31 May Outfit Ideas That'll Infuse Your Morning Routine With Joy

Come May 1, I love seeing the viral Justin Timberlake meme “It’s gonna be May,” all over my Instagram feed — it never gets old. But internet jokes aside, there’s a lot of excitement in store over the next month. With Memorial Day Weekend creeping up, perhaps you’re looking forward to an afternoon at the beach; maybe your group chat is blowing up with messages about checking out a new rooftop bar this weekend. Regardless of the specific excursions on your docket, you’ll want fun May outfits lined up and ready to go once the plans are confirmed.

For the most part, you’ll soon be able to leave your house sans wool coat now that there’s less fear of a brisk chill ruining your day. As a result, more attention can be placed on curating the rest of your look. Looking for specific insights into getting dressed these next few weeks? Well, the sheer look isn’t dying down any time soon, so give a see-through blouse a whirl. And on the dress front, the designs this season are focused on voluminous silhouettes and ‘60-inspired motifs. To accessorize your May ‘fits, consider out summer’s top jewelry trends — must haves include pearls and candy-hued pieces to liven up any look. Lastly, take advantage of open-toe shoe weather by slipping into a pair of barely-there sandals.

Find more style inspiration in the 31 outfits ahead, one for every day of this month.

All-Gray Look

According to influencers on Instagram, the moody color trend is sticking around for summer. To keep your look from appearing too heavy, opt for a miniskirt in the shade and balance it with a lighter, brigher color.

One-Shoulder Dress

Are you attending a rooftop party, backyard wedding, or oceanfront dinner soon? If yes, tap a one-shoulder dress as your plus one for the outdoor occasion.

Standout Jewelry

Fact: A statement earring is the key to taking your look to a whole new level.

Versatile Black Top

A black, off-the-shoulder top can seamlessly take you from work to dinner. Simply swap out relaxed trousers for a dressy skirt — it’s that easy.

Matching Set

Break the dress mold at your friend’s wedding by opting for a textured matching set. You get bonus fashion points if the two-piece comes in a fun springtime hue, like pastel pink or blue.

Little White Dress

Trade in your LBD for a nonchalant white dress, like this sweet eyelet style. Accessorize with playful sandals, and you’re set for the day.

Evening-Out Top

Is your closet short on sultry going-out looks? If yes, a bustier is an foolproof addition to any top collection.

Understated Separates

On days when nothing in your closet is speaking to you, reach for a white tank and denim shorts. The combo is effortless off-duty dressing at its finest.

Graphic Tank

Now that your statement tops are no longer buried underneath layers of clothing, let them take center stage. For example, a graphic tank with neutral bottoms is a formula worth trying.

Printed Blouse

For those who want to get a tad more adventurous with their look, a printed blouse is the way to go. Whether you choose a floral or checkered motif, the look is a surefire way to shake up your outfits.

Busy Pants

May allows for the opportunity to look cute at the farmer’s market. Bold sunnies? Check. Woven tote? Check. Gingham pants? Check, check, check. The only thing fresher than the produce is your look.

Everyday Jeans

There’s a reason jeans are considered a wardrobe essential — they go with absolutely everything. Should you need a bottom to ground a bright top, you can always count on your favorite true blues.

Playful Pearls

We’re going to let you in on a little styling secret: A pearl necklace can transform any look. Here, the piece gives a quirky combination an air of elegance. And if you have a laid-back outfit that could use some amping up, the polished accent will do the trick, too.

Simple Swimsuit

Here comes the sun — and, in turn, swimwear. ‘Tis the season to hit the pool in style, and a black one-piece look is a no-fail option.

Delicate Lace

You may not need to layer your tank over a tee, but it’ll certainly feel fun to do so. Allow your undies to subtly show, too, for an adventurous street style-approved look.

Knit Bucket Hat

There’s bound to be a few chilly mornings this month (ugh). Luckily, though, low temps are no match for a colorful knit bucket hat.

Tennis Look

Whether you’re a natural on the court or have yet to learn how to hold a racquet properly, it’s hard to resist the allure of an athletic skirt. Team it with a sporty tank for a tenniscore vibe.

Black Matching Set

Vibrant colors aren’t for everyone, and that’s OK. There are still plenty of breezy neutral looks for summer, like this matching set from Dôen. Pair the two-piece with your fave polished accents.

Rosette Accent

If you love 2023’s rosette trend, try out the look via a floral belt. Whether you wear it with jeans and a tee or with a dress, the accessory gives every outfit a romantic feel.

Easy Shoes

Ugg’s beloved Tasman slippers haven gotten the clog treatment, and it’s time to take advantage. The look boasts a removable sock; therefore, you needn’t to worry about finding a matching pair in your drawer.

Closet Essential

A white button-down is a closet MVP. Wear yours with slouchy denim, an itty-bitty miniskirt — you name it.

Cropped Cardigan

Sun’s out, midriffs out. Indeed, this month marks the beginning of crop top season. Tip: Balance out a tiny sweater with high-rise pants.

Crochet LWD

Is your closet missing a little white dress (LWD)? If yes, consider nabbing a summery crochet look. The number is suited for pool parties and beach gatherings.

Yellow Bag

Get in a sunny state of mind with the help of a bright yellow handbag. As for your outfit, go for a feel-good floral dress for a serotonin boost.

All-Day Pajamas

PJs you can wear 24/7? Yes, they exist — because boxer shorts are outdoor-appropriate these days. Dress up the bottoms with a going-out top for a casual-yet-chic daytime look.

Colorful Set

RSVP’d yes to a swanky summer event? An attention-commanding set is sure to win you compliments.

Breezy Midi

An easy printed midi dress belongs in everyone’s summer rotation. A style hack to try is contrast the romantic vibe with a sporty sneaker.

Must-Have Mary Janes

Sweet and sophisticated Mary Janes are so easy to fall in love with. Give the schoolgirl-esque shoe a sultry touch with an itty-bitty miniskirt.

Red Gown

Yes, the bright red color trend is poised to dominate this summer, at least if celebrities and influencers have anything to say about it. Test out the hue with a floor-length gown for a wedding or work event.

Striking Sandals

Nothing says you’re ready for summer quite like an orange shoe. Pro tip: Team the piece with another citrusy shade.

Denim On Denim

Double the denim, double the fun. Add a splash of color to the Canadian tuxedo with a neon bag and pastel shoes.