This love expert knows exactly what you should wear on your next date

What to wear is an eternal challenge—but never is it so nerve-wracking as in the context of dating. When you’re making an early impression with a potential mate, the pressure is on, and the stakes are super high.

Don’t worry, though. One of our New Year’s resolutions is to solve this problem for you. To that end, we tapped Lisa Ronis, famed matchmaker and former fashion executive, who has great advice on just-right dating clothes that won’t break the bank.

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She brings her expertise to bear in this smart video, and in the shoppable items below. Whether you’re going on a first date, headed out to a party with a newish beau, meeting his family for the first time—or, heck, already coupled-up and want to look great for your honey—this guidance is pure gold.

Dressing for a first date

Decisive and comforting, Lisa has a clear, easy-to-follow equation when it comes to that all-important first date. She takes the insecure inner monologue out of the picture.

“My rule for the first date is black on the bottom,” Lisa says. “Pair the pants with a very feminine top.” And, she suggests you might want to throw a soft jacket over the top “to complete the look.”

On your feet? “Heels are a must,” Lisa says. “They’ll lift you and make you feel feminine. If you feel good, you’re going to look amazing, and you’ve got the guy.”

Floral Top

Choose a pretty print in colors that flatter your hair and eyes. (Photo: H&M)
Choose a pretty print in colors that flatter your hair and eyes. (Photo: H&M)

Shop it: Flowered Shirt, $20, hm.com

Twisted Knot-Front Peplum Top

Show off your curves without feeling overexposed. (Photo: Amazon)
Show off your curves without feeling overexposed. (Photo: Amazon)

Shop it: Twisted Knot Front Peplum Top, $25, amazon.com

Blouse with Smocking

A soft peasant blouse—in the color of love—is perfect. (Photo: H&M)
A soft peasant blouse—in the color of love—is perfect. (Photo: H&M)

Shop it: Blouse with Smocking, $20, hm.com

Shawl-collar Jacket

The shawl collar makes it casual, not work-y. (Photo: H&M)
The shawl collar makes it casual, not work-y. (Photo: H&M)

Shop it: Shawl-collar Jacket, $50, hm.com

Faux-Leather Jacket

A soft, faux-leather jacket over a feminine top gives you that pretty-and-protected feel that adds up to confidence.(Photo: Amazon)
A soft, faux-leather jacket over a feminine top gives you that pretty-and-protected feel that adds up to confidence.(Photo: Amazon)

Shop it: Faux Leather Jacket, $43, amazon.com

Women's Drape-Front Blazer

We love the pretty drape of this blazer. (Photo: Walmart)
We love the pretty drape of this blazer. (Photo: Walmart)

Shop it: Women's Drape Front Blazer, $25, walmart.com

Paper Bag-Waist Pants

Beyond basic black, these pants are shaped to highlight a small waist. (Photo: Amazon)
Beyond basic black, these pants are shaped to highlight a small waist. (Photo: Amazon)

Shop it: Paper Bag Waist Pants, $45, amazon.com

Levi's Women's 721 High Rise Skinny Jean

Sexy skinny jeans that ride high enough to make you feel secure. (Photo: Amazon)
Sexy skinny jeans that ride high enough to make you feel secure. (Photo: Amazon)

Shop it: Levi's Women's 721 High Rise Skinny Jean, $35, amazon.com

Classic Pointed Toe High Heels

Right out of Rita Hayworth's closet—for a mere $27. (Photo: Amazon)
Right out of Rita Hayworth's closet—for a mere $27. (Photo: Amazon)

Shop it: Classic Pointed Toe High Heels, $27, amazon.com

Trary Women's Pointed-Toe High Heel

More of a pointy-toe, for a tiny bit of edge. (Photo: Amazon)
More of a pointy-toe, for a tiny bit of edge. (Photo: Amazon)

Shop it: Trary Women's Pointed Toe High Heel, $23, amazon.com

Dressing for a party date

In our video Lisa offers up a second challenging scenario: dressing to go to a party with this new fella, on a second or third date. Her recommendation? A dress that’s sexy, feminine, and comfy.

If you want to, “you can accessorize in a very simple way that won’t distract him from looking at you,” she adds. But feeling easy and breezy in what you wear is important, so don’t go too short or too revealing. “Make sure when you walk out the door, you’re comfortable—so you can focus on your date, not your clothes.”

Women's Vintage Dress

This beauty checks all the boxes for a party date—at an unbeatable price. (Photo: Amazon)
This beauty checks all the boxes for a party date—at an unbeatable price. (Photo: Amazon)

Shop it: Women's Vintage Dress, $30 to $46 (depending on size), amazon.com

Tunic Dress

In many colors and prints—pick the one that makes you feel like a star. (Photo: Amazon)
In many colors and prints—pick the one that makes you feel like a star. (Photo: Amazon)

Shop it: Tunic Dress, $25, amazon.com

Crochet Yoke Fit & Flare Dress

The crochet detail makes it special. (Photo: Nordstrom)
The crochet detail makes it special. (Photo: Nordstrom)

Shop it: Crochet Yoke Fit & Flare Dress, $89, shop.nordstrom.com

Open Toe Ankle Strap Sandals

Parties usually allow for lots of long, lean posing. These will help. (Photo: Amazon)
Parties usually allow for lots of long, lean posing. These will help. (Photo: Amazon)

Shop it: Open Toe Ankle Strap Sandals, $16 to $35 (depending on size and color), amazon.com

Milisente Evening Bag

Big enough for your essentials, and quiet enough not to pull focus. (Photo: Amazon)
Big enough for your essentials, and quiet enough not to pull focus. (Photo: Amazon)

Shop it: Milisente Evening Bag, $13, amazon.com

Stud Earrings, 10mm Round Cut

You'll use these all the time—not just on dates.(Photo: Amazon)
You'll use these all the time—not just on dates.(Photo: Amazon)

Shop it: Stud Earrings, 10mm Round Cut, $12, amazon.com

Teardrop Stud Earrings

Tasteful effortless sparkle and sophistication. (Photo: Amazon)
Tasteful effortless sparkle and sophistication. (Photo: Amazon)

Shop it: Teardrop Stud Earrings, $12, amazon.com

Meeting the family

Time to meet the parents—or the kids? When it comes to this big relationship step, Lisa has a strong recommendation.

“I feel a sweater dress is the way to go. It’s classy yet elegant and casual,” Lisa says. “I love to pair it with opaque tights and booties with a little heel.” (Don’t you wish you could just keep Lisa at home so she could tell you what to wear every single day? We do!)

Shoes should not be uncomfortable—in fact, nothing you wear should make you uncomfortable. You want to feel like a star. By following her guidelines, scooping up some of the pieces here, and giving each outfit a bit of thought, you can nail it every time.

Lisa sums it up with a smile: “Always put your best foot forward—and just make sure it’s a heel!”

Daily Ritual Women's Wool Blend Turtleneck Sweater Dress


In nine gorgeous neutrals, from soft mauve, to deep navy. (Photo: Amazon)
In nine gorgeous neutrals, from soft mauve, to deep navy. (Photo: Amazon)

Shop it: Daily Ritual Women's Wool Blend Turtleneck Sweater Dress, $33 to $39, amazon.com

Tie Waist Sweater Pencil Dress

We love this casual, fun option, with feminine sleeves. (Photo: Amazon)
We love this casual, fun option, with feminine sleeves. (Photo: Amazon)

Shop it: Tie Waist Sweater Pencil Dress, $24, amazon.com

No Nonsense Women's Super Opaque Control-Top Tights

When you wear tights with a sweater dress, be sure the tights are "slippery," so the dress can move freely. (Photo: Amazon)
When you wear tights with a sweater dress, be sure the tights are "slippery," so the dress can move freely. (Photo: Amazon)

Shop it: No Nonsense Women's Super Opaque Control-Top Tights, $7, amazon.com

LifeStride Georgia Booties

Sleek and walkable, these comfort booties are also rich in style. (Photo: Zappos)
Sleek and walkable, these comfort booties are also rich in style. (Photo: Zappos)


Shop it: LifeStride Georgia Booties, $35 (Was $70), zappos.com

Visit Lisa’s site for even more dating tips!

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