What to Wear on a First Date? We Asked the Experts!

What to wear on the first date? It’s a dilemma that we single gals have been trying to solve for decades! (And one that our readers have asked us about on several occasions!) Sure, to some, it sounds like a no-brainer but when it gets down to the wire, we all experience some form of first date wardrobe panic when the “dress to impress” pressure is on!

To help us finally get clarity on the issue, we brought in a few experts: Lisa Morrison, dating expert and matchmaker at It’s Just LunchJess Kirby, style blogger behind Prosecco & Plaid; and Jamie Krell, on-air fashion correspondent, to join us for a virtual roundtable discussion.

Single ladies, grab your notebook—you’ll want to take notes!

Q: First off, do you have any “first date” style rules you abide by? 


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Lisa: Always check out the venue online to get a feel for the setting! (I always do this for my clients.) A great rule of thumb for the first date: Choose a color or outfit that you are often complimented on.

Choose a color or outfit that you’re often complimented on.

Jess: Comfort should be your first priority! The last thing you want to do is be fidgeting with your outfit—there are more important things to be thinking about!

Jamie: Let location be your guide–your look should reflect your environment! Also, pick one best asset to show off and that’s it. For example: Do you have great arms? Wear a strapless maxi dress. Great legs? Wear shorts or a skirt. The bottom line—too much skin can actually be a turn off and look like you’re trying too hard.


Q: Are there any style don’ts to avoid?

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Lisa: Don’t show too much skin! Avoid extremes like overly trendy outfits or heavy makeup. Natural and minimal is always best for the first date.

Jess: I always say more is more–and by that, I mean don’t give it all away on the first date! If you wear something short, balance that out with long sleeves and a low heel. If you decide to wear something backless or low cut in the front, wear it with a maxi skirt or jeans.

This might sound obvious, but give yourself plenty of time to plan out what you’re wearing!

Jamie: This might sound obvious, but give yourself plenty of time to plan out what you’re wearing. (And enough time to steam or iron your outfit beforehand!) Being disheveled and stressed out until the second your date picks you up is no way to start out! Also, wear something that fits you! It shouldn’t be too loose or oversized—something that shows off your figure but isn’t too tight.

(Editor’s note: If it requires sucking in, constant adjustment, or double-stick tape, leave it at home!)


Q: What would you wear to a casual daytime coffee date?

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Lisa: From jeans to a casual dress, my best piece of first date advice: Make sure it’s comfortable.

The ultimate goal? To achieve the effortless “I just threw this on” vibe.

Jess: Casual staples: Jeans, converse or flats, t-shirts, and sunnies are great options for a casual daytime setting.

Jamie: An easy dress with some sort of jacket (depending on your style—a leather cropped bomber, a cardigan, a denim jacket, etc.) is always a great outfit combination. You can do flats or wedges depending on the setting and what you’re most comfortable in. The ultimate goal is to achieve the effortless “I just threw this on” vibe.


Q: What about what to wear on a dinner date?

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Lisa: Stand out on a more formal occasion by adding a statement piece of jewelry or a fun accessory as a conversation starter. Don’t be tempted to wear anything that you can’t walk in, eat in, or breathe in!

Don’t wear anything that you can’t walk in, eat in, or breathe in!

Jess: Comfort is key no matter what. If you feel good in what you’re wearing you’ll look good; confidence is everything. For a dressy dinner date, I’d go with a shift dress or skinny jeans, a silk camisole, blazer, and heels. For a casual dinner, boyfriend jeans and a cute blouse or tee are always a great bet.

Jamie: For a dinner date, go for a great pair of skinny pants that show off your figure (classic black leather or fitted jeans) with a nice silk tank or blouse and clutch. You can add a classic nude or black heel to dress up your look—a nice mix of dressy meets relaxed. For makeup, it’s all about the balance. Not too much, but not too little. You want to look like you put in the effort to look nice, but don’t want to over do it! You want to enhance your features, not overwhelm them.


Q: What would you wear on a post-work drinks date?

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Lisa: Most important in this instance is not what you’re wearing but that you can relax and get out of work mode! For a mix of office appropriate meets date night, opt for a dress or skirt with a feminine top under a jacket. (You can remove the jacket when you leave the office!) Switch that big work bag to a clutch for an easy transition to evening.

Bring something to loosen up your work clothes a bit.

Jess: Loosen up your work clothes a bit. If you wear a pencil skirt and blazer to work, change into a cute t-shirt and add red lipstick.

Jamie: Don’t worry about being business casual! Work attire is totally fine. A classic, fitted blazer is perfect for the occasion when worn the right way!


Q: Any parting words for date style advice?

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Lisa: Be confident and be yourself. This is what will make a great first impression and guarantee a second date! (That is, if you want one!)

Jess: I can’t say it enough—wear what makes YOU feel good. At the end of the day, it’s all about confidence. If you feel good in what you’re wearing, it’ll show.

Wear something that truly makes you feel like the best version of yourself.

Jamie: You really want to represent yourself in a true, real way. Don’t show up in a t-shirt and ripped jeans if you’re usually in feminine dresses and vice versa. Wear something that truly makes you feel like the best version of yourself. Because when you do that, you will have more confidence. And the more confidence you have, the more you will smile, the more you will engage and chances are, the more dates you’ll have!


What style advice do you have when it comes to dressing for a first date?