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12 Trendy Boxer Shorts Outfit Ideas

This post discusses 12 trendy boxer shorts outfit ideas.

Hey fashionistas! Today, I’m super excited to share one of my most recent favorite style pieces with you – boxer shorts outfits.

If you’re like me, you likely are a bit unsure if the boxer short trend is for you or you may wonder why in the world it’s even a popular trend.

If you love a mix of comfort and chic, you’re in for a treat. Whether you’re lounging at home, hitting the beach, or running errands around the city, boxer shorts can be your go-to for effortless style.

And when styled correctly, the once only for men boxer shorts, can actually become one of your favorites!

In this post, I’ll be sharing some of my favorite boxer shorts outfit ideas that are perfect for any occasion. From casual daywear to unexpected evening looks, there are endless possibilities of boxer shorts outfits!

This post contains affiliate links from which I may make commission at no extra cost to you. Read full disclosure here.

How to Style Boxer Shorts

Lightweight Vest Top and Sneakers

Boxer shorts and a lightweight vest top make for an effortlessly cool and breezy outfit.

Choose a vest top in soft, breathable fabrics like cotton or linen, which pair perfectly with the relaxed fit of boxer shorts.

You can also stick with neutral or pastel shades for a summery vibe, and complete the look with a pair of classic Samba sneakers.

This combination is perfect for a casual day out, whether you’re grabbing coffee or taking a stroll in the park. To add a bit of personality, accessorize with a simple necklace and/or a baseball cap.

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Denim Vest Top and Boots

For a look that’s both stylish and edgy, pair your boxer shorts with a denim vest top.

The structured nature of denim contrasts nicely with the relaxed fit of the shorts, creating a balanced outfit.

Add your favorite cowgirl boots for the perfect casual concert outfit! To complete the ensemble, consider adding a purse in a fun color or a chunky bracelet to bring the whole look together.

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Oversized T-Shirt and Sneakers

An oversized t-shirt and boxer shorts combo is the ultimate in laid-back fashion.

Choose a t-shirt with a fun graphic or slogan to add some personality to your outfit.

The loose fit of the t-shirt paired with the boxer shorts creates a relaxed silhouette that’s perfect for lazy weekends or casual outings. Throw on a pair of comfortable sneakers to keep the look cohesive and practical.

You can also roll up the sleeves of the t-shirt for a more styled look, and add a crossbody bag to keep your essentials handy while keeping the casual vibe.

Tank Top with an Oversized Button Down Top

Layering is key to creating dynamic outfits, and pairing a simple tank top with an oversized button-down shirt can transform your boxer shorts look.

Choose a tank top in a solid color and layer it under a button-down in a complementary shade or pattern. Leave the button-down open for a relaxed feel or tie it at the waist for a more fitted look.

This outfit is perfect for transitioning from day to night, and can be paired with either sneakers or sandals depending on the occasion.

You can style with some layered necklaces or a wide-brim hat for an extra touch of style.

Shop similar boxer shorts here.

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Chambray Button Down Top and Birkenstock Clogs

A chambray button-down top is a versatile piece that pairs wonderfully with boxer shorts.

Roll up the sleeves for a relaxed look, and leave a few buttons undone at the top for a breezy feel.

Pair this outfit with Birkenstock clogs for a comfortable yet stylish finish.

This outfit is great for a casual brunch or a day of shopping, and you can easily accessorize with a simple leather tote or a rattan bag for more coastal vibes, and some sunglasses to complete the look.

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Cropped Graphic T-Shirt and Sneakers

Inject some fun into your wardrobe with a cropped graphic t-shirt and boxer shorts. The cropped length of the t-shirt helps to balance the loose fit of the shorts, creating a flattering silhouette.

This outfit is perfect for festivals, outdoor activities, or casual outings. To enhance the look, consider adding a denim jacket or a colorful backpack, which can also provide some extra storage for your essentials.

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Cropped Graphic Tee and Boots

For a bold and edgy look, pair your boxer shorts with a cropped graphic tee and a pair of stylish boots. This combination is perfect for making a statement, whether you’re heading to a concert or just want to stand out in your everyday style.

Complete the look with a fun cardigan or a leather jacket for an edgy touch and a chunky necklace to really make it pop.

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Oversized Sweatshirt and Sandals

An oversized sweatshirt with boxer shorts is the ultimate in cozy, casual wear.

Choose a sweatshirt in a soft, comfortable fabric and a color that complements your shorts. The oversized fit adds a relaxed vibe, making it perfect for lazy or casual days.

Pair this with some comfortable sandals for an effortlessly stylish look. This outfit is ideal for transitional weather when you want to stay cozy but not too warm.

Accessorize with a simple crossbody bag and some minimalist jewelry to keep the look clean and chic.

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Sweatshirt and Sneakers

For a sporty and retro-inspired look, pair your boxer shorts with a classic sweatshirt and Samba sneakers. This combination is both comfortable and stylish, making it perfect for a day of errands or a casual outing.

Choose a sweatshirt in a bold color or with a vintage logo to add some character to your outfit. The Samba sneakers add a touch of retro flair and are incredibly comfortable for all-day wear.

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Hoodie and Sneakers

A hoodie and boxer shorts combo is perfect for those cooler days when you still want to keep it casual.

Pair it with your favorite sneakers for a look that’s both comfortable and stylish.

This outfit is great for running errands, lounging at home, or even a casual meetup with friends. You can also add a beanie or a backpack to complete the look and keep it practical.

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Blazer over a Graphic T-Shirt and Loafers

Elevate your boxer shorts by pairing them with a blazer over a graphic t-shirt. This unexpected combination brings a sophisticated twist to a casual outfit.

Choose a blazer in a neutral color to keep the look polished, and a graphic t-shirt that adds a bit of personality.

Pair with loafers to add a touch of elegance, making this outfit perfect for casual business meetings or stylish day outings.

Accessorize with a statement watch or a sleek handbag to complete the ensemble.

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Cardigan and Loafer Flats

For a cozy yet chic look, pair your boxer shorts with a cardigan and loafer flats.

Go for a lightweight cardigan for warmer days or a chunky knit for cooler weather. The cardigan adds a touch of sophistication while keeping the outfit comfortable.

Pair with loafer flats to maintain a polished appearance. This outfit is perfect for casual workdays or leisurely weekends.

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Shop the Looks

Incorporating boxer shorts into your wardrobe can create stylish and comfortable outfits for any occasion.

With these outfit ideas, I hope that you can confidently experiment and find looks that suit your style.

For more fashion inspiration and similar outfit ideas, be sure to check out our other posts on the blog. Happy styling!

Xoxo,

Diana Colibri

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