31 Comfortable Summery Outfits That Will Get You Ready For The New Season


There's still no straight answer as to when you'll be able to get your hair cut, work out at the gym, or finally host a dinner party with your friends. But, you can still look forward to warm weather and sunshine arriving this month. You'll be able to open your windows, sit on your patio (or fire escape) dressed in comfortable summer-worthy outfits that you'll want to break out for months to come.

Your agenda for the month of May includes Zoom calls, virtual workouts, and puzzles with your quarantine clan, but now that you've established a routine, switch things up when it comes to dressing for these occasions. While you're working for home, consider parting ways with your everyday sweats and opting for comfy ribbed pants instead. Or if you're seeking both comfort and elegance, pull out your favorite summer dress. And if your roommates are having a Friday game night, show up to the living room in a soft silk blouse (or go outside the box and wear your silk scarf as a top).

To help you find the perfect May outfit — no matter where the month takes you — keep scrolling to find 31 comfortable summer outfits. Remember to stay positive and keep dressing fun.

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Comfortable Summer Outfit: Dress Up For Dinners At Home

A silk floral dress around the house? Why not! Wear the luxe piece to date night at home with your spouse or to a family dinner.

Comfortable Summer Outfit: Go For A Comfy Mini Skirt

Instead of gym shorts, opt for a mini skirt in a cotton fabric once the weather gets warm. If you're feeling extra fancy, slip on a pair of heels.

Comfortable Summer Outfit: Transition Your Short Sleeve Sweater

If you aren't ready to let go of your sweaters just yet, opt for a short sleeve iteration. And to make the look summery, chose a knit with floral embroidery.

Comfortable Summer Outfit: Use Your Scarf As A Top

Get creative by using your silk scarf as a top. To make the look laidback for home, slide on a pair of flip flops.

Comfortable Summer Outfit: Head-To-Toe Sporty

Between walking your dog and going on runs, a full workout outfit will come in handy. For rainy days, choose an ensemble in a waterproof material.

Comfortable Summer Outfit: Style Your White Tee With Slippers

A simple white tee coordinates seamlessly with anything in your wardrobe, but make the look suitable for at-home with comfy trousers and slippers.

Comfortable Summer Outfit: Choose A Cozy Set

On hot May days, try out a knit bra and matching pants. For some extra coverage that won't fully hide your bra, throw a sheer top over it.

Comfortable Summer Outfit: Take Your Graphic Tee To The Next Level

Elevate a comfy graphic tee by pairing it with bold floral pants.

Comfortable Summer Outfit: Bike In Your Sporty Basics

Grab your bike and ride around the neighborhood in sporty separates. A little sunshine is *just* what you need.

Comfortable Summer Outfit: Pops Of Green

Embrace both pastels and bold hues this season. Green is an excellent hue to try out in different shades.

Comfortable Summer Outfit: Lay Around In A Crochet Dress

Try out a light piece meant for summer, like a crochet dress. Couple the dress with grungy black boots for a cool combo.

Comfortable Summer Outfit: Forget The Jewelry

Give your stylish tank the attention it deserves by skipping jewelry and accessories all together.

Comfortable Summer Outfit: Mix Prints

Mixing together contrasting prints is both eye-catching and on-trend. You'll want to look cute this May, even if you'll just be at home snacking on fruit.

Comfortable Summer Outfit: Have Fun With Color

Tie-dye is once again having a major moment. Couple the exciting print with bright loungewear.

Comfortable Summer Outfit: Stick To Neutrals

Incorporate various neutrals into your outfit for a polished approach to summer dressing.

Comfortable Summer Outfit: Lightweight Maxi Dress

Whether you wear this dress in bed or as a cover-up by the pool, your mood will instantly be brighter.

Comfortable Summer Outfit: Break Out Your Denim Shorts

While they might not be the comfiest bottom you own, your denim shorts are ideal for running errands outdoors.

Comfortable Summer Outfit: Sunbathe In A Strapless Tank

Rib pieces are perfect for lounging around at home, and if you're looking to sunbathe on the patio, pick one that's strapless. Just be sure to lather on SPF prior.

Comfortable Summer Outfit: Feel Cozy-Yet-Cute In Knit Mini Dress

A knit mini dress is equal parts cozy and cute. Select one with floral embroidery for a delicate detail.

Comfortable Summer Outfit: Business Meets Casual

For your next Zoom meeting, remain business on top and opt for causal on the bottom.

Comfortable Summer Outfit: Dress Up Your Athleisure

Instantly dress up your athleisure by throwing a printed kimono on top.

Comfortable Summer Outfit: Matching Short Set

A matching set is an easy way to look put-together in a pinch. White on white is a cool look, just be careful to avoid any messy snacks.

Comfortable Summer Outfit: Leave Your Pajama Shirt On

No need to completely change in the morning. Keep on your pajama top, but dress it up with denim shorts and espadrilles.

Comfortable Summer Outfit: Make A Vintage Dress Feel New

Breathe new life into a vintage dress by coupling it with a beachy straw hat and chic flats.

Comfortable Summer Outfit: Experiment With A New Print

If florals aren't your thing, experiment with colorful checkered print instead.

Comfortable Summer Outfit: Style Your Briefs

If you don't feel like putting on real pants (understandable), wear your comfy boy shorts with a punchy yellow sweater.

Comfortable Summer Outfit: Make Your Sweats Feel Cool

Don't worry, sweats are still a go-to for the month of May. But instead of a tee, try pairing the loungewear with an oversized button-up.

Comfortable Summer Outfit: Heeled Flip-Flops

Heeled flip-flops aren't going anywhere this summer, so consider styling the trendy silhouette with cozy attire.

Comfortable Summer Outfit: Make Your One-Piece The Star Of Your Look

If you're spending an afternoon in the sun, ditch the pants and finish off your one-piece with a white blouse tied around you.

Comfortable Summer Outfit: Layer Your Jewelry

Throw some delicate jewels into the mix to make your casual look appear a bit more put-together.

Comfortable Summer Outfit: Test Drive A Fresh Animal Print

Cow print has arguably replaced leopard, so if you haven't yet tried out the print, make May the month you do so.