Win the Day

First Date Outfit Ideas for Summer: How to Dress to Impress

by Drew Dagan


Summer is an exciting time for dating: the weather instantly puts everyone in a good mood. First date outfit ideas for summer don’t need to be overly complicated—the most important thing is to express your personality and show off your polished style. It’s also important to take the location into consideration. An easy way to figure out how to dress is to look up the location online and check out atmosphere or interior photos, as well as the menu, if applicable.

There’s so much to think about already, such as what to ask and what to share. That’s why we’re offering our outfit suggestions—so you can concentrate on what really matters: the conversation and connection.

For the Drinks Date

An invitation for a glass of wine or a cocktail is a great way to get to know someone in a relaxed setting. If the intention is to have a drink (and you’re unsure about dinner), keep the outfit neutral between casual and formal. A flirty skirt with movement can be paired with a tee or tank in a solid color and accessorized with face-framing earrings. Shoes can run the gamut from high heels to chic sneakers, dependent on location (think: heels for a rooftop setting and sneakers for a brewery). A small wristlet or clutch is a great flourish to finish it off.

floral printed knee length asymmetrical skirt

For the Brunch Date

Brunch dates are growing in popularity thanks to their relative affordability and easy time commitment. A printed pair of pants in a silky fabric like jersey is a good starting point for a brunch date, and you can top it off with a simple shell or tank. Depending on the location, you can add either a denim jacket or a gauzy scarf to combat unpredictable air conditioning situations. Low block heels or wedges are appropriate for daytime but still elongate your legs. Come prepared with cute sunglasses in case you’re seated on the patio.

woman in black and white floral printed pants

For the Activity Date

Non-traditional dates like farmers market strolls, riverfront walks, or window shopping are a great way to get to know someone while allowing for plenty of opportunities to fill in any gaps in conversation with people-watching. If you’re going on a daytime date that involves an activity, consider shorts for maximum mobility. Balance out showing off some leg by pairing it with a top offering a little more coverage, such as an off-the-shoulder tee or ruffle-sleeve blouse. Ballet flats, espadrilles, or feminine sneakers are all appropriate footwear depending on the activity. Finish the look with a practical crossbody bag, perfect for keeping your hands free.

woman in five inch smooth front shorts in lavender

For the Dinner Date

There’s nothing wrong with a traditional dinner date—simple can be best sometimes. A high-low maxi dress is perfect for many restaurant environments and can be dressed up and dressed down. If it’s a white tablecloth restaurant, add high heels and face-framing earrings; if it’s more casual, try espadrilles or ballet flats with a cuff bracelet. An additional wrap or thin cardigan is not only practical, but looks beautiful draped over your shoulders in candlelight.

woman in black and white high low floral maxi dress

With a little planning, first date outfit ideas for summer are a breeze. The most important thing to remember is to be yourself—and let your personality shine, no matter what you are wearing.

Featured in this article:

Floral Asymmetrical Skirt, $110

Jersey Knit Pants, $89

5-Inch Smooth Stretch Shorts, $49

Flutter-Sleeve Chiffon Floral High-Low Maxi Dress, $165

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