What should I wear to this? How many times have we all stood in front of our closets and whispered those words into the air? I get it. Even if we have a well-stocked wardrobe with the perfect pieces for our everyday lives, we still come upon the occasional event or activity for which we just don’t know quite how to dress. Today I’ve got a great suggestion for what to wear when you don’t know what to wear. And yes, it’s a “one size fits all” kind of solution that will absolutely work 99% of the time.
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That said, if this simple solution to that age-old question doesn’t work for you, I hope you’ll let me know in the comments what you wear when you just don’t know what exactly you should wear for an occasion. Your suggestions and comments are welcomed!
What to Wear for Any Occasion
As a woman, I’ve noticed that a dress is not only a simple solution to this outfit dilemma; it’s also a beautiful one. You’ll always look your most feminine and pretty when you wear a dress. Especially one that works nicely for your body shape and coloring.
Today I’m wearing a stunning deep blue cheesecloth fit and flare dress from Me+Em. But the point here is that choosing to wear a dress is indeed the smart solution to what to wear when you don’t know what to wear.
Why is a dress such an optimal solution to this common quandary? Because a dress makes you look beautiful and feminine. When you wear a dress you automatically look like you’ve put a little thought and effort into your attire. But, as long as you accessorize impactfully and simply, your outfit will also have that desirable “effortless” vibe that says, “I knew exactly what to wear all along.” No one will know that you ever had that moment when you didn’t quite know what to wear.
When you wear a pretty but fuss-free dress, especially on a summer day or evening, you can accessorize in a way that rises to the occasion. I’ve worn cognac sandals and bright, feminine jewelry to complete my dress for a mid-morning brunch, a lunch with the ladies, a bridal or baby shower, a live performance in the park, an afternoon garden tea or a host of other warm weather occasions.
But I could swap in slingback pumps or heeled sandals for a more elevated look. And I could change out my straw satchel for a pretty clutch. Add a linen or silk wrap and I’d have an outfit perfect for an evening date, dinner with friends or drinks in your neighbor’s backyard.
I think the key to wearing a dress for most summer occasions is to keep the look simple. Especially in 2026, the key messaging seems to be around basic, but elevated dressing. So this one-and-done formula helps you to master that aesthetic with ease and grace.
Do you have a few beautiful, simple dresses in your closet for summer? Wear them! Enjoy the feminine feeling you get when you slip on a pretty dress and sandals. To keep your look fresh and carefree, wear your dress over the perfect bra and a pair of Thigh Society slip shorts. They help prevent thigh chafing, but they also take care of pesky panty lines and act as a slip against your skirt.
If you don’t have a dress in your closet that you could turn to when you don’t know what to wear, I’ve got quite a few in the shopping widget below for you to consider. I’ve also got links to everything shown in my outfit in the widget.
Thanks so much for dropping in for a little style inspiration. What do you think about my solution to the “what should I wear to this” problem? I’d love to hear your thoughts in the comments below.
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Blessed for My Day
I value loyalty in a person. When someone sticks beside me through thick and thin, good times and hard, glory and gossip, I am so appreciative. What a blessing to have people who love you enough to stay true when others fail you. By this time in our lives, most of us have experienced our fair share of fair weather friends, but hopefully we can all say that we’ve had true friends and devoted family members, too.
I guess the bigger question is what kind of friend and family member have I been? Let’s pause and ask that hard question of ourselves today. More than likely we have a few regrets over times that we didn’t stick around when we should have. But there’s still room for improvement. We can commit to hear people out, to give grace, to avoid gossip and hearsay, to assume the best instead of the worst and to love to the bitter end. And having that kind of commitment to other people really begins with a heart devoted to the Lord. God values commitment – to Himself and to others. And as we become more like Him we will strive to stay committed to our relationships as well.
Many a man proclaims his own loyalty,
But who can find a trustworthy man?
A righteous man who walks in his integrity—
How blessed are his sons after him. ~ Proverbs 20:6-7