6 Incredibly Cute Boxer Shorts to Steal from the Boys

I’ve already waxed on about how much I love pajamas (and, don’t worry, I still do), but one of my other favorite items of clothing for sleeping and lounging is a pair of boxer shorts. They may be frequently made for men/boys, but that’s no reason I shouldn’t be able to wear them to my heart’s content. I called this a post of “incredibly cute” boxers because they border on saccharine– but I am unapologetic. You’ll have to wait until next time I make a boxer list for anything dashing or sexy. Enjoy these fun boxers :)

Max Holliday Mimi Boxer Shorts £35

Max Holliday Mimi Boxer Shorts £35

I may love the new Max Holliday collection nearly as much as my already well documented love of Mimi Holliday. I have to say, the gorgeous silk lining on the waistband as well as the sweet white polka dots have me swooning over these.

Santa Girls Boxers, $18.50

Why is it that when I think of these boxers on a guy it seems like it would be a little odd– and yet on a girl it seems adorable (it might be because I’m gay?). I have to say, I think tiny Santa Pin-Ups all over my boxers would be fabulous.

Turnbull & Asser Gingham Check Cotton Boxer Shorts $95

Yes, these boxer shorts are absurdly expensive ($95!), but they are also incredibly cute. I’m a sucker for pink gingham, what can I say. At least I could say that they are very classy.

Gap Kisses Boxers, $12.50

Love these lipstick kiss boxers— again, a little odd if you took off a guy or girl’s pants and you found these (not that they’re too girly… just, unironic lipstick kisses on your nether regions seems a little, well, presumptuous)– but perfect to wear to bed or lounging about the house. I think the fact that the lipstick marks are natural and a bit smudgy makes them even nicer.

Burberry Check Print Woven Boxers, $50

When are red Burberry boxer shorts a bad idea? I think the answer is never. I am not the biggest fan of Burberry plaid at all times, but I am a fan of plaid when it comes to boxers, so they are a perfect fit.

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Max Holliday Emma Boxer Shorts £35

Okay, yes, it’s another pair of Max Holliday boxers, but I couldn’t help myself! Look at that beautiful lining and tell me you’ve seen a cuter pair of boxer shorts. (It can’t be done).

Do you like boxers as sleepwear? Do you think these are cute or just silly?

If you liked this post, you might also want to read these:

‘Lingerie’ for Men? When White Boxers Don’t Cut It

Lingerie Androgyny: When Lingerie Doesn’t Mean Femininity

Trend of the Week: Pyjama Party

14 Comments
  1. I’m delighted you’re challenging traditional dress code boundaries, and also glad to see that men’s clothing designers are not afraid to offer underwear in colors and designs that may be deemed as “feminine”.
    I hope the shift in tolerance and acceptance of the last few decades towards women wearing clothing styles regarded in the past as strictly masculine will also go the other way around with acceptance of more diverse men’s styles, fabrics, etc.

    I often chuckle upon seeing women’s clothing items labeled something like “the boyfriend’s cardigan”. Who knows, maybe one day there will be a men’s line known as “the girlfriend’s lingerie”.

    • the girlfriends lingerie line would be great. I would be first in line. (as long as there is a cutr pushup bra in there)

  2. I was looking/lusting after these after you mentioned them on Twitter… they look so cute and comfy! I pretty much want all of them… I find boxers really comfy for loungewear :) And I don’t think they cross the line of being “too feminine” for men, either.

  3. These are super cute (particularly the last one!), but I prefer boxer briefs to boxers, since I wear them as underwear AND shorts (and also because they are super comfy). Amusingly, given my wardrobe, I can only wear my boxer briefs under long, flowing skirts (boxer briefs + leggings = disaster).

  4. I’va had my eyes on a pair of Max Holliday boxers for ages. Anything with a bit of silk has my vote! Everyone needs a pair of silk underthings, regardless of gender and other such trivialities..

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  6. Caaaan I have one of each? Haha, I love boxers. I have two pairs of Pajama boxers currently, but they’re not the best fit or the comfiest. I’d love to replace them sometime.

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