Date Outfit Ideas for Summer

Style Tips

date outfits for all occasions

Whether it’s a first date or a date with someone you’ve been with for 17 years, you’ll want to feel sexy. Do you know what makes you feel hot? Have you thought about it lately? 

Before planning your outfits, it might be good to take a few steps back and really figure out what feeling sexy means to you, especially when we have been dressing up way less often for the last year. If you need some help getting started, head over to my Style Resources page and check out my instantly available How to Find Your Authentic Sexy Style Mini Course.

Here’s some date outfit inspo for many different types of dates and pieces to complete your date looks this summer!

Dinner Out

It’s been so long since we’ve been able to go out on a proper dinner date, I vote that we bring all of those sexy vibes. 


Both Tony and I have seasonal allergies, so the idea of a picnic has never seemed as romantic to us as it may to other people. We have done picnics on the beach, which I highly recommend (if you can avoid the fearless seagulls of the Jersey shore). If you’re doing a picnic on the beach, I would suggest a cute dress, romper, or jumpsuit over a bathing suit. Cupshe has a lot of stylish and fun bathing suits – especially one pieces that would be great for a beach date! (Fun fact: Cupshe carries bathing suits up to a size 4X! Yay size inclusivity!)

Outdoor activity (kayaking, hiking, horseback riding, etc.)

Fun jewel toned leggings with pockets – leggings help to prevent against lots of bug bites

Cute bathing suit without the fear of a wardrobe malfunction (translation: avoid bathing suits with minimal coverage, stringy straps that can be easily moved, strapless, or any really low cut tops)-This scoop plunge top from Aerie is adorable and perfect for watersports.


Brunch outfits always make me think of floral dresses, small prints, or light colors. 

Brunch to Museum

Belted Bodycon midi dress – belted wrap dresses like this are really on trend right now, they are also so perfect if you’re uncomfortable highlighting your stomach in a traditional bodycon dress, the belt creates and/or defines your waist, and brings the attention away from your stomach. A lighter colored dress like this one, in a ribbed fabric, makes it more casual, perfect for a daytime date like brunch! Pair it with platform sandals or platform sneakers (I own these and LOOOVE them), so you can comfortably wear them from brunch to your next destination, like a museum or an outdoor market.

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