yard clothes. For the full look, combine the shirt with tobacco brown chinos, leather sandals, and some sunglasses that aren’t stuck on the back of his head.

13. Charcoal Suit With a Knit Tee

Wearing a knit tee instead of a button-down shirt can change the office vibe of a charcoal suit. This can be worn to cocktail bars, milestone birthdays, anniversary dinners, and even date night if pictures are on the agenda. Problem solved if you need something “formal but not job interview” and with an ink blue knit tee and black loafers. Add a pocket square if he won’t be fussy about it all night.

14. Brick Red Cardigan With a Denim Jacket

A denim jacket against a brick red cardigan adds warmth and pops of color to your look without the layering feeling too fussy. This look is good for a movie date, or casual dinner or a night that is just for hanging out, but you want to look put together.

It is the answer to “Are you wearing that hoodie again?” Pair this outfit with navy chinos and brown sneakers, just keep the cardigan in a fine gauge to avoid the wrapped for shipping look.

15. Midnight Blue Leather Bomber With Gray Jeans

If you think black is too predictable of a style choice, a midnight blue leather bomber is a strong alternative. It is a versatile piece as you can wear it for cocktails, late dinners, or even dates if you plan on walking through the city.

It also solves the issue of casual jackets looking too youthful or rugged. Clean up the look and make it slightly moody by adding a charcoal henley, gray jeans, and black boots.

16. Mustard Sweater With Navy Trousers

A mustard sweater is fun without being silly, which is a rare and useful flex. It could be worn for brunch, daytime dates, casual holiday outings, or coffee with real chairs. It solves the problem of winter outfits becoming a parade of gray fabric. You can pair this sweater with navy trousers and some brown loafers and a simple belt so the sweater can do its sunny little job.

17. Slate Shacket With Black Chinos

A slate blue shacket is the perfect date night outfit because it’s the perfect combo between a shirt and a jacket. This makes it great for arcade bars, casual dinners, bowling, or anything where you’re going to be moving a lot to avoid the problem of outerwear being too heavy to wear indoors.

This works because of its in-between nature of being a shirt and a jacket. Pair the shacket with an oatmeal thermal, black chinos and light gray sneakers that are clean looking and not “still structurally sound.”

18. Wine Velvet Blazer With a Black Shirt

While you won’t wear a wine velvet blazer every Tuesday, there’s a time and place to wear one, and it could be to a holiday dinner, New Year’s celebration, gallery event, or, in a darker setting, perhaps a date at a romantic restaurant.

It takes care of the problem of party dressing looking too boring, or like you rented it. Team it up with a black dress shirt, black pants, and smart loafers, and as for the rest, keep it quiet. Velvet has the mic already.

19. Espresso Knit Blazer With a Printed Shirt

The espresso knit blazer provides the comfort of a cardigan while maintaining the style of a jacket. Wear it for tapas, first dates, double dates or any dinner where a full blazer feels dead.

It answers the “I want to be able to move freely, but don’t want to be wearing sweatpants” dilemma. For texture without the clutter, combine it with a small scale patterned shirt, dark green trousers and brown derbies.

20. Pine Green Sweater With Black Denim

A pine green sweater is perfect for those winter themed parties without going overboard. Wear it on outings for drinks, dinner parties, trips to the cabin, and any casual holiday dates. The pine green color avoids the Christmas novelty prints that we all know go poorly by dessert. If the weather is cold enough, throw on a wool coat, and for the bottoms, wear black denim and tan suede boots.

21. Clay Corduroy Blazer With a Navy Tee

A corduroy blazer in clay color brings interesting texture and slight 1970s flair without making him look like a movie extra from a record store. He can wear it to local bistros, casual anniversary dinners, and fall dates. It also solves the issue of a blazer looking too polished for a casual eatery. For a cozy yet refined look, combine it with a navy t-shirt, dark brown leather sneakers and jeans.

22. Terracotta Linen Suit With a Cream Knit Shirt

A terracotta linen suit is warm and handsome in a non-circus-master kind of way. Destination dinners, summer weddings that have a date-night vibe, rooftop parties, and anniversary trips all beg for this suit.

It answers the question of what you should wear when you don’t want a stuffy navy business suit. To complete the look, wear a cream knit shirt, dark brown loafers, and skip the tie. The suit knows why it’s there.

23. Aubergine Overshirt With a Black Tee

An unexpected yet easy option to wear is an aubergine overshirt. This is particularly useful for men who fear that the word “color” means circus. It could be worn to indie films, informal cocktails, concerts, or dinner dates.

This aubergine overshirt really helps with the problem of neutral outfits that are feeling just a bit flat. Combined with a pair of black leather sneakers, a black t-shirt, and washed gray jeans, the overshirt allows the purple to remain grown-up.

24. Black Turtleneck With Gray Wool Trousers

A black turtleneck and gray wool trousers are classic, sleek, and a little bit mysterious (in a good way). This outfit is versatile enough for gallery openings, theater dates, hotel bars, or dinner reservations that leave you questioning the dress code (think real cloth napkins).

This look solves the problem of wanting to dress up without having to wear a dress shirt. To complete the look, add oxblood loafers and a tailored coat as the shoes will elevate the outfit and ensure you don’t look like a philosophy substitute teacher.