One of my favorite lazy-day secrets? Boxer shorts. Sometimes it’s just so nice to wear something breathable with a vintage vibe. But they can also be part of a super cute, put-together look!
Here are 20 outfit ideas to give you some inspiration.
1. Gingham and Clogs
This look is so laid-back. It starts with a classic white tee paired up with some bright blue gingham boxer shorts.
To finish it off, add white crew socks and a comfy pair of Birkenstock clogs. I really love this as a relaxed weekend outfit. It’s perfect for casual activities or just running errands.
2. Bralette Top and Button-Up
Need to stay cool on one of those super hot summer days? This breezy outfit is the answer.
I love the idea of a white bralette top with light blue shorts. It’s such a perfect pairing. Then, just throw on an unbuttoned light blue button-up shirt as a relaxed layer.
Black flip flops make this the ultimate laidback summertime look.
3. Button-Up Cardigan and Striped Shorts
For those breezy spring and summer days, you just can’t go wrong with this relaxed outfit. A cozy white button-up cardigan pairs so nicely with these cute mint green striped boxer shorts.
It’s a breathable and easy look. I think it’s perfect for running errands or meeting friends for an iced coffee date.
4. Striped Shorts and Mary Janes
Finally, here’s one more way to style classic striped boxer shorts. I’d start with a simple white tank and tuck it in to highlight the waist. Then, add a black blazer and some Mary Jane shoes.
It’s pulled-together enough for work or a nice dinner out but still breathable and so comfy.
5. Button-Up and Striped Shorts
This outfit is just so breezy and put-together. It features a crisp white short-sleeve button-up blouse that’s tucked into light blue striped shorts, paired right up with black sandals. It’s an ideal look for warm weather.
6. 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.
A black oversized blazer adds warmth and polish. Black cowboy boots finish everything off.
7. V-Neck Sweater and Flip Flops
This is such a simple yet stylish look. It features a black v-neck sweater paired with bright blue striped boxer shorts and black flip flops.
I think this is 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.
8. Oversized Sweater and Gingham Shorts
Oversized sweaters are a total 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.
9. Crop Top and Leather Jacket
This 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.
10. Oversized Denim and Sneakers
You really 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.
11. Cropped Tank, Gingham, and Blazer
Gingham prints pair so 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.
12. 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.
13. 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.
14. Cropped Button-Up and Corset Top
Take your boxer shorts from day to night with this outfit. It features 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.
15. 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.
16. 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.
17. Bodysuit, Striped Shorts, and Flats
This outfit features a few on-trend pieces. It has 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.
18. 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.
19. Cropped Top, Cardigan, and Gingham
Here’s another way to wear gingham boxer shorts. This one features a cropped white tank, a 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.
20. 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.