Deciding how to dress for a date?

To answer some of the most common dating questions, we sat down with The Setup’s style gurus: Genevieve Gresset, Heather Drury, and Jesse Turner. Here’s what they had to say about the power of dressing to impress.

Why is it important to dress well on a date?

Genevieve: You only get one chance to make a good first impression. On a first date, it’s important to make that one count!

Heather: Whether we realize it or not, our clothes can express things like our personality or background. Also, it’s usually one of the first things that someone notices about you.

Jesse: How you dress says a lot about you. It’s an unspoken form of communication.

Does attitude matter?

Jesse: Absolutely. Confidence is key!

Genevieve: Whatever you’re feeling in your clothes–it’s going to show. If you wore too little, you’ll feel cold. If you put on too many layers, you’ll get too hot. Maybe your date won’t notice your shivers or sweat, but these things will make you appear uncomfortable. Probably, your date will pick up on that.

Heather: It’s so important to be in the right headspace before going out on a date. Do what you need to do to get in a happy, flirtatious, and playful mood. For my female clients, I always suggest taking a moment to themselves before going out. If you can, try not to go on a date straight from work. First, go home, relax, and get in the right mood. Before a date, take a bubble bath, blast some pop music, and dance around in your room! These are fun, easy ways to help you relax and slip back into your femininity after a long day at the office.

How can I show off my personality through my clothing?

Genevieve: I have one female client who is absolutely amazing. She is a successful, independent, and strong woman with a vibrant personality. To prepare for her upcoming date, sent me five outfit options to choose from. Her friend suggested she go in the baby blue dress with a sweetheart neckline. Although she looked great in that outfit, it didn’t show off her character! I told her to go with the bolder choice–a dress exploding in bright reds and purples. This dress not only flattered her figure but honored her powerful personality as well.

Heather: I think color can be a powerful tool to express your personality without compromising your look. There’s no problem in sticking to a classic silhouette and experimenting with color.

Jesse: Your style should reflect who you are as a person. If you’re a happy, fun, person, that should be reflected in your clothing. The concept of “dressing your best” isn’t about being someone you’re not. It’s about putting your best foot forward so that you can get a second date.

What are the most common fashion mistakes you see clients make?

Genevieve: Women who are self-conscious of their size dress have a tendency to dress in all black. I’m guilty of this, too. We all have “fat” days sometimes! But, when you’re meeting someone for the first time, dressing in all black makes you look like you’re going to a funeral–not on a date.

Jesse: For some reason, a lot of my male clients love wearing socks and sandals. Men, please don’t do this! This combination instantly kills all sex appeal.

Is there such a thing as dressing appropriately for one’s age?

Jesse: Yes. There are some looks that a twenty-year-old can get away with that someone pushing 50 might want to avoid. It’s all about the context and the occasion.

Genevieve: I agree, but it’s important to dress not only for your age but for your energy as well. I recently signed up for a personal styling service called Stitch Fix. I told my stylist that I didn’t want to dress like a typical woman of my age. I wanted something mindful of my age, yes, but also my energy and lifestyle. The box she sent me was full of fun, playful, pieces that showed off my personality while still being age-appropriate.

What’s your most controversial fashion opinion?

Jesse: Hats are no go. I have one client who insists on wearing a fisherman’s cap on all his dates. After his dates, I’ll check in with his matches and ask how it went. They usually say he was nice. But, without fail, they all ask me if he is bald! This man has a head full of hair but because he was wearing the hat, that’s all his dates could think about.

Heather: And if a guy really is bald?

Jesse: Then be bald! Embrace it. Don’t try to hide it with a hat.

Genevieve: I suppose my most controversial opinion is that I actually like hats. I went on one date last summer where both of us wore hats. It made it all feel victorian and elegant. His hat was very cool!

Heather: Hats are one of those accessories where it depends on the context and situation. If you have a sense of style and you’re going for an outdoor date, then there’s no problem with donning a nice sun hat. But, if you’re sitting down at a restaurant indoors, it should be removed. It’s respectable and makes it easier to connect with your date.

What is your favorite fashion hack?

Genevieve: When it comes to dressing for a date, the best hack is to have your outfits ready to go. I tell my clients to have their go-to date looks on standby. That way, when a date comes up, you don’t have to worry about what you’re going to wear. It’s also a good idea to try on those outfits regularly. Make sure they still fit and look good on you.

Heather: Don’t get caught up following trends! Instead, focus on your individual features and stick to what works. Think about what parts of your body you feel most confident about. Try to pick clothing that highlights that part of your body and go from there. Once you figure out what clothing best compliments you and your and features, shopping becomes much easier.

Jesse: Before you go out, look in the mirror and ask yourself: “How approachable do I look in this outfit?” or “What does this outfit say about me?” If you want to make a great first impression on your date, thinking critically about your clothing is a good first step.

How do you help your clients to get out of their fashion comfort zone?

Genevieve: Wear it at home! Take pictures of yourself to see how you look from different angles. Maybe you like a certain outfit, but need some time getting used to it. That’s when you can wear it out for a night out with friends. Never use the first date to try out an outfit you’ve never worn before. Take it for a test run with friends or at home so that you get used to how you feel in it.

Jesse: I’ve always been slim. So, growing up, people would always comment on my size by telling me to eat a burger or something like that. thinking that it would disguise my frame, I started wearing baggy clothes. At the time, that type of clothing felt like a shield protecting me from other people’s judgments. Later in life, I switched up my style and started wearing tailored shirts and pants that actually fit. Now, I get compliments all the time on my style. I am more confident now that I’ve embraced my authentic self and started dressing in a way that actually compliments my figure–not hides it. So, I tell this to clients if I sense they need an extra push. Once you make that change, you’ll never regret it.

Heather: Just try it on! You don’t have to buy it. And if you do buy it, you don’t have to wear it. Just like meeting new people, you’ll just never know until you try.

I’m still learning the fashion basics. At what point can I trust my own sense of style?

Jesse: I think when you start to notice other people complimenting your style, that’s when you can feel confident in your choices. This is not to say that you should rely on the validation of others, but it is a good point of reference.

Genevieve: Your first inclination might be to seek the opinion of others. But, family and friends aren’t always trustworthy in these things. If they think something looks bad on you, they might find it hard to tell you the truth. As matchmakers, we have no problem being brutally honest. That’s what we’re here to do! So, take advantage of us as a resource. Send us photos and we will give you honest feedback.

Heather: The more you try something new, the more it becomes a part of who you are. If you ever feel insecure about a look, we are here to help.