How to Style Shorts: 5 Cute Summer Outfit Ideas for Women

Hi loves! Let’s talk summer shorts outfits! Finding a pair of shorts that feels comfortable, flattering, and stylish can be a challenge, especially when you’re trying to figure out what tops and shoes to pair with them. But trust me, shorts can be SO versatile! Whether you love high-waisted shorts, flowy paperbag styles, or classic denim cutoffs, there are so many cute ways to style them for summer. Today, I’m sharing 5 ways to style shorts this summer, featuring affordable fashion finds, outfit inspiration, and my favorite styling tips. From casual everyday looks to dressier outfits with heels and ankle boots, these high-waisted shorts outfit ideas are perfect for brunch, date nights, vacations, and everything in between! Don’t forget to check out my Amazon Storefront for more affordable fashion, home decor, and everyday favorites.

How To Style Shorts This Summer

1. Style Gingham High-Waisted Shorts With a One-Shoulder Top

If you’re wondering how to style high-waisted shorts, one of my favorite tricks is pairing them with a fitted top to balance out the silhouette. I personally LOVE high-waisted shorts because they emphasize the waist and can be so flattering! I recently picked up these adorable gingham high-waisted shorts, which came in a set with three crop tops. The ruffled hem is such a fun detail, and I love how the shorts flare out at the bottom for a flowy, feminine look. For this outfit, I paired them with a white one-shoulder crop top, my favorite white booties, and a cream fedora. You can also shop a more affordable fedora option here. These gingham shorts would also look SO cute with a simple bodysuit, fitted tank top, or lightweight cardigan. Such an easy outfit for summer brunch or a weekend outing!

2. Pair Black High-Waisted Shorts With a Hot Pink Wrap Top

If you’re a little hesitant about wearing shorts, black high-waisted shorts are such a great place to start! I love how versatile they are, and they’re perfect for creating a more polished summer outfit. I purchased these black high-waisted shorts for around $14, and I’m obsessed with the belted waist! The belt adds such a cute detail while helping define the waistline. One important sizing tip: size up in these shorts, as I found they run small. To add a fun pop of color, I paired them with this gorgeous hot pink wrap top and my favorite white ankle boots. The top and boots fit true to size. I LOVE this combination for a summer date night, girls’ brunch, or any occasion when you want to look a little more dressed up.

3. Style Flowy Paperbag Shorts With a Black Wrap Top

Girls, if you haven’t tried flowy paperbag shorts, you’re missing out! They’re one of my favorite alternatives to traditional fitted shorts because they have a relaxed, skirt-like silhouette that’s both comfortable and cute. I found these adorable paperbag shorts for around $12, and I LOVE the flared design. They almost look like a mini skirt, making them perfect if you prefer a little extra room through the legs. For this look, I paired them with a black wrap top, my favorite cream fedora, and white ankle booties. You can also grab a more affordable fedora option here. All the pieces I wore fit true to size.

4. Dress Up Black High-Waisted Shorts for Summer

One of the reasons I LOVE these black high-waisted shorts is how easy they are to dress up or down! A good pair of black shorts can be a summer wardrobe staple, especially when you’re looking for outfit combinations that feel a little more polished. I love the belted detail on this pair because it adds interest without needing a ton of accessories. When I originally purchased them, they were around $14, making them such an affordable find. Just remember to size up, since they run small. For a colorful, dressier combination, I love pairing these shorts with a hot pink wrap top and white boots. Both the top and boots fit true to size. You could also switch things up with a fitted bodysuit, lightweight blouse, or simple tank and add your favorite statement accessories. The best part about black shorts outfits is that you can easily change the entire look by swapping your top, shoes, and accessories!

5. Style Ripped Denim Shorts With a Peplum Top

Last but definitely not least, you can NEVER go wrong with a classic pair of ripped denim shorts! They’re such a versatile summer staple and can be styled with everything from basic tees and tank tops to dressier blouses. I love these distressed denim shorts because they’re easy to dress up or down depending on the occasion. For this outfit, I paired them with a cute peplum top, a black fedora, and my favorite white booties. Everything fit true to size. If you’re wondering what to wear with denim shorts, I love pairing them with a feminine top to balance out the casual, distressed look. You can also swap the ankle boots for sandals or sneakers for a more relaxed everyday summer outfit. For even more affordable warm-weather outfit inspiration, check out my summer Amazon fashion finds under $100.

Tips for Finding Flattering Summer Shorts

Finding shorts you feel confident and comfortable in can take a little trial and error, but there are SO many different styles to choose from! Here are a few of my favorite tips for shopping for and styling summer shorts.

• Try high-waisted styles. I personally love high-waisted shorts because they emphasize the waist and pair beautifully with cropped or tucked-in tops.
• Look for flowy silhouettes. Paperbag shorts and relaxed styles are great if you prefer more room through your hips and thighs.
• Pay attention to inseam length. Try a few different lengths to find what feels most comfortable for your proportions and personal style.
• Balance your outfit. Pair loose-fitting shorts with a more fitted top, or style fitted denim shorts with a flowy blouse.
• Have fun with accessories! A fedora, statement earrings, cute handbag, or fun pair of shoes can instantly elevate a simple shorts outfit.

And remember, the most flattering shorts are the ones YOU feel amazing wearing!