Foolproof Date Outfits That Work For Any Occasion

Familiar with this scenario? A guy—maybe a friend of a friend you’ve been eyeing for a while—finally calls and asks you out. You say yes, and he says, “Great, I’ll pick you up at 8.” Great! Click. End of conversation. Except not so great, because you failed to ask any follow-up questions (like, um, so where are we going?), and now you have no idea what to wear. 

And that’s where we come in. If you, like us at times, are unwilling to bite the bullet and make that follow-up call, we’ve come up with six foolproof outfit ideas that perfectly walk the line between casual and dressed-up, so you’ll feel totally at ease in your outfit no matter where you’re going.

Scroll through to see our suggestions! 

1. Trench Coat + Romper + Cross-Body Bag + Booties

Photo:

Tuula Vintage

For a look that’s just sexy enough for a date yet still classic, pair a long trench with a black romper (or LBD). A cross-body bag and booties will dress your outfit down just enough, so you’ll be dressed appropriately for any outing.

2. Printed Top + High-Waisted Pants + Statement Clutch + Chunky Heels

Photo:

Style du Monde

To avoid looking like you’re going to work in your button-down, try tucking it into form-fitting, high-waisted pants and pairing it with a statement clutch. Chunky heels are always a safe date-shoe choice, as they can read both dressy and casual.

3. Hat + Printed Dress + Cross-Body Bag + Matching Shoes

Photo:

Style du Monde

If you’re a hat girl, dress one up by wearing a printed dress of your choice. For easy accessorizing, match the colour and hardware of your bag to that of your shoes. And if you can’t decide between heels and flats, then this interesting tip can help.

4. Statement Necklace + Midi Dress + Plaid Shirt + Heeled Booties

Photo:

A Love Is Blind

For a feminine-grunge combo that works for day or night, combine a classic black dress with a statement necklace (gold is a great go-to) and plaid shirt. Finish the look with heeled booties, for a little extra height.

5. Moto Jacket + Button-Down + Distressed Denim + Heeled Sandals

Photo:

Style du Monde

If your taste is edgy, show it by pairing a moto jacket with distressed jeans and cool accessories (like Hillman’s to-die-for Mark Cross bag). A crisp button-down and heeled sandals will give the look a put-together touch without taking away from your personal style.

6. Oversized Blazer + T-Shirt + Miniskirt + Booties

Photo:

Man Repeller

This outfit is all about balance. The miniskirt is feminine and flirty, while the T-shirt gives it a casual element, and the jacket adds a menswear-inspired touch. As for the flat booties, they’re the perfect way to dress down the skirt, while keeping the look polished.

Will you be trying any of these looks out on your next date? Tell us which one in the comments!