What to Wear on the Weekend

Date: May 15, 2024

Ah, the weekend! There’s nothing like a summer Saturday and Sunday; the sun is shining, you’re feeling relaxed (we hope!) and you’ve got two full days to hang out with friends and family, get some work done around the house and enjoy a little time to yourself. While one of the best things about the weekend is that you can ditch your office clothes and chill in your favorite old sweat shorts or sundress, you probably have some to-dos on your agenda that require a little more effort.

A woman with short blonde hair is wearing a white sleeveless hoodie, light blue jeans, and white sandals. She stands by a large window in an indoor setting with a colorful striped bag strap across her body. This look is a great example of casual outfits, perfect for what to wear on the weekend.

Trendsend’s Weekend Chic theme box takes all the guesswork out of casual weekend dressing; as always, our custom clothing boxes are packed with easy (and cute!) pieces that can be mixed and matched for a variety of occasions. Level up your weekend game and get dressed with us — and never wonder what to wear on the weekend again!

What to Wear for Weekend Errands

You want to look cute, but not overdressed or fussy; you want to be comfortable, but not sloppy. Who knows who you’ll run into at the grocery store or coffee shop? Give your leggings and athleisure the summer off and have a little fun with casual outfits for the weekend.

We always recommend a great pair of denim shorts or boyfriend jeans as a weekend staple, because they go with everything, can be dressed up or down, and have multiple pockets to stash farmers market cash, lip balm, and your keys and phone. The easiest summer errands uniform is a vintage-inspired band tee, cutoffs, a belt bag and sandals. Done and done!

If you’re on Team Dress versus Team Shorts, a lightweight, breezy midi or minidress in a solid color or versatile print like a classic stripe will never steer you wrong. It’s great with sandals and sneakers, and you can play with proportions by tying a thin knit sweater around your waist too. We love a great dress paired with a chic tote and sandal for a day that starts with brunch and ends with an impromptu backyard BBQ.

A woman with long dark hair is wearing a blue sleeveless dress and tan flip-flops. She is holding a woven straw handbag and is smiling. This outfit is ideal for what to wear on the weekend, showcasing casual outfits and comfortable style.

A wide leg or straight leg jean gives you the easygoing comfort you crave on Saturday and Sunday while still looking pulled together. For a more laid-back look, opt for light wash denim versus dark and style with loafers or slides. Add a fitted tank, a jacket or sweater, a baseball cap, and sunglasses, and you’re good to go.

What to Wear to Kids’ Activities and Games

Weekend Chic - A collage of various casual outfits including a white t-shirt with green and blue stripes, a blue sleeveless dress, a white t-shirt, a lime green knit sleeveless top, a pair of distressed jean shorts, a denim skirt, a gold necklace, and a pair of silver hoop earrings. These items are perfect for what to wear on the weekend.

Soccer, T-ball, a neighborhood kickball game … whatever your kids are playing, you’re probably sitting on the sidelines cheering them on. Games aren’t just a chance for your kids to flex their athletic skills and practice teamwork and sportsmanship — they’re a social event for parents! Think practical, easy, relaxed pieces for hanging out in a camp chair or on a blanket, like a midi tank dress and denim or twill utility jacket for an evening game, or a hat and sunglasses (and lots of SPF!) for a mid-day tournament. A belt bag gives you the option to go hands-free, and a cute oversized tote is great for stashing snacks, water bottles, and tablets, plus a blanket and book for you.

Birthday parties tend to be more active, so you probably don’t want to fuss with a short dress if you’re jumping on trampolines or supervising a bunch of little swimmers. This is a great time to pull on those longer-length jean shorts, a baseball cap, and a rocker tee; a game of kickball or tag may be just around the corner, so don’t forget your sneakers!

What to Wear to a Baby Shower, Bridal Shower, or Brunch

The weekends aren’t just about chilling; chances are you probably have a brunch with friends or family, a baby shower, or a bridal shower on the calendar too. A colorful printed sundress is always a safe bet for more “fancy casual” events, and white pants or jeans always bring the spring and summer vibes, especially with a metallic sandal, heeled clog, or platform slide.

A woman with short blonde hair is wearing a white tank top with a blue floral print and light blue jeans. She is sitting at an outdoor café table with wicker chairs, wearing metallic sandals. This casual outfit is ideal for what to wear on the weekend.

To keep your weekend looks as fun and fresh as your plans, try one of Trendsend’s theme boxes, like the aptly-named Weekend Chic Box, which is packed with versatile casual pieces that allow you to kick back, relax, and enjoy every second of Saturday and Sunday — and that’s what it’s all about, right?