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What Should I Wear? Summer Style Edition

By: Caitlin Madden
Published: 6/17/25
Updated On: 6/5/26

Free People’s fashion hotline… who’s calling?

Do you ever wish you had an expert on-call for all of your fashion-related questions? Someone to help you find the perfect outfit every day? Someone who can basically shop for you? Well, that’s kind of what it’s like working at Free People.

Everyone is constantly talking about the latest trends, the next big style, the must-have items—there’s underlying fashion advice in every conversation. I often find myself taking these little nuggets of FP wisdom and working them into my own wardrobe choices.

So now, I’m letting you be part of the conversation.

I took some of the most asked fashion questions, consulted our very stylish Home Office employees, and rounded up our most-recommended products for each situation.

First up: outfit ideasn to wear this summer. Because there’s nothing like dusting off last year’s summer wardrobe and realizing you need to do a little refresh.

Come on, let’s go shopping together.

Genevieve Midi Dress

A PACKABLE SUMMER DRESS THAT WON’T WRINKLE IN MY SUITCASE

“Help. I’m going on vacation and I have some things planned that I want to dress up for, but I don’t want to waste time ironing.”

Allow us to introduce our most coveted packables ala free-est. These knit sundress styles are made with airy linen and cotton (THAT ARE ALREADY PURPOSEFULLY CRINKLED); plus the woven designs are so beachy, they’re practically begging to be added to your summer packing list.

Explore Sundresses

A BAG TO TAKE FROM WORK TO HAPPY HOUR

“I’m trying to make the most of summer by saying yes to plans right after work, so I need a bag that can fit my laptop, my makeup bag and some day-to-night essentials."

Our Emerson tote bag fits everything and then some. The oversized, slouchy style is big enough to stash your work life, with space left over to hold whatever you need to be going-out-ready (you could probably fit a whole change of clothes in here!). Plus, it’s crafted in a stunning leather that comes in lots of colors to choose from.

Explore Tote Bags

We The Free Emerson Tote Bag

Sugar Rush Jelly Sandals

A SHOE THAT GOES WITH EVERY SUMMER OUTFIT

“There is nothing harder than finding summer shoes. I feel like I need to buy a different pair for everything I wear, but I can’t do that so I need to find something that’s actually versatile and works with all my summer outfits.”

These sandals scream summer and FUN, making them the perfect shoe to style with all your summer outfits. They’re minimal and on-trend. They’re cool enough to pair with shorts and a tee, but could easily be dressed up with a flowy maxi or some fun flares.

Explore Sandals

SHORTS THAT AREN’T TOO SHORT OR TOO LONG

“I dread shorts season. I feel like every pair I find is either more revealing than I’d like or too long and looks a little sloppy. I need to find something that’s more flattering in between.”

You’re in luck because mid-to-long shorts are the summer’s biggest trend for bottoms. These mid-length shorts are a cutoff version of our favorite slouchy jeans, giving you opportunity to breathe while keeping that easy, relaxed silhouette that looks effortlessly cool.

Explore Mid-Length Shorts

We The Free Tippi Denim Shorts

Charlie Lace Microfiber V-Neck Bralette

A BRALETTE THAT’S COMFY AND LIGHTWEIGHT

“Wearing a bra in the summer can be a nightmare–I’m sweaty, constricted and so uncomfortable. I need something breathable and soft instead.”

Keep it simple with this soft bralette in a soft and stretchy microfiber jersey fabrication. It offers lightweight support with an easy pull on style and comfortable stretch that won’t squish you or trap in heat when it’s already hot outside.

Explore Bralettes

BIKINI BOTTOMS THAT ARE FAMILY-VACATION-APPROVED

“I’m headed on a family beach trip and I want a swimsuit that gives me a little more coverage than my typical cheeky styles.”

These shortie-style bottoms give the perfect moderate coverage while still offering a flattering, low-rise fit. They’re a boyshort-inspired silhouette that’ll keep you comfortable whether you’re playing beach games, splashing in the waves, or laying in the sun.

Explore Full Coverage Swim

free-est Dixie Swim Shortie

Shop Summer Vacation Outfit Ideas

Frequently Asked Questions on Summer Styling

What should I pack for a summer vacation that won't wrinkle?

We love our airy knit styles for travel—many of our free-est styles are crafted in crinkled cotton; plus, the woven designs feel perfectly beachy and vacation-ready.

What bag works for the office and after-work summer plans?

Look for an oversized, slouchy tote that can fit your laptop, makeup bag, and day-to-night essentials. Our leather totes are roomy enough to hold everything you need to transition from desk to happy hour without missing a beat. Best of all, it’s the perfect accessory to wear with all your summer outfits.

What sandals go with every summer outfit?

Sandals come in sooo many shapes and sizes that it’s hard to pin down just one style. This season we’re really loving jellies–because they’re on-trend but fun enough for seasons forward, and they pair just as easily with shorts and a tee as they do with a flowy maxi or fun flares.

How do I find flattering summer shorts that aren't too short or too long?

Mid-length denim shorts in a slouchy silhouette hit that sweet spot—they offer more coverage without looking sloppy, and they keep that easy, relaxed vibe that feels effortlessly cool.

What's the most comfortable bra to wear in hot weather?

A soft, stretchy bralette is your best friend in summer. It offers lightweight support without constricting you or trapping heat, so you stay comfortable even when temps hit sweltering. A light, breathable bralette is the perfect base for all of your best summer outfits.

What swimsuit bottoms offer more coverage for family trips?

Shortie-style bikini bottoms give you moderate coverage with a flattering, low-rise fit. The boyshort-inspired silhouette keeps you comfortable all summer long, whether you're playing beach games or lounging in the sun.

MORE, PLEASE!