Best First Date Outfits for Men | The Ultimate Guide
If you’ve been absent from the dating scene for some time, preparing for that all-important first date can prove daunting. For many men, deciding on what to wear on a first date is a major issue. Selecting a killer first date outfit is even more important if you’ve agreed to a blind match. If they’ve never seen you before (like on a dating website), your date outfit is going to go a long way in forming the first impression. Only spoken with a prospective date online? If you’ve relied on dating apps (like Tinder or Ashley Madison) to connect with singles, your outfit ideas are going to need to reflect the personal style you’ve presented on any dating profiles.
Best First Date Outfits for Men
Thankfully, dressing for a first date is easier than you might think. However, to make the best possible first impression, you’ll need to take a step back and consider the kind of date you’re heading off to.
Where Are You Meeting?
Date venues will go a long way in informing your date outfit choices. Have you agreed to meet in a fancy restaurant? If the answer is yes, dressing casually is probably out the window. Instead, you’ll be looking at a dress shirt, dress shoes, and tailoring as standard.
Made plans for a more casual first date? Unless you’re meeting at a dive bar, you’ll probably want to forget about wearing white sneakers and graphic tees. Instead, take the smart casual route. Combine Chelsea boots with straight leg jeans and a pique polo shirt. A versatile ensemble like this one will see you right, no matter where the evening takes you.
When Are You Meeting?
This is another important thing to consider before settling on your first date wardrobe. If a busy schedule means you can only meet someone during the day, you’re going to have to rethink your outfit choices. Will you be heading out from the office for a lunchtime meeting? If you’ve agreed to a casual date with midday drinks, make sure you’re dressed for the occasion.
If your standard work attire is fairly formal, think about adopting a more casual look that morning. This way, you’re not going to create a false impression of yourself when meeting. Ultimately, the best advice is to wear clothes you feel comfortable in.
Always Choose Flattering Fits
When exploring date outfit ideas, don’t forget the importance of fits. More men are embracing tailored shirts and slim fit denim, but there are plenty of guys out there who are happy to reach for baggy jeans and an ill-fitting t shirt.
Even a basic tee should fit your body shape perfectly. It’s worth spending a little more on wardrobe staples to show off your body in all its glory. If you’ve penciled in a more formal date, you’ve ample choices when it comes to flattering tailoring. If you’re investing in new clothes for the date itself, try and avoid shopping online unless you’ve purchased items from that retailer before. Garment sizes can vary widely between retailers and if you’ve left it to the last minute, you won’t be able to return your order.
Ideally, you should be heading out to stores where you can actually try clothes on. Take some time in front of the mirror to see how things are hanging on you. It’s also worth experimenting with new fits you haven’t yet embraced. If you wear jeans regularly, you might feel comfortable in bootcut denim. However, don’t be afraid of seeing how a new pair of slim fit jeans or a tapered leg work for your body type.
First Date Outfit Ideas: The Basics
Whether you’re thinking about buying an all-new outfit or delving into your wardrobe for inspiration, there are a few key style rules you need to follow. Alongside a flattering fit, color is incredibly important. It’s tempting to make your mark with fiery hues and eye-catching prints, but a neutral palette will always prove the better option. See what you’ve currently got in stock that you can work into your date outfit. Black, gray, and blue are all go-to colors that work well for any occasion. What’s more, they work equally well for casual getups and more formal ensembles alike.
However, if you’re opting for more muted shades, be wary of color blocking. Black and charcoal can be slimming, but there can be too much of a good thing. Instead, add depth by adopting a tonal approach. Use multiple shades of your preferred color to create a standout first date outfit. If you’re looking to break up a darker casual outfit, throw a white t shirt into the mix.
Arrive Fresh and Pressed
This might seem obvious, but you’d be surprised at how many men turn up to a date in clothing that is long-overdue a trip to the laundromat. If you’ve agreed to a casual date, chances are you won’t have to worry about ironing a pair of quality blue jeans or a premium denim jacket. However, if you’re dressing to the nines, preparation is of paramount importance.
If your tailoring hasn’t been out of the garment bag for some time, it may be worth paying a visit to your nearest dry cleaners. A wrinkled shirt is a definite no-go, so spend some time ironing out all those creases. To make your life easier, think about investing in a garment steamer. Handheld steamers are inexpensive and make quick work of ironing tasks.
Accessorize
If you’re taking the tailored route with a first date outfit, there’s no shortage of accessories you can add to your outfit. Ties, tie clips, and cufflinks are all fair game (check out our guide on the Best Shirt and Tie Combinations). However, you don’t want to go overboard. If you want to deploy a full arsenal of accessories, opt for stripped-back designs in muted finishes. Brushed or matt silver is always a good option.
Wearing a watch is also a good idea. These timeless statement pieces have fallen out of favor in recent years since the introduction of smartphones. However, a quality timepiece can really bring an outfit together. They work well with formal outfits, as well as smart casual ensembles.
Finally, consider your underwear options. Even if nobody else ever sees them, wearing some quality briefs or hipster trunks will leave you with a spring in your step. What’s more, if a drinks and dinner date goes well, there’s a chance that underwear is going to be revealed.
Things to Avoid
Some outfitting ideas just don’t work for first dates. Headwear is a definite no-go. Even if you think that designer trilby looks great on you, you’ve got to ask yourself what it’s saying about the kind of person you are. Likewise, sunglasses don’t really have a place in a first date ensemble. If you’re meeting up at the beach in the height of summer, you can keep these kinds of accessories to hand, but don’t build an entire outfit around them.
Don’t Go Too Casual
Agreed to a no-frills casual date? This will broaden your horizons when it comes to picking out an outfit, but don’t get too lazy when selecting your wardrobe. You might get away with a clean pair of designer sneakers if you’re headed off to a daytime date, but it’s best to stick with a nice pair of casual shoes instead. If you’re a fan of denim, keep it simple with a dark wash and leave ripped jeans in the closet.
Just because your casual pieces cost a small fortune, doesn’t mean they’re going to strike the right note with your date. You might have spent upwards of $100 on a graphic tee from a top-tier brand, but all your date is going to see is an uninspired crewneck. Simple casual staples can work well as part of a larger outfit but ditch vibrant prints and logo tees.
Don’t Suit Up
There’s rarely any call for a formal suit on a first date. You might look amazing in three-piece tailoring, but if you’re touching base with someone for the first time, you’ll want to scale things back. Aside from coming across like a tryhard, turning up in a three-piece suit might make your date feel awkward and uncomfortable. If you’re heading to a date from an office job where suits are the standard, consider ditching the blazer and losing the tie for a more laid-back and approachable look.
Classic First Date Outfit Ideas for Guys
Now we’ve brushed up on the basics, it’s time to explore some go-to outfitting options. No matter what you’ve got planned or where you’re looking to meet, these winning combos should see you right, every time.
Daytime Date Outfit Ideas
If you’ve been chatting to someone online and have finally agreed to meet up in person, a casual day date is probably on the cards. These kinds of dates are usually free and easy, with no real venue or structure. As such, you’ll need to dress for the occasion. Ideally, you should aim to keep it casual, although you’ll want to think carefully when selecting your wardrobe staples.
A classic polo shirt or timeless tee works well here. Avoid prints and graphics and reach for solid colors instead. White and gray always work well, but don’t be afraid to add a splash of color into the mix. When it comes to pants, there’s no need to make life difficult. Some quality jeans will always be welcome, so see what dark or light wash denim you have in stock. Chinos are also something to think about. However, avoid anything too baggy. Instead, reach for structured pants with a fit that flatters your waist and height.
You have a few footwear options for this kind of outfit. Sneakers can work if the date is casual enough, but it’s always best to play it safe with boots. If you’re wearing slim fit or skin tight denim, a quality pair of leather Chelsea boots will round off your look perfectly.
Before heading out the door, consider the weather. If fall is approaching or there’s a chance of rain, you’ll need to take some outerwear along with you. Obviously, you don’t want to arrive at your date bundled up in a raincoat. If you’ve got a lightweight parka to hand, wear this. Alternatively, a tailored bomber jacket will keep you warm if your date carries on into the evening.
What to Wear When You’re Meeting for Drinks
Meeting for drinks at the bar? Although this kind of first date tends to be fairly casual, you’ll need to up your game to make a good first impression. As with daytime dates, quality denim is your best friend. However, think carefully about the fit here. You’ll want something comfortable, but roomy fits like straight leg and bootcut should be avoided. Instead, see what tapered jeans you have in your repertoire. If you can’t find anything suitable in your denim collection, chinos can also work well. Just make sure you go with a darker shade.
There are no hard and fast rules on what kind of shirt you should be wearing. A crisp tee can work well with fitted jeans, but you’ll want something that clings well to your shape. Polo shirts are also good shouts. Again, the fit is everything. To dial things up a notch, consider a long-sleeved polo. Dark colors are usually best for evening dates and bar meets. Black and gray are the go-to hues for people wary of too much color. However, don’t be afraid to embrace purple, teal, and mustard shades.
As far as footwear is concerned, stick to casual shoes and boots. If you’re going down the boot route, a classic Chelsea style is always a safe bet. Finally, put the finishing touch to your look with a nice watch.
Casual Outfit Ideas for Coffee Dates
Coffee dates are more popular than ever. There’s less expectation attached to this kind of date, making them more comfortable for both parties. However, you’ll also need a low-key outfit that’s perfect for the occasion.
This type of date tends to be short in length. It might be a last-minute arrangement or a quick meeting that can be slotted into a busy schedule. However, this doesn’t mean you should skimp on your style choices. There might be less time for things to go wrong, but you’ve only got a short window to make a solid first impression with your date.
Casual is the way to go here, although the snappy dresser shouldn’t be afraid of adding sharper garments into the mix. Denim and chinos are easy choices for a coffee date. However, if you’re out to impress, ensure you’re wearing a fit that shows you in your best light. There’s really no call for a button up shirt or tailoring here, so stick to classic tees or polos. Go with neutral colors if possible, but don’t limit yourself to monochrome. Sage greens, corals, and earthy tones can all be effective choices.
You don’t have to worry too much about first-rate footwear when dressing for this type of date. Boots and casual shoes can be worn with confidence, but there’s also nothing stopping you from slipping on a great pair of sneakers. That being said, leave those battered hi-tops at home. A crisp pair of white sneakers will always work well with a casual outfit, especially if you’ve pulled on some dark wash denim.
How to Dress for Dinner
If you’ve agreed on a restaurant venue for a first date, you’ll need to put a lot more thought into what you’re going to wear. Thankfully, you don’t need to go too formal when dressing for a dinner date.
Slipping into a suit might seem like a good idea, but unless the restaurant you’re heading to has a strict dress code, don’t go there. Instead, find a balance between smart casual and something more formal.
For relaxed dinner dates, a premium pair of chinos will go down well. However, it’s worth upping your game with a pair of tailored trousers. A stretch twill fabric is the way to go here, while you’ll also want to consider the fit.
Once you’ve settled on pants, focus on finding the perfect shirt. A dress shirt is the standard for a dinner date. Avoid anything with contrasting cuffs and collars and stick to a neutral shade instead. Keep things simple with a shirt slightly lighter than your pants, or mix things up with more dramatic contrast.
A restaurant venue will almost always expect male customers to wear dress shoes. More laid-back eateries won’t have a problem with Chelsea boots, but it’s probably best to slip into a polished pair of brogues.
Accessories really round out this look, so ensure you’re reaching for your best pieces. A stylish belt is a must. If you want to add a little texture to your ensemble, choose a braided leather one. Finally, think about watches. A chronograph timepiece will go down a storm.
Making the Right First Impression
Dressing to impress isn’t exactly rocket science. However, making the right impression is crucial when it comes to first dates. Before you reach for go-to pieces, consider the type of date you’re heading out to. The venue and time of day will give you a clear idea of what’s acceptable and what isn’t.
If you’ve neglected your wardrobe staples for many years, now’s the time to invest in some basics that will elevate your style game, and of course remember to keep that perfect skincare routine. Make sure you’re wearing clothes that actually fit you and flatter your body. If your clothing collection is lacking in color, now’s the time to spice things up with a palette of neutrals. Finally, don’t forget about grooming best practices. You might have selected a killer outfit, but unkempt beards and hair can ruin all of your hard work. If you need a trim, make sure you schedule an appointment with the barber before your next date.
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