WHAT TO WEAR ON A FIRST DINNER DATE: TIPS FROM TAELOR’S FASHION STYLISTS (with checklist below)

How should I dress to impress my dinner date? Good question! Picking out the perfect first date night outfit for a date is tricky. You want to be bold but not too intimidating. Or you want to look friendly but don’t want to be put into the friend zone. You want to stay true to your personal style, but you want an elevated look. Our fashion stylists at Taelor provide date night outfit ideas and helpful advice on how to make the great first impressions on your next date. In men’s clothing, choosing the right color, print, and proportions are key in making your outfit stand out. These tips will not only help you create your own personal style but help you land a second date.

They’re on a date with you. So be you.

Unless you’re going on a blind date, the key thing to remember is that the person you want to impress is already at least somewhat interested in you. They have, after all, agreed to go on a date with you.

So embrace that. This is not the time to try to be someone else.

“You want to wear something tasteful, something simple, without being boring,” says Scott Shapiro, a stylist with Taelor. “You want to show a little personality and maybe a little flair, but also some tact. You don’t want to look like you're obsessed about fashion all the time.”

At the same time, the first date outfit you choose should make you look like the best version of you, not the most relaxed and complacent version. “It's not a job interview, but I think it's good to look professional,” Shapiro says. “It's good to look like you have a career and some sort of income and stability in your life. Nobody wants to date a bum.”

Joanna Medeiros, another stylist with Taelor, agrees. “You want to showcase who you are,” she says. 

Nicole Gibbons, another fashion stylist with Taelor, also emphasizes a clean and put-together look for dating.

“A lot of it has to do with the weather and what you guys are doing. Are you going on a first movie date? Are you going out to lunch? Are you going out to a fancy dinner? Are you going to a concert? But generally you want to look nice and put together, but still show your style and who you are,” Gibbons says.

Instead of wearing your favorite color, wear one that suits you

To show the world – and your date – who you are, the key is to know and accept who you are. That requires taking an honest look at your body type, skin tone and your level of fitness.

Start by considering what colors do, and don’t, work for you.

“You want to choose colors that match your skin tone,” Medeiros says.

To find out what kind of complexion you have, look at your veins. If they look greenish, then you have warm undertones and we recommend wearing mustard yellow and brown. If your veins look bluish, you have cooler undertones. If you have more of a yellow undertone to your skin, try wearing purple, which is a complementary color that will look really great on you. If you have a more red undertone, wearing green or blue is most complementary for you. If you have darker skin, then bright colors (cobalt and bright red) might be a great option to make a statement and can complement your skin tone.

(left) BONOBOS BLUE TEXTURE STRETCH LONG SLEEVE SHIRT 
(mid) BONOBOS OLIVE DOT STRETCH SHORT SLEEVE SHIRT
(right) SURFSIDE SUPPLY BLUE AIRY COTTON BUTTON UP SHIRT WITH FRONT CHEST POCKET

When it comes to choosing what color to wear to make an impression, our stylist recommends sticking with either black or blue when you want to come across as stylish, calm and classic. But if you want to try something riskier, try a red shirt, which will make you seem more bold and confident. When experimenting with color, Taelor’s monthly men’s subscription box can help you try out new colors without the commitment of buying. You can explore all the trendy pieces and see what fits your personality and makes you feel bold.

(left) BONOBOS LAVENDER PLAID STRETCH LONG SLEEVE SHIRT 
(mid) MAVI OLIVE SLIM STRAIGHT CHINO PANT
(right) BONOBOS RED BLUE STRETCH SLIM BUFFALO CHECK FLANNEL SHIRT

Make a statement with a print

Picking the perfect print is a great way to make a statement without a single word. Your style and clothing make an impression and impact before you say anything. Here is a guide to help pick the perfect print that will make the right statement: 

• Floral prints may be a bit feminine, but they also make you seem extremely approachable.
• If you want something fun to chat about, choose a conversational print, like a shirt with tiny dogs or little cactuses all over them. Conversational prints show that you’re a little bit more fun and playful.
• If you want a classic look, our stylist recommends simple stripes or possibly plaid.
• Plaid is more relaxed and makes you seem like you have a flare for an outdoorsy adventure.

(left) RAILS SAND PLAID LONG SLEEVE BUTTON UP SHIRT 
(mid) R2 AMSTERDAM BROWN WITH COLORFUL FLOWER PRINT LONG SLEEVE BUTTON UP SHIRT
(right) KSUBI BLACK AND WHITE ABSTRACT PRINT BUTTON UP SHIRT

Shapiro cautions that prints work best early in dating when a guy avoids being too over-the-top. “Choose a classic button-up shirt with maybe a subtle print on it,” he says. “You want something that's a little bit out of the box without being maybe too overbearing.”

Follow the Rule of Thirds When Thinking About Fit

When you’re choosing your outfit for your date, you want to make sure that your clothes fit your body properly. 

For example, “With a button-up shirt, you want to make sure it’s not too tight around the belly. If it’s too tight, don’t wear it,” Medeiros says. “So I definitely recommend a shirt with more of a stretch. Bonobos have really great stretch in them. The W.R.K shirts have really great stretch in them.”

(left) BONOBOS BLUE PLAID STRETCH SHIRT 
(mid) W.R.K DARK BLUE MEDALLION SQUARE DOT PRINT 4-WAY STRETCH LONG SLEEVE BUTTON UP
(right) BONOBOS TAN AND BURGUNDY STRETCH SLIM PLAID FLANNEL SHIRT 

One way to think about fit is to use the rule of thirds. 

Imagine your body broken down into three different parts: your head and shoulders, your torso, and your legs. You never want to split your body in half. You want to play with the eye, which can be as simple as layering a jacket over a shirt that is a little bit shorter in length than the jacket and wearing these with a great pair of pants. 

The aim is to balance what you’re wearing on the top with what you’re wearing on the bottom. So if you're wearing a more oversized top, it's a good idea to stick to pants that are more straight or slim.

So, for example, if you have a longer torso, it's a good idea to wear high-waisted pants to even out the proportions of your body. If you have a shorter torso, go for mid-rise pants, and try to wear V-neck necklines because they create the illusion of an elongated neck, which will make your torso seem longer.

(left) DONATO BLACK KNIT BUTTONLESS LONG SLEEVE POLO WITH WHITE STRIPE DETAIL 
(mid) JACK & JONES BLACK DENIM SLIM FIT JEANS
(right) MINISTRY OF SUPPLY HEATHER GREY PERFORMANCE FLANNEL PANT

Perhaps nothing is as important when choosing clothes for a date as wearing pants that fit. “I cannot stress this enough. You have to make sure that you have the right inseam for your height,” Medeiros says. If you wear pants with too long of an inseam, “they're gonna punch at the bottom and make you look sloppy.”

Most importantly, when choosing your outfit, try to pick clothes that accentuate your best feature. So if you have great legs, and your first date involves the outdoors, go ahead and wear shorts that really show them off. 

When in doubt, Medeiros suggests asking your date in advance what she’s going to wear. “Not to match, but just to gauge if she's gonna dress up,” she says.

If that seems too forward of a question (if, for example, this is your first date), then Medeiros says the best bet is to “kind of gauge around where you're going. If you’re taking her to a nice dinner. You can almost assume that he's got to wear chinos and a button-up, possibly a tie,” she says. “But if you’re going to mini golf or bumper cars or something like that, I would say probably err on the side of casual because she's probably going to do the same. I don't think she's going to wear a dress to that.

(left) ANTIOCH DARK GREY BLAZER WITH THREE FRONT POCKETS 
(mid) GUIDE LONDON LIGHT GREY BRUSHED HERRINGBONE DOUBLE CHEST POCKET BUTTON UP JACKET
(right) SMF GREEN LINEN BLEND DRAWSTRING SHORTS

You can’t go wrong with the classics

So what do Taelor stylists recommend for a first date night outfit?

“You want to make sure you're not overdressed or underdressed. There’s a good happy medium there of showing up looking like you put some effort into it,” she says, suggesting guys start by choosing jeans or chinos. “Either way you can dress those up. If you were to do a Chino, I would start with maybe a tan or a navy because you can add other colors to it. And then you can do a button up,” she says. “If you wanted to go with a jean, that’s a little bit casual, so you could go with a knit polo. You can pop over a bomber jacket on that.”

Shapiro also suggests avoiding extremes.”Go somewhere in the middle and low-key,” he says. “Usually something like dark wash jeans and a classic button-up shirt work best.”  

 

(left) JACK & JONES BLUE SLIM RIPPED DENIM
(right) MAVI DARK WASH ZACH STRAIGHT LEG DENIM JEANS 30X32

“Definitely button-ups and chinos are good for a first date,” Gibbons says. Don’t pretend to be someone else. “That's especially important for a date because they're there to get to know you.”

Taelor allows you to try out new colors, prints, and styles to experiment with what fits best. Explore the Date Night Capsule Collection curated by Taelor stylists to find out what works best for you. We hope you can leverage our service to land that second date and the date after. The best part is when your date is over, just send the clothes back to us without worrying about the laundry! Rent from Taelor and nail your date! 

By Paul Conley