Whether you have been together a long time or it’s your first date, deciding what to wear for a dinner date is both fun and nerve-wracking! After all, first impressions count, and even if it’s not your first date, what you wear, and how it makes you feel sets the tone for the evening.
There is a lot to consider—is the date casual or formal? Are you doing more than one thing- for example, playing tennis, then going out for dinner? Do you have to pack your date clothes to change at work or do you have the luxury of spending the day pampering before going out?
Clearly these factors, as well as your level of interest in your date, your sense of style, and your own code of dating conduct come into play—and make a difference as to what you choose to wear. I am a formal person—I love fine dining and getting dressed up, but a spur-of-the-moment casual bite to eat can be fun too. I tend to like to be “overdressed” rather than “underdressed” but that’s just me. Knowing your own style, the kind of activities you like, and feeling comfortable go a long way toward a successful date—whether you decide you like the person or not. I am one of those people who believe you can have an interesting date even if you decide the person isn’t right for you long term, or that they are going to be a fun friend rather than a romantic partner. It’s usually interesting to meet new people and to try new things. However, we’ve all had an insufferable date or two.
People are pretty casual these days, especially here in Florida, but it’s important to make an effort when someone has asked us out—they are putting forth their time and resources forward, and you have accepted their invitation, after all. I saw a survey on men’s reactions to their recent first dates—one of the main complaints the men had was that it didn’t appear that the woman had made an effort to dress well for a dinner date. Ripped jeans, cut-off shorts, and athletic attire were cited as common inappropriate date outfits according to the survey respondents. These looks may be great for a casual day running errands or working out at the gym—but they are not for a nice restaurant, nor for a first date. I get it–sometimes we want to feel comfortable, but elevating your look will go a long way to create a good first impression.
Anyhoo, I thought I’d style a few looks for various types of dates as inspiration. You can shop your closet, adapt my suggestions to your personal style, or shop a look right from this post. I’d love to hear about a great date and what you wore in the comments below.
What to Wear on A Coffee Date:
St. Barth Maxi Dress
Boho Floral Romper
Tie Front Short Sleeve Maxi.
Ever the cautious type, if I don’t know a prospective date well, I will often suggest a coffee date. I like to set it up so I have somewhere to go afterward so there is a specific ending time in case the date doesn’t go well. If it does, we have something to look forward to the next time we get together.
A coffee date doesn’t usually involve drinking alcohol so everyone’s judgment is more clear, it’s a little more casual so people tend to be more relaxed —unless you drink too much coffee—and you can at least figure out if you want to get to know the person further.
Casual chic is my go-to daytime look, a pair of jeans, a nice top, a cute handbag, and a pair of great sunglasses set the stage for the perfect coffee date outfit. A casual dress is also a great choice for a chic look, also.
First Date:
The purpose of early dating is to get to know the person you are going out with and to decide if you’d like to get to know them more. Because of this, I prefer not to dress suggestively. Once I have decided I am interested, I go for something a little more revealing. I am old-fashioned—I think physical intimacy should come much later in the relationship—once you know the person and are interested in a committed relationship. I know that people aren’t always interested in going for a committed relationship, and if you aren’t, then, by all means, find something sexy in your closet and go for it.
I like to know where we are going so I can choose an outfit that is appropriate to the place and I like to get a peek at the menu as well. Often the vibe of the restaurant or its location serves as outfit inspiration. In addition, I want to know whether we will eat indoors or outdoors as well. I always bring a wrap or sweater in case the restaurant is cold, or if the evening is chilly.
Farm Rio Graphic Midi
Ungaro Wide Leg Pant
Teagan Dres
First Date Formal:
While many first dates are casual, it’s always nice when your date invites you to a formal first date—even though choosing the right outfit may seem daunting. If you don’t have a lot of formal clothes, a little black dress is a great addition to your wardrobe. If you choose a classic style, a little black dress can serve you for years to come and can be styled in many ways.
It’s always fun to get something fresh and new if you can—and I’m definitely here for you with a few great looks. Here are a few suggestions:
First Date Casual:
I knew a wealthy guy who always took his first date somewhere casual. If the date went well, he would take her to more formal and expensive dates. This was partly because he wanted a partner who enjoyed the simpler things as well as life’s luxuries, and he also liked people who were flexible and fun-loving. Ball games, fairs, and picnics were among his choices for a first date.
While jeans are always an option, it might be fun to wear a dress and throw on a leather jacket or elevate your jeans outfit by adding a cute top, high heels, and a long coat or a trench coat. Adding a “third piece” elevates a great casual outfit. If you go for the ripped jeans look, adding a formal blazer and a pair of heels is a great way to balance this type of casual jeans. I would avoid athletic wear unless the date includes a sports activity.
Dinner Date
Dinner is a lovely way to get to know someone new or to spend quality time with your significant other. Clearly, the restaurant your date chooses plays a part in choosing the right outfit to wear. In addition, the weather and time of year also play a part in what you might wear.
In the summer, I’d jump on the romantic trend, and chose a cute dress, either a bodycon dress with a jacket or sweater or something floaty and romantic. A pair of linen wide-leg trousers with a romantic top is also a good look.
For winter weather, I love styling leather pants with a chunky sweater or a chic blazer. High boots and a beautiful knit dress are always a good choice for a first date outfit. This is a great office to evening outfit.
Daytime Date:
Daytime dates can be lots of fun—and usually entail attending an event, playing a sport, enjoying a picnic or hanging out at a resort. Clearly, daytime date outfits are heavily dependent on what you are going to be doing. Dressing for whatever activity you will be doing will help you have a good time. You want to be comfortable, yet achieve the right balance between being comfortable and looking good. In the summer months, you might wear a cute dress, white sneakers, and a cozy sweater or denim jacket over your shoulders. Finish with simple accessories and you have the perfect casual first date daytime outfit.
After work dinner date:
While many of us now work from home, some are back in the office. In this instance, I would wear a nice sweater dress to work with a pair of boots and a scarf. For dinner, I’d swap out the boots for strappy heels, and a beautiful string of pearls. I’d tuck an evening bag into my work tote, so a whole evening look comes together with ease, and of course, such a chic outfit will definitely lead to a second date.
Swapping out the pants from a pants suit for a pair of faux leather pants, or swapping in a sequin top or lacy camisole is a great way to change a pants suit from day to evening. Best of all, the few pieces you need can fit in your tote.
Dressing for A Special Occasion:
Sometimes a first date is also a special occasion, such as a company Christmas party, or a wedding. I think it’s pretty adventurous for a guy to invite someone he doesn’t know to a special event, but it definitely happens. Naturally, we want to make sure we have dressed appropriately. One of my girlfriends dressed in costume for a special occasion date. It turned out to be a huge mistake, and she was mortified. They did end up getting married though–so you never know.
A little black dress, or black pants and an elegant top are always good to have on hand. I collect beautiful tops I can pair with black pants or a skirt so I can put together something interesting from my closet. Having a few wraps, and some pretty jewelry to elevate a simple dress is always a good idea.
If you are a fashion lover, you might go for something a little more interesting–here are a few ideas:
What to Wear to a Movie Date:
Movie theaters are notoriously cold, so I always wear or bring a sweater or jacket. I wear, leather pants or nice trousers.
Casual Dinner Date:
Pretty sundresses, casual dresses, leather trousers for winter, white linen for summer, and of course jeans all make for great outfits to wear to a casual dinner date.
The Best Dinner Date Outfit:
The best dinner date outfit is one that suits you, is appropriate for the restaurant, is comfortable, and makes you feel confident and amazing. The more confident you feel, the better the date—whether you are going on a first date or you’ve known each other for thirty years or more.
Date Night Outfits for Women Over 50:
I am often asked to share specific outfits for women over 50. The truth is that good taste is ageless. I would give the same advice to women of any age—make sure the clothing you choose suits you, fits you properly, is clean and in good repair, and finally is appropriate for the activity you are doing.
If you have body concerns
Here are a few strategies to consider…
- Cover it. I often hear that women don’t like their arms, neck, or legs—which is sad. It is, however, easy to find long sleeves, scarves, turtle necklines, longer hemlines, or pants.
- Camouflage it. Look for tailoring that helps reshape your physique, details that draw the eye away from what you don’t like such as rushing, or details that confuse the eye, such as the creative use of animal or floral prints.
- Column dressing (like the look on the left) is another great way to create a streamlined silhouette.
- Play up a feature you do like and ignore the things you don’t like. That’s what I do.
A little Etiquette
Who should pay for the date:
The question of who should pay for the date comes up shockingly often. It’s interesting that the topic of who should pay comes up when it seems so obvious but I had a few dates back in the day who suggested we go “dutch treat” as the bill was dropped off. Luckily, I had the money to cover my meal but I never went out with them again.
The person who does the inviting is the one who pays. If he or she has indicated upfront i.e. when they extend the invitation, that the date will be “dutch” which means that each person pays for themselves, then you can decide whether you still want to go out with them and whether you have the money to go. In addition, if a man asks you out but “forgets his wallet” this is a huge gaffe and red flag.
Tardiness:
If he or she is late: If he calls and says he is going to be fifteen or twenty minutes late, unless there is a time issue–such as reservations–I would go forward with the date. If he is going to be considerably longer, I suggest rescheduling. If he doesn’t call, in my book, the date is canceled–permanently.
We teach people how to treat us and if we allow tardiness, rudeness, or poor manners, we are letting the other person know that we will give them latitude. It has been my experience that this leads to their taking more and more latitude with the relationship leading to disrespect and increasingly untenable behavior.
The “booty call” if you don’t want to be the booty call, “No” is the simple answer. “No, you can’t come over right now–but I am available next Wednesday directly after work.” or whatever actually works for you. If he can’t accommodate getting together for dates with you, and only wants sex–it’s not a good fit unless that’s what you want too. Once a low bar has been set, it’s very difficult to change it.
The Relationship Isn’t Developing:
There is this book called “He’s Not That Into You.” It is the perfect response to all those questions we have like, Why hasn’t he called? Why does he just take me out randomly? Why hasn’t he introduced me to his family? Why is he always late?
Why doesn’t he ever take me out?
When he just stops by around 10:00 p.m. or later, it’s called a booty call. This means that he is only interested in having sex but not interested in dating or having more than a sexual relationship with you.
If you don’t want to be the booty call, you can simply say no. “No, you can’t come over right now–but I am available next Wednesday directly after work.” “Sorry, I need my sleep right now–but we can get drinks on Friday.” If he can’t accommodate getting together with you under terms that work for both of you, and you don’t want to be the booty call, the guy simply isn’t that into you. If you want something different, you will have to set higher standards and look for someone else who meets those standards.
The Second Date:
Just as you are considering whether you are interested in having a second date, he (or she) is too. Sometimes a second date just isn’t in the cards for all sorts of reasons. We may wonder what went wrong—did we say or do something? We shouldn’t look at it that way. Each of us is entitled to like who we like and if your date isn’t interested in going further, he or she deserves to make that decision just as you have the same option. It’s far better to know the truth than to
I never push relationships, I think it’s always better when people naturally develop a relationship and allow it to go at a comfortable pace. If your date is not calling you back, consider it a sign that he or she is not that interested. When people want a relationship, they naturally pursue it.
