Dress To Impress: The Best Date Night Outfits for Men

The time is set. The venue has been carefully chosen. Your date is a total smoke show. 

What could go wrong? Besides choking on your salmon or saying "I love you" a little prematurely.

Well, look in the mirror. Are you dressed to impress? Hmm…

If you want to make a great first impression, it's worth putting some thought into your date night outfit. After all, your sense of style says more about you than your dating profile ever could.

To help you put together the perfect date outfit, we compiled this surprisingly entertaining guide.

The 3 Cs: Your date night dress code

The secret to dressing well on date night is finding an outfit that hits three key requirements:

• Confidence: If your outfit makes you feel like a Hollywood A-lister, your date is more likely to see you that way. 

• Class: Dressing for the occasion shows that you're put together and you have a healthy respect for your date. Full marks.

• Comfort: Style is important, but looks aren't everything. Your personality is unlikely to shine through if those tailored pants are cutting off the circulation. (Pro tip: Our Jetsetter Tech pants have anti-ball-crush technology.)

In other words, the perfect outfit helps you impress your date both visually and verbally. 

How to dress for your date

Okay, enough with the corny productivity-bro rules. You get the idea.

To help you apply these principles to the real world, let's look at some actual outfits.

Here's how to dress for various dates.

1. The casual coffee date

So, it's your first date. Or perhaps you just prefer a smaller check.

Either way, you need an outfit that's stylish enough to impress, but relaxed enough to match the leather sofas of your chosen coffee spot. The hot librarian look, basically.

Try something like this:

• Top: Wear a well-fitted, long-sleeve Henley or crisp Oxford button-down in white or light blue. Add a Merino wool crew neck sweater in navy. Pair our Anytime Tee with a Legacy Polo Sweater for a more relaxed look. 

• Bottom: Our Tech pants check the boxes for style and comfort. Choose Oak Khaki or Deep Blue. If you don't have a pair (yet), dark-wash denim should get the job done.

• Shoes: Lean into your casual side with white leather sneakers. Or put on some Chukka boots if you want to look like you know something about wine.

• Accessories: Finish the look with a watch on a leather wrist strap, or slip on a simple silver bracelet. If the weather is bright, add Wayfarer sunglasses.

Pro tip: For your Henley or sweater, tuck just the front edge of your shirt into your pants, leaving the rest untucked. It's casual but polished, giving you a put-together vibe without looking like you tried too hard.

2. The dinner date

This guy means business. He's even made a table reservation (you did, right?!).

Your dinner attire obviously needs to be a little more formal. But there's no need to break out your suit — just follow these suggestions:

• Top: Choose your best dress shirt, ideally in white or light gray. Make sure it's been ironed, we beg. Add a dark blue or green blazer, or slip on a turtleneck if you're dating a sapiosexual.

• Bottom: Here's a surprise: We're going to recommend Jetsetter Tech pants. They're smart and make your butt look pert — elevating your outfit in more ways than one. Choose Space Black or Deep Blue. Tailored dress pants also work just fine.

• Shoes: Go for dress shoes in black or brown leather — Oxfords or Derbys are always a safe bet. If you're in a relaxed setting, suede loafers will add a hint of Italian flair.

• Accessories:If you're ever going to break out that belt with the flashy buckle, now's the time. A silver chronograph watch will show you care about being on time, even if you're delayed.

Pro tip: When wearing a blazer, make sure the shoulder seams hit your actual shoulders and the sleeves don’t extend past your wrist bone. (A slight peek of shirt cuff is perfect.) For shirts, aim for a slim (not tight) fit that’s slightly tapered down the sides — it’ll keep you looking sharp, not boxy. 

3. The activity-based date

You don't have to be sitting at a table to enjoy good conversation. In fact, getting active — even if it's just taking a walk in a well-kept park — can make both of you feel more relaxed. 

And when you get tired, you can sit on a park bench instead.

Here's what to wear for the occasion:

• Top: Our breathable Anytime Tee will keep you well ventilated, so it doesn't look like you're breaking sweat at the mildest incline. Try Charcoal Gray or Bering Sea with a bomber jacket over the top, or our Legacy Jacket in Space Black if you're feeling like a finance bro.

• Bottom: Depending on how athletic you're feeling, you could choose slim fit Tech pants, our Tech Short, or some well-made gray joggers. Neutral colors are your best option.

• Shoes: All-black lifestyle sneakers will add Batman sleekness to your look while being functional enough for any activity. If you're expecting some serious off-road action, you could also try trail shoes in earthy colors — a great way to prove your outdoor credentials.

• Accessories:Grab a baseball cap that doesn't have an oversized foil logo, and throw a slim backpack over your shoulder.

Pro tip: Make sure to dress with layers, so you can peel them off as necessary.

Pro tip two: Bring a change of clothes to look tidy for spontaneous post-walk drinks.

Building your date night wardrobe

These date night outfit ideas are pretty easy to implement if you have all the essential components. 

But maybe you don't.

Not to worry. You're not alone. Many guys get by on the same two pairs of pants for years, much to the disappointment of their potential partners.

If you want to do better, here's a ready-made shopping list for your dating wardrobe.

The core building blocks

It's difficult to build a great outfit without the bare necessities. To make sure you're covered for every occasion, pick up:

• Tech pants: Comfortable, wrinkle-resistant, and stylish for any occasion. Choose Space Black, Charcoal Gray, or Deep Blue for neutral versatility.

• Casual button-up shirt: Lightweight cotton, or linen for warm weather, offers a sharp look. Try to get chambray or something with subtle patterns.

• Henley or crewneck tee: Perfect for layering or wearing alone on casual dates. Stick with solid colors or soft hues for versatility. Choose our Precision Long Sleeve Tee for all-day comfort.

• Blazer: Tailored navy or charcoal elevates any look from casual to classy. Great for dinner dates or dressy outings.

• Leather boots: Classic and sophisticated, perfect for almost any occasion. If in doubt, choose a Chelsea boot in brown or black.

• Classic analog watch: A minimalist design adds a touch of sophistication. Get a leather or metal band to match your personal style.

The fancy investment pieces

Have the basics covered? Now you can start adding fancy extras.

These items will upgrade you from a solid pass to a distinction in style:

• Quality outerwear: We're talking a peacoat or trench coat here. Helps you stay stylish in any conditions. Choose a neutral color so it works for layering over any outfit.

• Fine knit sweater: Merino wool or cashmere adds warmth and style. Perfect for layering over shirts in colder weather.

• Premium sneakers: For when you want to feel hella casual, but look put together. Go for straight white or black unless you're really confident you know what you're doing.

Seasonal options

Obviously, you can't just wear the same outfits all year round. Here are some garments that can help you sweat out the sangria in summer, and avoid hypothermia when the mercury slides south — all while maintaining effortless style:

Spring/Summer:

• Linen shirt: There's nothing more breathable or relaxed. Choose light colors — unless you're a goth.

• Light chinos: An alternative for dates on your yacht. (We're just assuming you have one.)

• Loafers: Speaking of boating, you need a pair of these to complete the waterside look.

• Sunglasses: Because squinting isn't sexy.

Fall/Winter:

• Wool sweater: We like cable knit or ribbed texture. Either way, you're going to be properly insulated.

• Scarf: Wrap up to keep out the frosty wind, and finish with a flourish over your shoulder. 

• Flannel or heavier button-up: Ideal for layering while staying warm. Tartan or plaid patterns add visual interest.

5 men’s date night fashion tactics

Oh, you thought we were done?

No, that was just the ingredients list. 

If you want to master the recipe for great date night fashion, you have to be armed to the teeth with style knowledge. 

Here are the five commandments you'll need for nailing the brief.

1. Try to choose complementary colors

We're all for expressing yourself. But a date night isn't the time to channel your inner rainbow.

Stick to complementary colors that make you look good, not like you got dressed in the dark. Think blues and browns, grays and burgundies, or classic black and white. Unless you're trying to distract her with a fashion disaster, keep it classy.

2. Err on the side of being overdressed 

The dating dress code is a delicate dance. You don't want to show up in a tuxedo for a coffee date, but you also don't want to roll out of bed and call it an outfit.

Consider the venue and the vibe. A little research goes a long way.

When in doubt, err on the side of slightly overdressed. It shows you care.

3. Focus on fit

Fit is king, fellas.

A well-fitted shirt can make you look like you've been hitting the gym — even if your last workout was lifting a coffee mug. Likewise, Tech pants that lift your butt can't hurt.

Sizing is also a key part of the equation. Avoid baggy fits unless your date is blindfolded. Pick garments that fit your form without straining your buttons. Your date doesn't deserve an evening looking at blazer cleavage.

4. Dress appropriately for your age

If there are gray hairs on your head, don't pretend you're 20. Your date is just going to be picturing the "How do you do, fellow kids?" meme while they're talking to you.

Likewise, younger guys don't need to dress like a Dunder Mifflin employee to get respect. Flaunt your youth with class, not immaturity.

5. Don't forget styling and grooming

Remember, the best outfit in the world can't save you from bed head and unkempt nails. Your grooming game should be as sharp as your wit (…maybe a little sharper, actually).

Here's a quick checklist:

• Hair: Styled but not shellacked.

• Face: Clean-shaven or well-maintained facial hair.

• Nails: Trimmed and clean.

• Scent: Present but not overwhelming (she shouldn’t be smelling it across the dinner table).

• Shoes: Cleaner than your browser history.

Ready, set, smooch

We honestly didn't think you would make it this far, but you stayed the course. What a gent. If you can show that kind of grace and apply just half of these tips above, you should be irresistible to your current crush. 

Looking for more style tips? We have a whole library to explore!

And remember to pick up some Tech pants while you're here — they will serve you well, soldier.