Best Shoes to Pair with a First Date Outfit Reviewed
There’s no denying it - going on a first date can be a pretty nerve-wracking experience. Other than worrying about how the date itself is going to go, you also need to pay special attention to your appearance. You don’t want to go overboard - unless it’s a formal occasion - and maybe you want to thread the needle between that natural, effortless look, but not so effortless that it looks like you haven’t put in any effort at all. It’s complicated.
Since the term ‘first date outfit’ is a broad one, we decided to put together a list of a variety of shoes that may be suitable for the occasion. We hope that you will find what you like - and what you need - without any problems! Good luck!
This is the best product on our list that is currently in stock:
Genuine Leather Upper
Adjustable Buckle Closure
N5 Comfort+ Technology
Chunky and Elegant
1. Nine West Starship
Genuine Leather Upper
Visually Slimming D’Orsay
Elegant and Chic
Different Color Combinations
Needs Breaking In
In terms of the design shape, you can’t go wrong with a d’Orsay look. With the sides of the shoe cut away, the visual effect is one of longer, slimmer legs, and a more elegant figure. The Nine West Starship is a great example of simplicity made graceful, a flat that will work just as well in an office setting as it will with a first date outfit.
The Starship is made from genuine leather for the upper. The leather will conform to your feet over time, providing you with a personalized type of comfort. It has a pointy toe for a sharp, dashing finish, and a micro heel in the back. It comes in several different color and finish combinations, from smooth to plush leather, to cork, to a leopard print, and you are definitely going to find one that suits your personal tastes!
The Nine West Starship is a versatile choice that will find its purpose over and over again even after your first date is long over. It goes well with boyfriend jeans and a French-tuck shirt, as well as with a pencil skirt and a silky button-up for office glam. There is truly nothing the Starship can’t pull off!
2. Naturalizer Julisa
Genuine Leather Upper
Adjustable Buckle Closure
N5 Comfort+ Technology
Chunky and Elegant
Heel High for Some
We talk a lot about simplicity and the need for being neutral in this guide, but in case you want that pop of color and a higher heel - in case you’re feeling bright and bold for your first date - the Naturalizer Julisa will be a perfect fit. This high heel strappy sandal is a great option both for a day outing, and for a fancier dinner date, and it will wow you with its comfort technologies!
The Julisa’s strappy upper is made from genuine leather. The strap across the ankle has a buckle closure and is adjustable for that perfect width. The shoe is outfitted with the N5 Contour+ technology for comfort, meaning that it comes with dual density cushioning, a heel cup to keep you well-balanced and stable, as well as molded arch support for maximum wearability. The square toe and the blocky, 3.5-inch heel of the pump will bring you back a few decades in fashion, to when life was more disco and more carefree.
You can also feel carefree in the Naturalizer Julisa! There isn’t anything we don’t love about this pump - from its warm color to the strappy upper which you can dress up or dress down, to the insane comfort it comes with - if you’re looking for a heeled option for your summer first date outfit, you can’t go wrong with the Julisa!
3. Cole Haan GrandPro Tennis
Genuine Leather Upper
Reduces Foot Fatigue
Casual Yet Fancy
Not Enough Support
Tight Toe Box
Cole Haan is a company with 90 years of experience in crafting only the most elegant, most impeccably made shoes. They put emphasis on the quality of their materials and the comfort of their construction, and there is hardly a design which won’t take your breath away. The same is true for the GrandPro Tennis sneaker. If you are looking for something casual and comfortable, but still elevated for your first date outfit - not your average sporty look - then this shoe is a great option.
The GrandPro Tennis comes with a genuine leather upper in a variety of colors, out of which we have singled out this metallic one as a stand-out piece. It has a rubber sole for durability and slip-resistance, and Cole Haan patented Grand.OS comfort technology.
Grand.OS is grounded in the principles of flexibility, responsive cushioning and unbelievable lightness. Shoes with this technology move with your foot and provide energy return on every step, which helps reduce foot fatigue after a long day of walking.
In terms of casual and yet fashionable shoes, we can’t think of a better choice than the Cole Haan GrandPro Tennis. It is lightweight, supportive and flexible, and it will feel like an absolute dream as you focus on your first date and stop worrying about your feet.
4. Clarks Verona Trish
Simple Leather Upper
Zipper in the Side
Comfort Soft Technology
Comfy All-Day Wear Heel
The pinnacle of autumn style, the bootie that everyone needs in their wardrobe come chillier weather - the Verona Trish from Clarks is a simple, easy choice to make when you’re deciding on a first date outfit for fall. It is a design that will take you from day to night without problems, made from premium leather and with a heel to provide just enough boost to make you feel irresistible.
The Verona Trish comes in a few color options, from classic black to tan to this taupe in our picture. It has a zipper in the inner side for easy on/off, and a round toe for comfort. It is also outfitted with the Cushion Soft technology, layers of foam sitting underfoot for maximum support with each step. The heel of this bootie is barely 3 inches high, meaning you can easily wear it for however long you want to!
The Clarks Verona Trish is a must-have. A bootie that goes well with jeans and leggings as well as skirts, and which you will wear for seasons to come, not just for the first date you have in your schedule. It is made of quality materials, equipped with all the latest innovations to make you as comfortable as possible, and it will make a great addition to your wardrobe.
5. Toms Beverly
Genuine Leather Upper
Two Inch Chunky Heel
Soft Microfiber Lining
Cute and Casual
Not for Wide Feet
While we usually associate Toms with those ubiquitous slip-on summer designs, which have a cloud-like footbed and a breezy upper, today we’re here with something a little different. The Beverly pump is a little more put together, a little more sassy, but no less comfortable than the brand’s iconic slip-on sneaker. It will be a perfectly cute finishing touch on your first date outfit!
The Beverly has a round-toe silhouette that is easy on the toes, and a full-grain leather upper that takes on the shape of your foot over time, providing you with a whole other level of comfort.
The inside of this pump is lined with soft microfiber that is gentle on the skin and won’t leave you with any blisters or abrasions. Toms goes out of its way to ensure the utmost comfort in this heel, as it comes with an Ortholite insole - this provides cushioning and energy rebound to take the stress off of your joints. The heel of the Beverly is made out of wood, with an oak finish, a square shape, and almost two inches in height, which makes it perfect for walking around all day.
The Beverly is that classic casual pump which you need in your wardrobe for when you don’t want to be too fancy, but still want to leave your sneakers at home. It is comfortable, versatile, and it will make you smile as you greet your date for an unforgettable time.
6. Steve Madden Irenee
Genuine Leather Straps
Genuine Cork Footbed
Adjustable Buckle Closure
Romantic Metallic Shimmer
Needs Breaking In
Strap Breaks Easily
Doesn’t the pink metallic shimmer of this lovely sandal just make you smile? The Irenee from Steve Madden is wonderfully romantic and feminine in its design, not only because of the color but also because of its dainty straps and elegant silhouette. It is a sandal with an upper made out of genuine leather - the straps won’t cut into your skin or hurt you in any way. Around the ankle, there is an adjustable buckle closure which you can customize to your liking, and this gorgeous sandal accommodates ankles of all widths.
The footbed of the Irenee is a special treat - it is made out of genuine cork. Cork footbeds provide tailored comfort since they mold to the shape of the foot, and provide ample impact resistance. Moreover, cork is great at odor control. This is a moisture-wicking material that allows your feet to breathe and prevents unpleasant smells.
The heel of the Irenee is ideal for a first date outfit - it is not too tall with its almost two and a half inches in height, and it is remarkably stable thanks to its blocky shape. In this sandal, your steps will be confident and well-balanced.
Honestly, it is difficult to find a fault with the Irenee. If the weather is nice outside and if you are not shy about showing off your toes or adding some elevation to your height - definitely go for these minimalist sandals!
7. Converse Chuck Taylor
Breathable Canvas Upper
Rubber Toe Guard
Countless Color Options
Not Very Durable
Not for Wide Feet
The one, the only, the legendary - the Converse Chuck Taylor. A design which has remained largely unchanged in over 90 years since its initial release, it first started out as a basketball shoe, before being adopted by pretty much everyone - from the cool kids to the computer nerds, from musicians and artists to weightlifters - there is hardly a place where you won’t find the iconic Chuck Taylor.
And so it somehow winds up in this guide as well. We have turned to this classic silhouette as a great option for those dates where you’re not sure where you’re going, and you’re not sure what you’re wearing, but you want to be comfortable and carefree at the same time.
The Chuck Taylor is an amazingly lightweight sneaker. It has a thin, breathable upper made out of canvas, which comes in an astounding number of color combinations. Of course, this design was made easily recognizable by its rubber toe guard, as well as the rubber sidewall around the sneaker, with colored stripes.
It doesn’t lack flexibility nor slip-resistance, as the rubber outsole of the Chuck Taylor comes with a special pattern that makes sure you stay on your feet regardless of the surface you’re on.
Chuck Taylors have permeated every area of the fashion world, and thus today you can pair them up with jeans, shorts, skirts, dresses, and even suits to achieve that cool, rebellious vibe no matter where you go.
8. Sorel Farah
Waterproof Suede Upper
Adjustable Tassel Detail
Die-Cut Memory Footbed
One and a Half Inch Heel
Tassels Too Long
Not for Wide Feet
Logically speaking, we can’t all have our first dates when it is warm and summery outside. What happens when the days are cold? When it is raining or snowing and we still need to look our best? There’s quite a simple solution for that - ankle boots! A design such as the Sorel Farah, which will keep your feet dry and warm while putting that chic twist in your outfit is a perfect choice.
The Farah is constructed out of rich, super-supple suede that is waterproof and able to withstand anything from light rain to light snow. There is a playful tassel detail around the shaft of the bootie which adds some interest to the design but also serves to provide the right fit. Adjust the length and the tightness of the tassel straps however you want, as the boot fits all ankle sizes!
On the inside, the Farah provides cushioned support thanks to its die-cut memory footbed, and a molded rubber insole. These take on the contours of your foot and make sure that you are comfortable no matter how long you spend on your feet.
Finally, there is a leather-wrapped heel of about one and a half inches in height, which is sturdy and stable, providing you with a good base to walk on.
The Sorel Farah is a versatile bootie which you will have fun wearing with tights, skinny jeans, and even with that chic wool skirt you just bought. It will keep you warm and protect you from wet conditions, and really, what more could one possibly ask for?
9. Sam Edelman Felicia
Kid Suede Upper
Roomy Toe Box
Dozens of Color Choices
We understand that this might seem to be a simple, uninspiring ballet flat at first glance, but hear us out. A design such as the Sam Edelman Felicia, made out of high-quality suede materials, lined with leather and with a padded footbed, transcends fashion trends. This timeless, iconic round-toe silhouette will never go out of style, no matter what the fashion climate is like.
The Felicia is a ballet flat with nothing short of addictive comfort. The secret is in the kid suede upper, which is soft and gentle on your skin, not causing any chaffing or blisters. Suede has that wonderful ability to conform to the shape of your foot over time, and so the more you wear it, the more Felicia will feel like a second skin on your feet.
The leather lining in the Felicia is also there to promote a healthy foot environment. Thanks to its breathability, leather allows air to circulate in and out of the design, preventing bad odors, as well as any infections that might arise from spending too much time in confining footwear.
Additionally, there is 4mm of padding in the insole, which provides you with that cushioned comfort required for all-day wear.
As most flats of its type, the Felicia is amazingly versatile. It will work well with any outfit, be it skinny jeans and a cool jacket, a maxi dress or a flowy floral skirt. Everyone needs a pair of all-purpose flats like these to complete their collection, and the Felicia will definitely not let you down!
10. Calvin Klein Gayle
Premium Leather Upper
Gel Pod Inserts
Three Inch Heel
Everyone needs a simple, neutral pump in their closet. These sophisticated, sleek shoes are appropriate to wear in absolutely any situation - from a casual lunch meeting to an office party to even a wedding reception - and they look amazing on all body types. The Calvin Klein Gayle comes from a renowned fashion designer who is a master of minimalism, and who delivers a modern, uniquely refined aesthetic.
This pump has that classic three-inch stiletto heel which will take you from day to night without even a hint of pain. It is flexible and supportive with its signature gel pod inserts, which are essential when you’re walking in high heels. The extra cushioning helps distribute your weight more evenly inside the pump and takes the strain off of your ankle, knee, and hip.
Furthermore, the Gayle has a slip-resistant and weatherproof outsole which reduces the risk of stumbling and injury, while at the same time providing you with necessary shock absorption. We have yet to see a high heel design which is this comfortable to wear.
Lastly, the premium leather this pump is constructed of provides luxurious comfort, and it is available in an array of seasonal colors.
For when you need to look your best but still don’t want to go all out there, the Gayle is the perfect compromise. It will keep you cushioned and comfortable, and you will definitely not regret treating yourself to this timeless design.
Criteria Used for Evaluation
When we’re choosing the right shoes for any occasion, the first thing we think about is the style. (Except maybe in the case of sports sneakers, hiking boots and similar, when functionality might be more of a priority.)
Now, while we do want you to be yourself on your first date, we have to mention how it is also important not to overdo it. This occasion is all about getting to know the other person - and them getting to know you - and too many accessories, clashing prints or even layers may send the wrong message.
We could divide all of the designs in our list into casual ones, such as sneakers (the Chuck Taylor, the Cole Haan GrandPro Tennis) and ankle boots (the Clarks Verona Trish, the Sorel Farah), and those which are fancier, such as pumps (the Calvin Klein Gayle, the Naturalizer Julisa).
Casual is always a good option for when you’re not sure where you’re going or are going to a more lowkey place. Sneakers, ballet flats and round-toe pumps with chunky heels are great to wear with jeans, shorts, and casual skirts, for a more laid-back, relaxed vibe.
If your first date requires you to dress up a little, however, then a pointy-toe pump with a low heel is the right way to go. These have a classic, elegant silhouette that works well with pants and dresses, and you can always accessorize to either take it up a level or bring it down to a more casual elegant combination.
Another thing to consider when you’re thinking about style is the time of the year. If it’s cold outside, perhaps raining or snowing, definitely reach for a cute ankle bootie to keep you both protected and warm. These are flattering for everyone and are a great addition to an autumn outfit, with a camel-colored coat or a snazzy trench.
If, on the other hand, the evening is warm and breezy and your feet need a break from confining shoes, sandals are your friend. Throw on a nice color on your toenails, fasten the ankle strap on your favorite go-to sandal, and enjoy your summer first date.
Really, when it comes to style, the possibilities are endless. As we have mentioned before, each person has their own preferences, their own aesthetic, and even their own comfort levels. If someone loves sneakers and wouldn’t be caught dead in a pair of heels, someone else likes the elevation in height and the confidence that heels bring.
What is most important is that you feel comfortable in your own skin and that you stay true to yourself, and thus you should make your first date choices accordingly.
Other than style, one more thing that is crucial when trying to enjoy your first date is that you’re comfortable. We have already talked about this in relation to being at ease in your own outfit and with how you look, but it is also important in the literal sense of the world.
You want your feet to be cushioned, supported, and you want the upper of your shoes to be gentle on your skin. Abrasions, blisters, hotspots or any type of chafing are simply unacceptable.
Different brands achieve the necessary levels of comfort, support, and stability using different techniques.
Most of them rely on the standard, well-known features: cushioned footbeds that provide shock absorption, minimizing the impact force which travels up to your joints and thus relieving them of added strain; molded footbeds which fit the contours of your foot sole and cradle it as you walk; uppers made of leather, canvas, or any other type of material which easily changes shape over time, and becomes tailored to the form of your foot.
All of these are comfort options which work for the majority of people, and should most likely also work for you.
However, there are also those brands which go a step further and include special technologies in their construction. We have encountered this in the case of the Cole Haan GrandPro Tennis sneaker and the Naturalizer Julisa. These companies have their own advanced features which they have specifically developed with the comfort of their customers in mind.
That is not to say that shoes with comfort technologies are in any way superior to the ones without. As with most things, it is all a matter of preference. An advanced feature may work for one design of a brand, and yet be completely wrong for a different one of the same brand. Similarly, one genuine leather design will not have the same comfort levels as a different genuine leather design.
It comes down to the shape of our feet, the strength of our muscles, and even our pain levels. If you’re able to, it is always a good idea to try on a shoe before you decide to buy it. Walking in a design, for a however short amount of time, can be vastly different than looking at its picture or reading about it online.
If you’re not yet sure what look you’re going for on your first date, then you can’t really know which shoe style to go with, either?
We understand better than most that moods change, as well as the weather - perhaps today it was raining and tomorrow it will be sunny again, or the other way around - and that what we want to wear at any given time depends largely on how we feel.
However, in order to have that right pair of shoes at the ready no matter what outfit you come up with, you need a versatile design. One which looks just as good with a pair of boyfriend jeans and a T-shirt as it would with a chic jumpsuit.
This is why we have ranked the shoes in this guide according to their versatility as well. We looked at their overall designs and rated them according to their suitability for more than just one occasion. After all, you can’t wear open-toed sandals on a cold winter day, just as you can’t wear ankle boots in 90-degree weather.
It is nice to have that go-to option in your closet to throw on and to be confident in your outfit, no matter where you’re going.
There are instances - such as blind dates - where you might not be sure what the other person looks like. If they are taller than you or shorter than you, if they wear flat shoes, or prefer to wear heels themselves.
In terms of heel height, first, think about how skilled you are in wearing high heels. Have you had enough practice in that? Are you positive that you can walk without any wobbly movements or fear of stumbling? Or are you mostly wearing flat shoes these days, and are not one for added height?
In case it is the last one, we advise that you stick to flat shoes on your first date as well. If you are unsteady in high heels, that will only make you focus on how difficult it is to walk in them, and will take away from your ongoing first date. Remember: wear what you’re comfortable in; a cool sneaker or a sassy ballet flat will do the job just fine.
However, if you’re more certain of your high-heel-wearing skills, we have some tips for you.
Let’s start with the shape of the heel: you want to be stable. You want to have a good foundation as you walk, and would prefer to avoid Bambi-like legs. In that case, think chunky heels. Thick, blocky shapes are an excellent base, and they won’t let you lose your balance.
Another solid option is the wedge heel. These are also insanely comfortable, as they evenly distribute your weight across the heel, and take the pressure off of the ball of your foot.
If you’d like to keep your balance, it’s best to stay clear of stilettos.
Next in line is the heel height: while sky-high heels are sexy and undoubtedly will leave an impression, you won’t be able to walk in them for more than a couple of hours. Anything that is four inches or higher is a killer on your feet, which could also be a mood killer on your first date. For a comfortable first date, all-day and all-night wear, choose a lower height. Kitten heels of two inches and classic heels of three inches are perfect options for that.
Lastly, padded footbeds are your friend. We have already talked about the benefits of cushioning in the comfort section, but here we have to reiterate - anything that adds more support to your foot in a high heel is more than welcome. So don’t shy away from cushioned insoles, as they will only help you stay on your feet for longer.
Alternatively, if a design you like doesn’t have extra padding on the inside, you can always invest in a pair of gel inserts and put them in yourself.
The quality of shoes largely depends on the quality of their materials. There is also the factor of construction techniques to take into account as well, but in this section, we will focus primarily on materials.
What we mostly encountered in our research are shoes made out of durable, high-quality materials. These include genuine leather and suede, cork, microfiber, canvas, and rubber for the outsoles.
Genuine leather and suede, in particular, are considered one of the best materials for shoes, mostly because of their durability, breathability, and the ability to mold to the shape of the wearer’s foot. Leather allows air to pass in and out of a design, maintaining a healthy climate within the shoe, and it is also incredibly long-lasting, especially if regularly cleaned and conditioned.
However, if the leather is layered too thinly, as we have seen in the case of the Sam Edelman Felicia, for example, then it gets worn out quickly, and the design doesn’t last longer than a couple of seasons.
When it comes to the durability of a design, to how breathable it is and how comfortable it feels, it is widely known that synthetic materials aren’t as high in quality as natural ones are. Of course, synthetic materials are safe for the environment and completely vegan, but if you want your shoes to be worth the investment, you’ll look for those made out of genuine materials.
Expert Interviews & Opinions
We all get nervous on our first dates. It's a natural human reaction! You want to impress and dazzle this person who has captured your affections. If you're worried about nervousness, try some breathing exercises. You can look up all sorts of tips and tricks for dealing with nervousness and stress online.
The best piece of advice we can give is to just be yourself. You don't want to transform into somebody completely different, because you may not be compatible when you reveal your true personality. The best way to find your soulmate is to always be authentic. After all, you're a wonderful person who deserves real, passionate love. Show that beautiful person you are!
Other Factors to Consider
As you saw in our list, most of the shoes have a neutral color that goes well with everything. This includes white, black, nude, grey, navy, etc. There are also some stand-outs, such as a classic red for elegance, and some metallics for a touch of glam.
Of course, the color of your shoes depends on the overall color of your outfit, and that you certainly won’t opt for something that is not complementary.
However, in the case of a first date, it is advisable to go with a less eye-catching color. It is best to save sparkles, mustard yellows, hot pinks and intense print combinations for some other outing. After all, you want all of the attention on the first date to be on you, not on your feet, right?
Choosing the right outfit for a first date is not easy. We want to be understood and liked, and we want to both have a good time and show someone else a good time, and preferably we would like not to look like a gremlin in the process.
And while we can throw out endless tips and advice, when it comes down to it, it is all about what your aesthetic is. If you’re a jeans and a Converse type of person - don’t change it! If you prefer pencil skirts and d’Orsay flats, then wear that! There is no one universal rule when it comes to dressing for such a broad situation as a first date is.
At the end of the day, you got asked on a date, or someone accepted your invitation because they probably already liked what they saw; there’s no point in stressing over it.
What is important is that you take a deep breath in, and relax. Remember to have fun, to smile and be yourself, and the rest will follow. You got this!
Frequently Asked Questions
q: What if our first date is on a beach?
A first date on a beach is probably the only time we will say that wearing flip-flops is acceptable. Especially if you expect to be walking on sand - choose shoes with flat soles, open toes, and with some water resistance, in case you decide to splash in the shallows.
Alternatively, you can always simply take off your shoes and enjoy the warm sand between your toes on your romantic walk along the beach.
q: Can I wear my sports sneakers on the first date?
If you are a sporty, athletic type of person - you can definitely wear your sneakers on the first date! Of course, it goes without saying that you should bear in mind the place you’re going to - sports sneakers are unacceptable in upscale restaurants, but perfectly fine when taking your pets out for a walk in the park.
q: Do I need to break in my new shoes before the date?
Absolutely! We already emphasized how important it is that nothing distracts you from showing the best side of yourself on the first date, and that includes pinched toes, blisters, lacerations or any other unpleasantries. These can be easily remedied by breaking in your new shoes before the big day.
Make sure to wear your new shoes around the house for at least an hour or two every day, preferably with some thick socks on to get them nice and stretched out so they don’t give you any problems during the date itself.
q: What if I get blisters during the date?
Ouch, getting blisters is never fun! However, if your date is going well, you might ask the other person to sit down with you for a while, to get off your feet for a moment. Think a warm bench in a park, or a cute cafe in the city. You can also always visit the nearest store and get some bandaids to cover the blistered areas. It's not ideal, but it will tide you over until you get home and are able to take off the shoes for good.
q: What if I don't know where our first date is going to be?
There is something inherently romantic in someone else organizing a surprise for you. However, that makes it all the more difficult to choose an outfit for the event. If you're not sure where your first date is going to be, perhaps you could at least ask about the dress code? Whether it's formal, or fancy, or just casual.
If not even that, your best bet would be to go with a safe option. Something cute and casual, but which can easily pass for dressy - or kind of dressy - if the situation calls for it. Ballet flats and a dress, a crisp button-up and jeans and sleek sneakers - these are versatile enough for many different occasions.