Boxer shorts are making a major fashion comeback! These loose-fitting shorts are breathable, comfy, and bring a vintage vibe that’s totally on-trend right now.
Ready to rock the boxer shorts trend but unsure how to style them? Look no further! This post has 20 effortlessly cute outfit ideas perfect for casual wear.
1. Crop Top and Leather Jacket
This first outfit pairs classic black boxer shorts with a matching black crop top. Adding an edgy black leather jacket contrasted with clean white sneakers keeps things interesting.
This is a great go-to look when you want something easy to throw on that’s still eye-catching.
2. Cropped Button-Up and Corset Top
Take your boxer shorts from day to night with this outfit featuring a cropped white button-up shirt layered over an orange corset top.
White sneakers keep things casual, while the floral shorts add a feminine touch. This fun look is perfect for weekend brunches or a night out with friends.
3. Button-Up Cardigan and Striped Shorts
For breezy spring and summer days, you can’t go wrong with this relaxed outfit. A cozy white button-up cardigan pairs nicely with cute mint green striped boxer shorts.
It’s a breathable and easy look for running errands or meeting friends for an iced coffee date.
4. Oversized Sweater and Gingham Shorts
Oversized sweaters are a wardrobe staple, and they pair perfectly with boxer shorts. This cream sweater has a slouchy, relaxed vibe that contrasts nicely with tailored green gingham boxer shorts.
Finished off with crew socks and beige sneakers, it’s a comfy casual look for weekends or travel days.
5. Button-Up Vest and Pinstripes
Elevate your boxer shorts with this sophisticated outfit featuring a light gray button-up vest. Navy pinstripe shorts lend a polished look, while white ankle boots tie everything together.
It’s a great transitional outfit that works for the office or evenings out.
6. Gingham and Clogs
This laidback look features a classic white tee paired with bright blue gingham boxer shorts.
White crew socks and comfortable Birkenstock clogs finish off this relaxed weekend outfit. It’s perfect for running errands or casual weekend activities.
7. Graphic Tee and High-Tops
A graphic tee always lends a playful, youthful vibe to any outfit. Paired with vibrant red gingham boxer shorts and crisp white high-top sneakers, this fun look will turn heads for all the right reasons.
It works great for casual days or weekend activities.
8. Cropped Top, Gingham, and Blazer
This outfit proves that boxer shorts can also look dressy and pulled together.
A white cropped tank top and red gingham shorts form a nice color pairing, while a black oversized blazer and cowboy boots add polish.
It’s a great going-out look that’s still comfortable.
9. Button-Up and Striped Shorts
This outfit features a crisp white short-sleeve button-up blouse tucked into light blue striped shorts, paired with black sandals. It’s a breezy, put-together look that’s perfect for warm weather.
10. Cropped Top, Cardigan, and Gingham
Here’s another way to wear gingham boxer shorts—with a cropped white tank, brown button-up sweater, and beige sneakers.
The cropped top and sneakers add casual flair, while the cardigan makes this a look suitable for running errands or meeting up with friends.
11. Sleeveless Top, Blazer, and Cowboy Boots
Who says you can’t wear shorts in cooler weather? This outfit features a white sleeveless bodysuit tucked into crisp white high-waisted shorts, with a black oversized blazer adding warmth and polish. Black cowboy boots finish everything off.
12. Bodysuit, Striped Shorts, and Flats
This outfit features a few trends—a red sleeveless bodysuit, blue striped boxer shorts, an oversized navy blazer, and bright red Mary Jane flats.
Put together, it makes for a stylish day-to-night look that’s ultra-comfortable but still eye-catching.
13. Oversized Denim and Sneakers
You can’t go wrong pairing oversized denim with boxer shorts. This outfit features a graphic tee, blue striped shorts, a loose denim jacket, and white sneakers.
It’s a great weekend look that’s effortlessly cool. The oversized pieces contrast nicely with the fitted tee and shorts.
14. Bralette Top and Button-Up
Stay cool on hot summer days with this breezy outfit. A white bralette top and light blue shorts make the perfect pairing, while an unbuttoned light blue button-up shirt adds a relaxed layer.
Black flip flops finish off this laidback summertime look.
15. Polo and Headband
Polo shirts can look dressy or casual depending on how they’re styled. Here, a crisp white polo matches nicely with white boxer shorts.
Adding a coordinating white headband gives off relaxed country club vibes. It’s perfect for a casual summer boat cruise or garden party.
16. Cropped Tank and Ankle Boots
Cropped tank tops are ideal for showing off high-waisted boxer shorts. This outfit features a cropped white tank tucked into light blue striped shorts, plus a pair of edgy black ankle boots.
Black sunglasses add extra flair. It’s cute and casual but can also work for nights out.
17. V-Neck Sweater and Flip Flops
This simple yet stylish look features a black v-neck sweater paired with bright blue striped boxer shorts and black flip flops.
It’s a great outfit for transitional weather, when you want light layers along with the comfort of shorts. The relaxed vibe makes it perfect for casual days.
18. Layered Button-Ups and Sandals
Stay breezy in the summer heat by layering light button-up shirts over your boxer shorts.
Here, a gray tank top and pink striped shorts peek out from underneath an unbuttoned light blue button-up and tan sandals.
It’s a relaxed layered look perfect for warm-weather activities.
19. Cropped Tank, Gingham, and Blazer
Gingham prints pair nicely with basic white tanks, as seen in this cute outfit.
A cropped white tank top matches the white blazer, while blue gingham boxer shorts and white sneakers tie everything together.
This fun look goes great from the office to happy hour.
20. Striped Shorts and Mary Janes
Finally, this last outfit shows another way to style classic striped boxer shorts—with a simple white tank tucked in to highlight the waist, along with a black blazer and Mary Jane shoes.
It’s pulled-together enough for work or a nice dinner out but still breathable and comfy.
