Mom Fashion

How to Style Boxer Shorts and Pants Without Looking Like You’re Wearing Pajamas

written by EMILEE JANITZ

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boxer shorts outfits"
boxer shorts outfits

As a mom of two (soon to be three), I always appreciate when a fashion trend hits on both style and comfort. I want clothes to look cute and also be practical for everyday life. These qualities are especially important during the summer, when the temps are on the rise and many of us are experiencing our busiest season of the year.

Between some much-needed time out of office, May through August is typically chock-full. End-of-school events, summer camps and workshops, rotating sports schedules, and late nights full of bonfires and fireworks quickly pack the calendar. Again, style is greatly appreciated, and comfort is key. This summer, I’m personally so excited to see a mom-friendly fashion trend making its return: boxer shorts.

Why boxers are the perfect summer shorts for moms

At first, I’ll admit, I was skeptical. When boxer shorts first started circulating on fashion blogs and social media, I shrugged them off as something that looked good in aesthetic photos but not something everyday women would be reaching for as part of their out-of-the-house outfitting rotation. But skeptical doesn’t mean close-minded—and I’ve come to change my tune.

Last summer, I acquired a handful of boxer shorts and ended up wearing them on repeat. From festive summer holiday fits to ocean-side ensembles, these shorts very quickly began replacing my typical go-to jean shorts. And at six months pregnant, I’m pretty ecstatic that these shorts are still quite trendy. In fact, they’re gearing up to be even more popular than they were a year ago.

boxer shorts outfits emilee janitz
Source: Emilee Janitz

Boxer shorts and pants outfits to try this summer

Despite their laid-back appeal (or maybe because of it), styling boxer shorts and pants can seem daunting. I know what you’re thinking: Really? So, I can wear these pajama-esque shorts outside the house, and I’ll actually be cool for doing so? I know—it’s almost too good to be true. 

Or maybe you’re already on board with this trend but are looking for ways to shake up your typical styling. Here are some outfit ideas for pulling off your favorite (or soon-to-be acquired!) pair of boxer shorts and pants.

With Boots and a Pullover Sweater

There is no outfit combo I love more than a long-sleeve top and short bottoms. During breezy summer days or cool evenings, this translates to a seasonal sweater and a pair of favorite shorts. Retro-inspired boot silhouettes are continuing to skyrocket in popularity and go well with this dynamic duo. Bonus: They also protect your ankles from pesky insects. A basket bag adds yet another layer of practical cool.

american flag sweater and blue shorts

Shop this look:

  1. Boxers | Similar style
  2. Boots 
  3. Sweater
  4. Basket bag
  5. Sunglasses
boxer shorts outfits emilee janitz
Source: Emilee Janitz

With a Graphic Tee and Cowboy Boots

On a hot summer day, boxer shorts and an oversized tee are both simple and satisfying. While it may not be your first instinct, cowboy boots can add some intention to the look (more on-trend, less rolled-out-of-bed) and are sure to gain you a compliment or two—trust me!

graphic tee and blue shorts

Shop this look:

  1. Boxers 
  2. Graphic Tee
  3. Cowboy boots
  4. Sunglasses
  5. Tote bag

With a Vest and Chic Sunnies

Contrast is an easy way to add interest to any outfit. Style your laid-back boxer shorts or pants with a structured vest top for a visually appealing juxtaposition. Jelly flats and a crochet bag add even more texture to the look.

linen vest and striped pants

Shop this look:

  1. Boxer pants | Similar pants
  2. White vest 
  3. Sunglasses 
  4. Jelly flats 
  5. Bag

With a Bathing Suit

Both boxer shorts and boxer pants make phenomenal beach cover-ups. Pair them with your favorite suit and sandals and grab a trending beach read.

swimsuit and pink boxer shorts

Shop this look:

  1. Bathing suit
  2. Boxer shorts
  3. Bucket hat 
  4. Flip flops
  5. Sea charm necklace 
  6. Beach bag

With a Coordinating Top

Long live the days of matching sets! Truly, I hope they never go out of style. If you’re a fellow fan, rejoice knowing there are many boxer options sold alongside a coordinating top.

boxer shorts graphics

Shop this look:

  1. Boxer shorts 
  2. Button-up shirt
  3. Tank
  4. Sandals
  5. Beaded bag
boxer shorts outfits emilee janitz
Source: Emilee Janitz

With a Cardigan and Boat Shoes

My fellow coastal grandmas will be happy to hear that boat shoes are also currently surging in popularity (thank you, fisherman aesthetic!). Pearls and a chic cardigan dress up boxer shorts for a window-shopping stroll through town or lunch by the water.

boxer shorts graphics

Shop this look:

  1. Boxers
  2. Cardigan
  3. Boat shoes
  4. Bag 
  5. Necklace

With a Puff-Sleeve Blouse

With the right accompanying pieces, boxers can also be incredibly romantic and feminine. Try styling your favorite boxer pants or shorts with a puff-sleeve top and flats. A claw clip and beaded bag take the outfit up a notch.

boxer shorts graphics

Shop this look:

  1. Puff-sleeve blouse 
  2. Boxer pants
  3. Mesh flats
  4. Claw clip
  5. Bag

More of our favorite boxer shorts and pants

Boxer Pants

High-Waisted Seersucker Pant
American Eagle
High-Waisted Seersucker Pant

2 colors available
sizes XXS – XXL

Shop now
The Wren Boxer Pants
Anthropologie
The Wren Boxer Pants

9 colors and patterns available
sizes XXS – XL; 2 lengths

Shop now
Organic Cotton Poplin Wide-Leg Pants
Gap
Organic Cotton Poplin Wide-Leg Pants

2 colors available
sizes XXS – XXL; 3 lengths

Shop now
Cotton Boxer Pants
Amazon | LOMON
Cotton Boxer Pants

20+ colors and patterns available
sizes S – XXL

Shop now
Charleston Poplin Pant
Aritzia
Charleston Poplin Pant

3 colors and patterns available
sizes XXS – XL

Shop now
High-Waisted Poplin Super Wide-Leg Pants
Old Navy
High-Waisted Poplin Super Wide-Leg Pants

2 colors available
sizes XS – 4X; 3 lengths

Shop now
Mid Rise Pull-On Wide-Leg Pants
Gap Factory
Mid Rise Pull-On Wide-Leg Pants

2 colors available
sizes XS – XXL; 3 lengths

Shop now
Gingham Wide Leg Pants
Amazon | PEHMEA
Gingham Wide Leg Pants

4 colors available
sizes S – XL

Shop now

Boxer Shorts

Relaxed Pull-On Poplin Shorts
Gap Factory
Relaxed Pull-On Poplin Shorts

4 colors available
sizes XS – XXL

Shop now
Soft Rib Boxer
Aerie
Soft Rib Boxer

3 colors and patterns available
sizes XXS – XXL

Shop now
Gingham Scalloped Shorts
Lulus
Gingham Scalloped Shorts

2 colors available
sizes XS – XL

Shop now
The Wren Boxer Shorts
Anthropologie
The Wren Boxer Shorts

10+ colors and patterns available
sizes XXS – 3X

Shop now
Day to Day Solid Boxers
Free People | We The Free
Day to Day Solid Boxers

3 colors available
sizes XS – XL

Shop now
Out From Under Boxer Short
Urban Outfitters
Out From Under Boxer Short

8 colors and patterns available
sizes XS – XL

Shop now
Organic Cotton Poplin Boxer Shorts
Gap
Organic Cotton Poplin Boxer Shorts

4 colors available
sizes XXS – XXL; 3 lengths

Shop now
Curved Hem Pull-On Poplin Shorts
Madewell
Curved Hem Pull-On Poplin Shorts

sizes XXS – XXL

Shop now

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Emilee Janitz
ABOUT THE AUTHOR

Emilee Janitz, Contributing Writer

Emilee is an accomplished communications strategist and lifestyle journalist. She currently works on the content team at Enterprise SEO company Terakeet where she creates and executes reputation management strategies for Fortune 500 companies. She is a Contributing Fashion Writer for The Everygirl and has additionally been published on POPSUGAR, Motherly, MSN, and Yahoo.

Products included in graphics linked within article.