Summer Outfit Ideas: What To Wear From The Beach To The Street

As much as I love bold fashion, when it comes to shopping for the beach or pool, I tend to play it a bit safe. These days, I don’t go to the beach or pool nearly as often as I used to, so I’m more selective about the pieces I buy. I look for beach cover-ups and accessories that can work double duty—something I can easily wear on the street just as well as on the sand. After all, I’ll likely be wearing these pieces more around town than during the one or two times I’ll actually be poolside.

Maybe this mindset comes from having lived in Chicago for many years. If you’re not familiar, one of the best beaches—Oak Street Beach—is just off the Magnificent Mile and steps away from some of the best shopping in the city So whether you arrived by bus, subway, or on foot, you didn’t want to look “too beachy’ while walking down Michigan Avenue. You might be popping into a boutique, grabbing lunch with a friend, or even heading to the beach after work! 

Chic From The Beach To The Street

That’s what inspired this post. I want to show you how easy it is to put together a chic and functional outfit that takes you from the beach to the street—and looks appropriate at both. If you’re like me, you’ll probably end up wearing these pieces more on errands and casual days than you will poolside. The good news? That means you’re getting more mileage out of your wardrobe, which is always a win.

Beach-To-Street Check List

Here are a few of my favorite beach-to-street fashion essentials:

1. Swimsuit
Look for a comfortable swimsuit without a lot of embellishments or ties. A simple tank suit that fits like a bodysuit is ideal—it’s sleek enough to layer under other pieces and won’t scream “swimwear.”

2. Cover-Up
A long button-down shirt or shirt dress works beautifully. It provides coverage, style, and can double as a casual day dress or layering piece.

3. Beach or Tote Bag
Choose a nylon or canvas bag with a zip-top for security. This is one area where I say go bold—opt for bright colors or fun prints! It’ll still look great while shopping or grabbing lunch.

4. Slide Sandals
Supportive black pool slides with a sturdy rubber sole can go straight from sand to sidewalk. Bonus points if they’re waterproof and stylish.

5. Sun Hat
A sun hat with a smaller brim that fits securely is perfect. You want something that won’t fly away in the wind, especially if you’re walking city streets.

6. Sunglasses
Classic black shades in your favorite silhouette will serve you well at the beach and beyond. A timeless shape like aviators or oversized frames always works.

7. Cropped Jeans
Slip on a pair of your favorite cropped jeans over your suit. They’ll instantly elevate your look, and no one will even know you’re headed to the beach.

Beach To Street Style

Here is how to style it from the beach to the street. it’s so easy!

Beach Outfit

You’ll look chic on the beach at the pool with these beach essentials.

Shop The Beach Outfit Here:

Street Outfit

Simply tuck in your oversized shirt, slip on your favorite denim jeans and you’re ready for the city streets! 

Shop The Street Outfit Here:

And there you have it—an easy formula for going from beach to street in style. With just a few thoughtful pieces, you can head to the beach and still be ready to shop, grab a bite, or even meet friends for dinner afterward.  After all, summer fashion should be simple, stylish and functional—especially for women over 50. 

You may also like to read What to Wear On A City Break: A Chic Summer Vacation Capsule Wardrobe and The Classic Chambray Shirt Summer Outfit: How To Style It High-Low.

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