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The Men’s Guide to Date Night Outfits

Everything you need to get ready for date night.

The Men’s Guide to Date Night Outfits

Whether you’re going on a first date or a hundredth date, you’ll want to dress the part. Choose an outfit that matches the formality of wherever you’re headed, and expresses your personality. We’re here to help, and we’ve picked our favorite date night outfits. In addition to outfit ideas, we’ll also share style tips and more expert advice to help you dress to impress. Keep scrolling for our picks and date night style tips.

Our top 5 date night looks

Formal and refined

If you have a formal date planned, definitely step up your outfit and show that you’ve put in effort. You can’t go wrong with a wool blazer and dress pants in a coordinating neutral color—think navy, gray, white, or black. This keeps your outfit grounded and elevated, so the focus is on your conversation and not what you’re wearing. Add a subtle pop of color with a tie and pocket square. Bring it all together with a leather belt and your choice of dress shoes in a rich cognac hue.

Modern sophistication

Meeting up with your date for craft cocktails downtown? You’ll want to put together an outfit that’s elevated, and will be appropriate if there’s a dress code. Choosing a sport coat rather than a blazer dials down the formality a bit, and a pattern like a tonal check shows a little personality. For the perfect amount of polish, add a tie and a pair of derby shoes. If you’re looking for extra panache, a pocket square is a great choice. Don’t feel like it has to match your tie exactly—just make sure they complement each other.

Look smart

To create a polished look that works for a wide variety of date night plans, starting with a windowpane oxford shirt and chinos is a smart choice. If it’s chilly, layer on a sweater for an elevated touch. A fabric like merino wool provides excellent warmth, yet is lightweight and not too bulky. Top off your look with a sport coat in a neutral hue, and add a belt after tucking in your shirt. For the finishing touch, leather loafers are just right.  

Elevated casual

If your date leans more on the relaxed side than the formal side, you’ll want to put together more of a laid-back outfit—but still look put together. Start with a checked button down, and give your blues a break with a colored twill pant. Layer on a neutral sweater in case the temperatures drop. For footwear, a chukka is the perfect in-between shoe that has a relaxed vibe yet is much more polished than a sneaker. And to bring it all together, throw on a sleek leather jacket for a little bit of modern edge. 

A relaxed look

Heading out to a low-key meetup for your next date? Keep your outfit comfy and casual so you can focus on making a connection. Jeans in a darker wash are always a good idea—and a bold graphic sweater with an oversized shirt jacket gives just the right amount of cool vibes. If you’re tucking in your shirt, be sure to wear a belt for a tied-together appearance. And finally, sneakers are a great touch for a casual look. However, make sure they look polished and don’t have any visible scuffs or wear.

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How to dress for a dinner date

Whether you’re meeting for an impromptu lunch or a formal dinner date, chances are you might be wondering how to dress. In fact, 37% of men say they worry most about what to wear when dining with their spouse or significant other.* We know that looking your best is standard, but your dinner date outfit is mostly determined by where you’re meeting.


Casual date outfits

If you’re going somewhere laid-back like a coffee shop or a bar, our favorite men’s casual date outfit consists of dark wash denim and a slim-fit sweater or long-sleeve henley. We suggest going with a great pair of boots instead of sneakers because it showcases effort and helps the dinner date outfit feel a little more special. Don’t forget to add a jacket—a water repellent coat if it’s wet out, or something heavier if it’s chilly. 


Somewhere in the middle

So how do you plan your dinner date outfit if you’re going somewhere that isn’t necessarily formal and not really informal either? It’s probably best to err on the side of caution and go on the dressier side. You can never go wrong with slim or straight-leg chinos and a plaid dress shirt—just be sure to tuck it in and add a belt. For an added layer of polish, consider wearing a sweater overtop. Then complete the date night outfit with suede boots and a statement coat.


Dressed to impress 

A dinner date is the perfect time to pull out all the stops. Don’t be afraid to embrace your inner Bond with a tailored sport coat and crisply pleated dress pants. Style the two with a solid colored dress shirt or something with a subtle pattern for an eye-catching combination. Our secret to giving your date night outfit a magical touch? Finishing off the look with a bold tie and coordinating pocket square for an unexpected pop of color.


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Building a date night wardrobe

Putting together a date night outfit can be anxiety-provoking, but making sure you have a few key items will help you save time when you’re creating your outfit. We’ve rounded up a list of nine essentials that you can always lean on as a foundation for your date night outfits.


1. Suit
A sleek, coordinated suit brings instant sophistication to a more formal date.


2. Sport coat
Dress it up or down—this versatile piece is a true wardrobe workhorse.


3. Button-down
For a step up from a casual date, you can’t go wrong with a crisp button-down.


4. Tie
When in doubt, dress up rather than down. Plus, a tie always fits the dress code.


5. Sweater
You can depend on a classic pullover for smart style and a little extra warmth.


6. Dark jeans
A darker wash brings an elevated feel, while a straight-leg cut always flatters


7. Chinos
These are a nice step up from jeans yet still feel semi-casual and relaxed.


8. Sneakers
Sneakers are a great casual touch, and a rich leather pair offers a refined take.


9. Dress shoes
From a derby to a loafer, a solid pair of dress shoes brings polish to any outfit.

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Three expert style tips

We know you got this, but these tried-and-true tips always apply.

1. Keep it subtle

When choosing your date night outfit, you’ll want to steer clear of busy or garish patterns. The same goes for any pieces with oversized brand logos. If you want to use your clothes to express some of your personality, try adding pops of print or color in smaller pieces like a pocket square or your choice of socks.

2. The perfect fit

What’s equally as important as what you’re wearing? How each piece fits you. Make sure nothing is too baggy or skin-tight. Look for dependable choices like a tailored sport coat, straight-leg jeans, or a slim button-down. Also, getting your formalwear professionally altered is a great way to achieve the perfect fit.

3. It’s all in the details

If you’re wondering what accessories to add, the answer is: Keep it simple. A watch is always a good idea, and there are plenty of options from casual to dressy. For example, one with a metallic band is great for a formal dinner. But if it’s a casual daytime date, you might want to choose a more sporty option.

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Your date night style questions, answered

We’ve compiled answers to some FAQs about dressing for a date night. Click the questions below for more style advice. 

I need an extra layer to stay warm. Can I wear a hoodie?
What about jeans? I feel comfortable and relaxed in my favorite pair.
How should I dress for a date that’s right after work?
What about pre-date grooming?

If you have another kind of date night coming up, talk to a stylist to get a Trunk full of outfits that are just as unique as your plans.