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How To Style Boxer Shorts (Plus A Bunch To Shop!)

  • June 16, 2025
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how to style boxer shorts

Boxer shorts came on the scene in a big way last summer, and at first, I was perplexed. I would never wear my pajamas in public! But as with most trends, these grew on me. Plus, I’m all for trends that are practical and comfortable for hot summer days with my kids. I purchased this pair of boxer shorts a few weeks ago, and I’m having fun styling them this summer. I know a few of you have also jumped on this trend, and I got a few requests for more styling ideas so I put together this post with eight outfit ideas. I kept these really simple using mostly pieces that I already have in my closet.

With a super casual short like this, your first instinct might be to pair them with casual tops and shoes, but I actually think these work best with dressier tops. It makes the overall look more balanced. You definitely can style them with your basic tees and tank (and I have some ideas for that below), but maybe instead try them with a nice linen top, a button down shirt, or even a feminine blouse. This creates tension in your outfit and makes for a more interesting look.

The boxer shorts I purchased are from Donnie. They are a bit pricey, but the quality is excellent and they wash well. Head to the bottom of this post to shop more boxer shorts at different price points (there’s a pair for everyone there.)


How To Style Boxer Shorts

With A Cropped Linen Top

how to style boxer shorts with a cropped linen tank, blue and white striped boxer shorts, mesh flats, a cream perforated tote bag, and cat eye sunglasses
Linen Top / Boxer Shorts / Mesh FLats / Tote Bag / Sunglasses

This look inspired me to add a cropped linen top to my summer wishlist (coming soon!) As I mentioned above, I like how this top is a bit more dressy and makes the boxer shorts look less like pajamas. The cropped length of the top is also nice because you don’t have to do any tucking which can get all weird and bunchy sometimes with an elastic waist bottom (not to mention sweaty.)


With A Blouse

boxer shorts outfit with a white blouse, brown flip flops, brown woven bag, and tortoiseshell sunglasses
Top / Boxer Shorts / Sandals / Bag / sunglasses

I haven’t tried this combo yet, but I’m definitely going to! There is no shortage of white blouses to shop right now, and there is something about pairing it with a casual short like this that makes for a really cute look. I went with some easy sandals and a woven bag for accessories.


With A Button Up Shirt

boxer shorts outfit with a brown linen button down, brown sandals, brown sling bag, and tortoiseshell sunglasses
shirt / boxer shorts / sandals / bag (ASHLEYR15 for 15% off) / sunglasses

This is one of my favorite ways to style boxer shorts. I recommend wearing the shirt untucked (you can do it! trust!) for an breezy summer outfit. I picked a brown shirt, but I think it would look equally good with white and black. Go with a linen or cotton poplin button down for the summertime.


With A Sweater Tee Or Tank

how to style boxer shorts with a brown sweater tank, white and blue striped boxer shorts, brown sandals, a brown woven tote bag, and tortoiseshell sunglasses
tank (tee version here, ASHLEY20 for 20% off) / boxer shorts / sandals / bag / sunglasses

Swapping a sweater tank with some texture for a regular basic tank elevates this casual look. You could also try a sweater tee instead of a tank (see this look I wore a few days ago.) I added some casual sandals (these are on my wishlist), a basket bag, and some cat eye sunglasses.


With A Sweater Or Cardigan

how to style boxer shorts with a black cardigan, blue and white striped boxer shorts, black strappy sandals, and a tan woven tote bag
cardigan / boxer shorts / sandals / bag / sunglasses

If you live somewhere with a cooler climate, try pairing your boxer shorts with a sweater or cardigan. I actually wore this look recently as well. If it’s hot where you live, you could wear the sweater over your shoulders or tied around the waist. You may need it when you go indoors.


With A Waistcoat

boxer shorts outfit with a black waistcoat, brown and white striped boxer shorts, black strappy sandals, a black rope tote bag, and cat eye sunglasses
waistcoat (similar) / boxer shorts / mesh flats / bag / sunglasses

Styling a waistcoat with your boxer shorts may seem odd at first, but I think the look is super stylish and trendy. Just try it! I finished the look with some mesh flats, a rope bag, and sunglasses. I’ll be wearing this outfit very soon!


With A Tank

boxer shorts outfit with a blank tank, blue and white striped boxer shorts, black strappy sandals, silver hoop earrings, a tan straw tote bag, and cat eye sunglasses
tank / boxer shorts / sandals / bag / earrings (ASHLEYROHR10 for 10% off) / sunglasses

If you do plan to wear your boxer shorts with more casual tops like tees and tanks (I will be!), make sure you style the whole look. Do your hair, add a little makeup, put on some jewelry, and a nicer shoe. It’s all about balance.


With A Tee & Sweater Over The Shoulders

how to style boxer shorts with a white tee, navy sweater worn over the shoulders, low profile sneakers, a black rope tote bag, and black cat eye sunglasses
tee / sweater / boxer shorts / SNEAKERS / socks / bag / sunglasses

I’ve seen boxer shorts styled this way all over Pinterest so I had to include it! To make this combo of a tee and boxer shorts not look like pajamas, add a sweater over the shoulders, some cute crew socks, low profile sneakers, and a summery bag.


Shop Boxer Shorts

Read More:
Eight Outfits With White Jeans
How To Style A White Poplin Skirt

This blog post contains affiliate links. When you shop my links, I make a small commission at no cost to you. This is how I earn an income to support my family. Thank you!

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