Start with a strapless maxi dress. I chose striped ones, but any print works. The dress is perfect on its own, or as a cover up for a cute bikini. The espadrille wedges and straw clutch scream “poolside,” as do the sunglasses.

Finish the look with unfussy makeup, like this waterproof mascara, lip gloss, and a lip treatment with SPF to protect your lips from a long day in the sun.

Look #2: The Floral Maxi

This dress is gorgeous, no doubt, but how could you pull something like this off in real life? With the right accessories, this dress goes from runway to romantic dinner date, or even to your spring break getaway!

Products: Liquid Lipstick – BareMinerals, Suede Bag – Express, Dress (L) – Asos, Blue Sandals – Gilt, Dress (Center) – Azalea, Earrings – Lilly Pulitzer, Sunglasses – Nordstrom, Dress (R) – Express, Bronzer – NYX

The off-shoulder silhouette is so romantic, especially in a floral print. To keep it from looking too dressed-up, stick with flat sandals instead of heels, and add a suede bag and sunglasses.

These tassel earrings are fun instead of formal, and bronzer and this hot pink gloss give you that perfect sun-kissed look!

Look #3: The Midi

Yes, I realize this isn’t a maxi dress, but midi dresses can be equally tricky to pull off. How do you know which length to get? What size heels to wear? How do you even accessorize this??

I think the dress in the picture is dramatic enough (look at those sleeves!) that it doesn’t need too many accessories. But we’re going to take a more laid-back approach so that you can wear a midi dress even after your beach vacation.

Products: Dress (L) – Unique Vintage, Suede Jacket – Sans Souci, Block Heels – Aqua Pillar, Necklace – H&M, Nail Polish – Essie, Bag – Macy’s, Eyeliner – NYX, Dress (Center) – DollsKill, Dress (R) – Nasty Gal