How I'm Styling Boxer Shorts: Best Outfits of 2025
If you want to hop on the easiest trend ever that all the cool girls are wearing for spring and summer, then you need a pair of boxer shorts! Yep, we are taking a literal pair of men's underwear and making it, cute? (Perhaps we're running out of ideas here in the fashion world.) But honestly, when a trend is comfy, you know I am on board to come up with outfit ideas for it!
So today I am sharing all the best boxer short outfits that will make you totally forget about that dingy, crumpled up pair of your boyfriend's sitting on the laundry room floor right now.
This trend popped up last summer, and I am excited for it's return because it's surprisingly chic and a fun way to add a pop of color to your spring and summer wardrobe.
And if you love this trend, be sure to check out the 16 other trends to know about for Spring here!
Chic & Easy Boxer Shorts Outfits To Rock This Season
So let's get into some new ways to rock boxer shorts that will make you feel fashion-forward but also comfortable! I came up with 9 different ways to style boxer shorts that I hope you absolutely love.
Pops of Green: Boxer Shorts with Cardigan and Denim Jacket
I think adding a pop of color is all the fun in styling up a pair of boxer shorts! I love this look I created that plays with layers and pulls in the green from shorts.
Related: 10 Insanely Cute Soccer Mom Outfits
Street Style Chic: Boxer Shorts with an Oversized Blazer
A classic pair of blue boxer shorts is the way to go if you want to invest in a pair that will work with any number of casual looks. I love this chic look when paired with an oversized blazer and plain white tee!
Related: 23 Chic Blazer Outfits for Women
Poolside Casual Look: Boxer Shorts as a Swim Cover Up
Boxer shorts are for sure a clothing item that is versatile and can totally be worn as a swim cover up. I love this look paired with a linen button-down shirt and bathing suit for a day at the pool, beach, or lake! I have worn this exact look all day on a boat and was so comfortable and felt so stylish!
Fall Transition: Boxer Shorts with an Oversized Sweater
I am loving taking the boxer shorts trend right into Fall and you can totally do this by pairing them with a trendy sweater and some Fall footwear like Birkenstock clogs with white socks. Add in a baseball cap for instant chic!
Related: Insanely Chic Ways to Style Birkenstock Clogs
Street Style Chic: Boxer Shorts with a Leather Jacket and Loafers
For cool girls only. (Yes of course I mean you!) I have loved seeing boxer shorts styled with leather jackets and loafers on my Pinterest feed, so I had to try styling up a pair just like the Pinterest girlies! If you love edgy looks, then this is for you.
Related: Cool Girl Tips on How to Style Loafers
Matchy-Matchy: Boxer Shorts with a Matching Button-Down Shirt
If you love a matching set moment like me, then this outfit is so chic! I have actually worn this exact look for a travel day, and it works so well because you can hop off the plane and right into vacation mode while staying comfortable. And the boxer shorts look so chic paired with a matching shirt.
Related: Exactly What to Wear on a Long Flight: Best Style Tips
Rainy Day Vibes: Boxer Shorts with Rain Boots
Another way to style these shorts up in the colder months when it's rainy! Perfect for a laid-back day when the weather is crappy. I love how they look paired with some rain boots and an oversized sweater.
Boxer Style Pants Look
So another micro trend that has popped up from the boxer shorts craze is boxer pants! They essentially are just pajama pants, with a boxer-esque elastic waistband and we are not mad about it! The perfect look for a casual day when it's not quite shorts weather.
Cherry Red: Boxer Shorts with Graphic Tee and Sneakers
Cherry red is the trend of the moment, so this last look I came up with features pops of red. Love this look with the red and white sneakers, red bag, and red baseball cap to tie in the red boxer shorts. It's the perfect summer outfit idea!
Are we loving the boxer shorts trend now? Feeling inspired to mix and match and come up with your own outfit ideas? Let me know your thoughts on this trend and which look was your favorite in the comments below!
Loved these outfits? Be sure to pin it for later:
