Advertisement
Slideshow will continue in seconds. Click to skip
Click through for 31 perfect May outfits, one for each day of the month (and their shoppable counterparts, too!).
May 1

Until it’s truly warm enough to wear your favorite white summer dresses and skirts solo, cover up with a fun printed bomber jacket. This one’s even reversible!

Click through to shop the look.

May 2

So it’s settled, then: olive green and royal blue is our favorite new unexpected color combo.

Click through to shop the look.

May 3

Is there anything more springtime-appropriate than a playful lip print?

Click through to shop the look.

May 4

Everyone’s tying their flannel and chambray button-ups and jackets around their waists these days; why not flip the trend on its head by turning yours sideways? A bold striped layer adds an especially striking touch.

Click through to shop the look.

May 5

Spice up an outfit of head-to-toe springtime whites with a punchy hit of grey leopard.

Click through to shop the look.

May 6

Proof that multiple fringe-trimmed outfits can work together beautifully—without making you look like a Coachella reject.

Click through to shop the look.

May 7

Want to step out in top-to-toe pastels without being mistaken for an Easter egg? Add in a few well-placed nude accents to instantly tone down the overall look.

Click through to shop the look.

May 8

Unless you're Cher Horowitz and have a white sheer jacket on hand (and a Beverly Hills house party in 1994 to attend), top your skimpiest dresses with a leather bomber. The style adds just enough androgynous attitude to keep the outfit from feeling too risqué.

Click through to shop the look.

May 9
It's warm outside, but not quite warm enough to go whole hog on tank tops and shorts. Instead, enjoy this beautiful 65-degree moment with the same sort of transitional stuff you wore in April–minus the cumbersome coat.
Click through to shop the look.
May 10
Swapping out your jeans for relaxed red trousers is a simple way to make your weekend outfit more polished (but no less comfortable).
Click through to shop the look.
May 11
What, your skirt only has one layer? It's time to fix that.
Click through to shop the look.
May 12
Although it's been over a year since Miuccia Prada sent her gingham-tastic collection down the runway, the look still feels fresh. Make it work for May weather by coordinating a colorful checkered pencil skirt with a lightweight pullover.
Click through to shop the look.
May 13
Don't be afraid of wearing a full-length lace dress during the day! So long as you have laid-back accessories–like a sunglasses and a loosely tied silk scarf–and slightly undone hair, the look works.
Click through to shop the look.
May 14
On that first glorious day when it's warm enough for both bare shoulders and legs, celebrate with the most cheerful minidress in your closet.
Click through to shop the look.
May 15

Nothing says Palm Beach weekend like a palm printed dress.

Click through to shop the look.

May 16

Go ahead, match your lipstick to your shoes with bright red heels.

Click through to shop the look.

May 17

White shorts get flirty with scalloped lace detailing.

Click through to shop the look.

May 18

Not ready to try full-on mesh? Keep it to your shoes to add a peekaboo touch.

Click through to shop the look.

May 19

We love monochromatic white on white, but take the look to the next level by adding similarly snowy accessories.

Click through to shop the look.

May 20

Since summer is here, it's time to try out that jumpsuit trend.

Click through to shop the look.

May 21

The Canadian tuxedo gets updated with a light blue midi skirt.

Click through to shop the look.

Peeking out from a collared shirt, a chunky gold necklace looks oh so chic.

Click through to shop the look.

May 23
Presenting: a monochromatic grey look that comes across as anything but monotonous.
Click through to shop the look.
May 24
Oh, how we adore this slit leather skirt juxtaposed with an edgier printed tee.
Click through to shop the look.
May 25
Epitomized by Kenzo's now-infamous design, the tiger tee is a fun alternative to a basic solid t-shirt or sweatshirt.  
Click through to shop the look.
May 26
A solid denim jacket will never go out of style, especially if you invest in one with perpetually cool leather trim.
Click through to shop the look.
May 27
Accessorize a prim knee-length skirt with a pair of of-the-moment, athletic-inspired slides.
Click through to shop the look.
May 28
If you haven't already picked up on our undying love of shirtdresses, please note that it's an absolute spring must-have for the more femme dressers among us.
Click through to shop the look.
May 29
Give your well-worn plaid shirts a break during the warmer months with a lighter, gauzy plaid dress alternative.
Click through to shop the look.
May 30
Nautical or nice? Patriotic, preppy and beachy color combinations need not be restricted to the Fourth of July.
Click through to shop the look.
May 31
Gingham's ladylike and old-timey vibe is a guaranteed home run come spring, especially when worn head-to-toe for a definite retro look.
Click through to shop the look.