What to Wear on Summer Dates

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Summer is here at last! Meaning that it’s time to dust off the hot-weather wardrobe. When the weather is this gorgeous, no one needs stress about what to wear on dates. So we asked Jennifer Kelton, CEO/Founder of, to offer some outfit tips and suggestions for key outings this season.

A Picnic Date in the Park

Dress for the Date suggests moving outside of the traditional jeans and t-shirt look for both men and women.

For ladies, a solid colored dress with some Converse-type sneakers or embellished sandals with your hair down speaks outdoor goddess, yet relaxed.

While it’s not a swanky night out on the town, you’ll still want to look like effort has been made, in an effortless way. Plus, if your day date continues into the evening, you can easily throw on a black wrap, some strappy heels, and a chunky elegant necklace (which you just so happened to have in your over-sized tote bag).

For the guys, please step back from the plaid shirts — they’ll likely clask with the picnic blanket. Keep it classy and casual. Think classic chinos and a Havana shirt matched with a stylish retro Cuban hat (if hats are your thing).

A Baseball Game

Wait, was that you and your date flashing across the jumbo screen Kiss Cam? Why yes it was! Which is why Dress for the Date suggests to get your fashion tips from Jay Z Beyonce as seen at a recent Yankee Game

While Jay Z is wearing a baseball-cap, he also looks put together with a statement men’s jewelry piece, a crisp white t-shirt, a cardigan and jeans.

Beyonce has moved away from what one would expect to see at a ball game, which speaks confidence. Dress for the Date is not suggesting that you show up wearing a low-cut cocktail number, but rocking a sporty blazer with jeans and your team’s t-shirt underneath will set your look apart.

Dinner with His/Her Family

A loaded date? Perhaps the most loaded date. You’ll have enough to think about — don’t let any “Oh my god, what am I going to wear!?” panic add to the mix.

For women, Dress for the Date suggests the best and easiest option: a basic black dress.

It’s better to stick with a go-to dress that you already feel comfortable and confident in, rather than the latest throwaway trend.

If you do decide to find yourself a new “I’m meeting the family outfit,” DFTD suggests opting for a timeless, classy option, such as this wrap dress by DVF. Bonus: a dress like this can easily become a staple in your wardrobe.

Diane von Furstenberg Bentley Faux-Wrap Dress, Black

For men, DFTD suggests that you opt for smartly tailored separates, such as this Theory look. It has the perfect balance of relaxed and tasteful.

Theory Jaiden Cotton Blazer, Zack Striped Sport Shirt & Raffi Cotton Pants

Sunset Dinner

You and your date are alone, the sun is setting and it’s all so very breathtaking. The last thing you want to think about is the fact that you’ve squeezed yourself into clothing that’s too tight.

For women, stay away from pants. Think chiffon and silk and stick with a mid-length or long skirt, or try a playful, sexy dress.

For men, keeping with the romantic vibe, DFTD suggests a lightweight linen sweater or bib-front long-sleeve shirt. Pair it with lightweight poplin pants.

Afternoon BBQ with His/Her Friends

The BBQ grill is fired, the long week has come to an end, and you and your date are looking forward to a day of relaxation, beer and a cookout. Now is the time to pull out the shorts and t-shirts. It’s all about casual comfort.

Ladies, DFTD encourages you to bring a stylish sun hat. They’re sexy and fashionable, and sun protection is crucial. Guys, reach for your favorite go-to baseball cap, (as long as it doesn’t have sweat marks and smell like a locker room). A pair of aviators looks great on both men and women, and also goes great with a swimsuit.