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What To Wear On A Coffee Date: A Walkthrough Guide for Men

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It might seem like gentlemen have it easier than ladies when it comes to dressing up. While women spend hours trying to figure out what to wear, men think they can get away with putting on the first thing they get their hands on. There are, in fact, a few different ways you can mess up and establish horrendous first impressions. 

Coffee shops are one of the most popular places to have first dates. It’s a chill area, there’s almost always Wi-Fi for your phone, and you get to chill over coffee with freshly baked beignets. 

However, figuring out what to wear for these dates can be very nerve wracking, especially if your date is a fashionable lady—or man. 

Here are a couple of outfits that you can throw on for your coffee date.

Kinds of Shirts To Wear on a Coffee Date

Long-sleeve Polo Shirts

Wrangler Authentics Men’s Long Sleeve Sherpa-Lined Shirt Jacket – Photo credit from Amazon

I highly recommend this one from Wrangler. It is very comfortable to use and should be included in your options. Stylish and straightforward, polo shirts are not just easy on the eyes, but they’re also  a comfortable choice. 

For sure, you know how wearing restrictive clothing can be irritating and difficult to sit comfortably in, especially for an hour or two at a coffee shop. Wearing a polo shirt hides the need for such skin-fit clothes. And if the weather is cold, then you’re both stylish and warm. Win win!

Long-sleeved polo shirts can be tied loosely around your waist if the weather gets hot too! If that’s too extreme for you, then try leaving it hung behind you, over your chair. You can keep yourself prepared for whatever weather too, since some polo shirts come with extra pockets. Wallet. Phone. Maybe even a hankie for the lady.

This will be much lighter and more breathable than a heavy winter coat, easier to carry around too. Overall, it combines the features of a button-down shirt with a casual jacket and makes a great solo upper or for extra layers. Plus, wearing a shirt jacket with the right fit brings comfort.

Pair it with jeans, warm-up pants, or shorts, and throw on casual footwear like espadrilles, tennis shoes, or deck shoes for a relaxed vibe. You will definitely look incredible on your coffee date.

T-Shirts

FRTCV Men’s Short Sleeve T-Shirt Casual Tops Tee Classic Fit Basic Shirts– Photo credit from Amazon 

Shirts may not be the most flashy piece of clothing, but that means regardless of your body type, this is a good option for casual occasions. On the off-chance that your coffee date is a little relaxed, a fitted shirt that does not appear to be too tight can look impressive when combined with some decent pants and shoes.

The quality of fabric you’re looking for should be breathable, which means you can stay cool while wearing it in hot weather. If you’re the type to get a little sweaty under your arms, then definitely get a shirt that’s a little loose and breathable. 

One key point about choosing a shirt, any type of shirt, is that you should avoid shirts that squeeze your neck. Being tight around your stomach is embarrassing, tight around the pits? Sweat inducing. But tight around the neck? Prepare to sweat beads down your face. 

There are tons of outstanding outfits that you can incorporate shirts into. And honestly, layering isn’t a problem. Personally though, I recommend that you get a white shirt because that’s a shirt you can never go wrong with and it’s a neutral color that’s perfect for the earthy tones in coffee shops.

Blazer

Amazon Brand – Goodthreads Men’s Standard-Fit Wool Blazer – Photo credit from Amazon

Although blazers are generally geared toward formal occasions, they can be worn for various casual looks too. Your awaited coffee date is one such suitable place. Blazers are refined, classy, yet can pass off for semi-casual wear with the right attitude. The secret to the sauce is being friendly and outgoing. 

Don’t take yourself too seriously, but don’t be too crass or tacky either. If you do go for this look, do it with layers of clothes and leave your buttons open. 

When you find the perfect fit, pair it with denim to appear more laid-back. Chinos work too, they create a smart yet comfortable aura that is barely discernible. You can put a few more layers beneath your top, like polos, shirts, and sweaters.

That look is the perfect way to convince your date to agree to another date. In that case, you should stay relaxed and snug while making a lasting impression as a stylish gentleman worth a legen… wait for it… dary second date with.

Sweater

Yeokou Men’s Casual Slim Full Zip Thick Knitted Cardigan Sweaters with Pockets – Photo credit from Amazon

What’s the long and short of it? Warmth can be achieved through layering on sweaters, as they can be worn over almost anything for a smart look. Sweaters are stylish yet comfortable, with the inside lining being nice and soft. Sweaters are generally thick, so they’re perfect for colder weather and seasons. 

Besides being very comfortable, most sweaters are also lined with a soft inner surface that keeps you dry. Keep in mind that although it is a great sweater, it is not waterproof, so avoid singing in the rain when the drops pour. It’s similar to mock necks in style, except that the collar is attached with a zipper rather than a button. 

Additionally, the classic stand collar is sure to impress your date with your sense of style. This multipurpose backpack is equipped with two slant deep functional pockets, which can store items like a phone or wallet, or even hankies (like a date’s). Basically, you need this overcoat with ribbed collar, cuffs, and hem, which is the ideal windbreaker coat for early spring, late autumn, and winter.You might as well say this outerwear bears the principles of business casual and smart casual.

Wearing high-quality outerwear equipped with layers that fit flawlessly on top, combined with smooth boots and suit slacks will definitely impress your date.

Coat

Chouyatou Men’s Gentle Layered Collar Single Breasted Quilted Lined Wool Blend Pea Coats – Photo credit from Amazon

Wearing a coat to a coffee date on a hot day would be out of the question. But if the weather is nice and chilly or if the date is in the evening, then coats are definitely a great choice. These outerwear clothes are very fashionable, however make sure it’s socially acceptable to wear in your state. 

Don’t be that guy that’s rocking a sick black coat in a town that thrives on shirts, shorts, and slippers.

It’s important to note that if the wrong coat is worn over a suit, it will detract from your overall appearance, no matter how trendy the suit may be. I personally find minimal-looking coats to be the best choice, but a couple extra buttons add some flare too. 

Finally, once you’ve read the social atmosphere and the weather report, checked all the requirements, then you’re ready to bring out a coat. Did I mention that these are the perfect clothes to let your partner borrow if they’re feeling cold? Gentlemen points.

Here Are the Kinds of Pants You Can Wear to a Coffee Date

Jeans

Wrangler Authentics Men’s Classic 5-Pocket Relaxed Fit Cotton Jean – Photo credit from Amazon

You may notice that jeans are one of the most common pants to wear because they are plain in style and can easily match various casual outfits. Great-looking jeans would look swell at a happy hour on a Friday or for a coffee date on a Saturday. 

Jeans have a history that has more depth than most modern pop songs. . It exudes an ethereal air of cool, youthfulness, and urbanity while still remaining undeniably sophisticated. So, depending on the style you choose, you can either be over the top or lowkey.

I suggest pairing jeans with a white shirt and some Adidas. New Balance is a great brand too, perfect for nerds that are also a little athletic..  It’s casual and comfortable, but also sophisticated and straightforward. There are almost no limits to what you can pair with it. 

Jeans are jeans. They’re iconic and will probably go out of the style the day humanity dies.

Straight Pants

Lee Men’s Performance Series Extreme Comfort Straight-Fit Pant – Photo credit from Amazon

In addition to the straight-leg pants, a very popular piece in men’s clothing is the now-in-style chinos. While you may downplay the design as plain and unimaginative, this cut has been a favorite for a long time for good reason. Straight pants are the perfect choice for men who prefer taking every step with class and suave. 

Lee has some of the most comfortable pants on the market, but Uniqlo also has several great stretchy pairs. There are washes ranging from natural to dark, fits ranging from fitted to straight, and sizes for every guy. As straight-cut pants come with a slightly looser fit, styling them requires some discerning.

This garment features an extreme flex waistband and an extreme stretch allowing you a greater range of motion. It is a great pick for coffee dates since it ensures a neat look, as its fabric repels wrinkles. Therefore, if you were nervous and unintentionally moved about, the material would not be crumpled.

A skin-tight T-shirt and minimalist shoes won’t work here, since that comes across as tacky. If everything else remains equal, layer your clothes to add depth but don’t overdress. As for shoes, you can pretty much rock anything except rubber and sneakers—that’s too informal.

Almost any body shape will be nice for this regular cut’s straight-up-and-down design. Yet it especially looks great on a man of a larger frame, as it will give the impression that he is quite tall. Additionally, it features mesh pocketing on the front as well as pockets on the back and is water-resistant, so your hands stay dry whenever you need them. The pockets of this type last longer and continue to perform even when the weather is not nice.

Once that is done, you can just sleeve or pin roll your stitches to the length you prefer and you’re ready to date.

Chinos

Amazon Essentials Men’s Slim-fit Wrinkle-Resistant Flat-Front Chino Pant – Photo credit from Amazon

Assuming you need to look a touch more elegant, we prescribe an easygoing shirt to wear with your chinos. A cloth button-down shirt will supplement your chinos impeccably. Stripes look great, but be sure not to go overboard with bold colors. Match blues with its different shades to keep things on point.

Chinos are generally made of a soft cotton blend of polyamide for added comfort and strength. Although you are moving around a great deal, it will not sag or weigh you down in a tub of leg sweat. 

When it comes to colors, chinos are generally sold in neutral shades to vibrant hues, including tan and navy. Aside from making you more fashionable, the earthly colors match well with most coffee shop aesthetics too. 

If you’re in a rush to go out, then the chinos with a shirt and a pair of clean shoes is a notable combination to throw on. Wearing khaki chinos and a blue or dark overcoat is pretty mainstream too, and looks just as good. On the off chance that it’s rainy outside, put on a raincoat with your chinos. It’s classy and will keep you safe from the downpour. 

Here Are the Kinds of Shoes You Can Wear to a Coffee Date

Canvas Sneaker

Polo Ralph Lauren Men’s Faxon Low Sneaker – Photo credit from Amazon

The canvas sneaker is a trendy shoe that is typically designed for casual wear, making it the best choice for a relaxed date. These shoes are popular for minimal and clean outfits. You’ll find canvas sneakers a common model with brands like Vans, but also with Nike and ASICS.

It’s definitely a shoe that you can wear to a coffee date, paired with chinos and a simple shirt. Alternatively, canvas sneakers look great with black pants too, so a bit of a bad boy vibe is always appreciated. Whatever the case, just avoid wearing baggy pants when wearing canvas sneakers, especially cargo pants.

The vibe between canvas sneaker and baggy pants with pockets falls too close to outdoors camping and doesn’t sit well on coffee dates. Go minimal or semi-casual with these shoes and you’ll surely impress your date.

Loafers

Clarks Men’s Tilden Free Slip-On Loafer – Photo credit from Amazon

For a smart look, loafers in soft suede or leather are perfect for semi-formal outfits.. Loafers generally come in colors and materials that pair well with coffee shops, and the fact that it provides warmth makes it functional on colder weather. It is not only stylish but also very comfortable. At the same time, the smart style will make a great first impression on your date. Therefore, wearing this for your coffee date would knock two birds with one stone, both looking handsomely stylish and impressing your date.It is the perfect footwear for formal yet laid-back folk. You’ll look absolutely classy with these and a pair of chinos or slacks. As for your upper, I recommend something simple, like a shirt or sweater. Shoes make up a lot of an outfit, so you’ll have to be careful with overdressing your shirt.

Loafers add a little more character to your look and are perfect when you don’t want to look too formal but want to stand out. 

Oxford Shoe

Bruno Marc Men’s Oxford Dress Shoes – Photo credit from Amazon

A pair of Oxfords are appropriate for many different formal occasions ranging from days at the office to celebrations with friends and family. Given that they are considered so formal, they need to be accompanied by more relaxed trousers to round out their look. 

Oxfords look great either in black or brown, but dark brown Oxfords would be my personal choice for coffee dates. That way, your shoes match the general color palette of the shop. You can tell a leather shoe is an Oxford model because of the eyelets (where the laces go). 

These shoes have a low heel, simple and classy lacing, and tight stitching at the bottom. It’s also lightweight and flexible so you could do some moderate movement without injuring your feet or your shoe. 

Finally, here’s a pro tip for both the loafers and Oxford shoes. If you want to find one that’s durable, look at the sole of the shoe underneath and inspect it for sewn marks. High-quality leather shoes generally have their soles sewn into the shoe and don’t just rely on glue. 

Accessories You can Wear on a Coffee Date

Watch

Fossil Men’s The Minimalist Stainless Steel Slim Casual Quartz Watch – Photo credit from Amazon

Watches, which are indispensable to any dress code, must be fit to the attire and occasion. We all know that men need women to figure out what to wear on any occasion, but a good watch fits well with most outfits.

There’s an unspoken rule that men can only wear four types of jewelry: necklace, bracelet, ring, and a watch. That being the case, investing in a good watch will go a long way to add to your look.

With a coffee date in mind, a metal or leather watch is a great choice to wear. Leather generally looks more formal but can be dashing in the outdoors. Metal, well, is pretty much a standard and will look good regardless.

Belt

Dickies Men’s Casual Leather Belt – Photo credit from Amazon

While belts are more practical effects than aesthetic ones, if you want to sport a semi-formal look then a good belt will go a long way. Semi-formal outfits where you insert your shirt underneath your pants need a good belt to complete your look. If your watch is gold or silver, it may be appropriate for the belt buckle to follow that color as well. 

For everyone who loves leather, high-quality genuine leather belts look amazing on a belt. They will give you a nice clean look.

Lastly, if the coffee date does get a little more adventurous than a cup of caffeine, then heads up. You can use a belt for some wild activities, given that both of you consent. Or, hey, maybe you want to be the one strapped to the wall too. It’s a free country.

Hats

Hurley Men’s Black Textures Baseball Cap – Photo credit from Amazon

It is no secret that hats are an ever-stylish addition to a man’s wardrobe. They’re also great for any season and no matter what the weather is, a hat keeps you warm, dry, and sun-protected while still looking good.  Hats can be a casual, classy, or eclectic addition to your ensemble.

I don’t recommend that you wear a hat during your entire date, since that would be impolite. However, it’s something you can wear to the coffee shop and away from it, perfect for spontaneous outdoor trips too.

Rings

King Will Dragon Men’s 5mm/8mm Green Carbon Fiber Black Celtic Dragon Tungsten Carbide Ring – Photo credit from Amazon

It’s always a great idea to wear beautiful but not too complex rings like this, as it makes you look cool and mature.

Simple gold or silver rings work well on a man, especially when the colors match the watch. However, going out of the norm with a uniquely designed ring is also a step that your lady might appreciate. After all, it’s not everyday that you get to see something new, especially on something as mundane as a ring.

If you’re a bad boy on your own right, then feel free to sport more than two rings at a time. In fact, you probably don’t need me to tell you that. However, those of your ring first-timers will want to wear just one ring—either on your index or middle finger. Don’t put it on your ring finger, otherwise you’ll look married.

Eyewear

MXNX Aviator Sunglasses MX208 – Photo credit from Amazon

Wearing eyeglasses is a classic fashion trend. There are a multitude of new styles of sunglasses now compared to the large oval lenses of the past. Granted, I strongly recommend against wearing fake glasses just for the aesthetic though. However, you can still sport a fashionable pair of sunnies.

One thing to keep in mind is not to wear sunglasses while having a nighttime coffee date. A pair from Amazon with a composite lens and frames works great for a coffee date, since it will not only give you confidence but it will also give you an impression of being stylish.Wearing shades adds some zest to your outfits that may look cool and smart, depending upon which shape you are wearing. They help complete the vibes of your fashion style and are also perfect for outdoor coffee dates.

You can’t go wrong with a  pair of aviator sunglasses, especially for an open-air coffee date. Additionally, feel free to pick out some square lenses or flashy Ray-Bans if that’s your style.

Additional Tips

Looking for the right outfit for a date can be incredibly stressful, and you might find yourself second-guessing everything you own. The best way to prepare for the occasion is to be yourself and unwind. Particularly for coffee dates, you need to feel relaxed and confident in whatever outfit you choose.

So, decide on a comfortable outfit. Feeling unsettled and out of place with our outfit can easily make you feel less confident.

Another is, the weather should be considered before choosing what to wear from head to toe, so for example, a t-shirt is not the best choice if it’s windy and cold outside. One more thing is to make sure you bring an umbrella with you at all times. Not only do you get home dry, but you also get plus points for being prepared.

Who knows, she might even invite you over her place for being such a gentleman.

Frequently Asked Questions About Dressing for Coffee Dates

How should you dress for a coffee date?

You should wear something comfortable and appropriate for the weather. For instance, you can wear more casual wear like a t-shirt to a summer coffee date and something heavier on colder days. Dress casually or semi-formally, but never too formal.

What should you do on your first coffee date?

Other than wearing a stunning outfit, you need to arrive earlier than your set time. Then, you can ask good questions and listen to your date’s answers. Take the initiative to pay the bill before it arrives, if that’s your thing. And of course, make sure to always be a gentleman.

What does coffee mean for a date?

You can think of a coffee date as a pre-date. It can get awkward and a bit scary to sit across from someone for the first time in person.  A cup of coffee can calm your nerves as you get to know each other better.

A Final Word From The Trending Man

While it takes so much more than an outfit, we hope that you took note of some recommendations and finally have a successful date. It’s worth fussing about the details for the person who could potentially be “the one,” but a coffee date is more relaxed

Be yourself and wear something that’s easy on the eyes, all without looking too sloozy. Have a great date!

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The Trending Man

Our detailed review has been contributed to by multiple members of The Trending Man Review Team to ensure the best research and highest standard of quality. Have a good or a bad experience with one of the products? Please let us know, we love the feedback!

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