With some favoring the bold statement and others questioning their style, oversized shirts have sparked debates in the world of fashion. However, we cannot deny the fact that these shirts have a nostalgic comeback thanks to social media.
Oversized shirts with a bit of creativity and experimentation offer endless styling possibilities to wear all year, especially during summer. This wallet-friendly choice pairs with multiple pieces so that you create many different outfits for various occasions from professional environment to casual party.
The trend traced back in the 1920s to flapper style and then in the 1980s it encompassed the oversized shirts as a rebellion against fitted clothing. This attire again appeared on the canvas of trends in 1990s hip-hop culture.
It gained traction in 2010 when celebrities like Rihanna and Kanye West wore oversized outfits. Along with that, the comfort, inclusivity, body positivity, and stylish availability in all sizes made oversized clothing a popular wardrobe staple.
However, the beauty of these shirts is to wear them according to the moment to make a big difference in your overall look.
For instance, wear lightweight and breathable cotton, linen, or rayon fabrics for a beach day, casual outings, running errands, or when hanging out with friends and family. Likewise, if you are heading to a formal event or date night then choose oversized shirts with silk or satin and consider the weight and drape of the fabric.
There are numerous ways to style an oversized shirt and are worn by anyone regardless of body type. If you prefer a fitted look, add a piece of jewelry or belt to create a cinched waist. For a more polished look tuck in your oversized shirt in pants or dark skirts.
Many fashion icons have embraced the oversized shirt looks and if you want to recreate the same look. Ahead, see the best classic outfits to recreate now.
Outfit #1
Outfit is: Light blue oversized button-up shirt + White maxi skirt + Black heeled sandals + Black sunglasses
My note: Do you know those unbearably hot summer days when picking an outfit feels like a chore? Don’t worry. Keep it easy and go for a light blue oversized button-up shirt paired with a white maxi skirt, black heeled sandals, and a pair of black sunglasses.
Outfit #2
Outfit is: White button-up shirt + Gray crewneck T-shirt + Light blue denim cutoff shorts + Olive green sneakers with white socks + Oversized yellow-tinted sunglasses + Beige tote bag
My note: Looking for a laid-back yet versatile outfit that works from day to night? Consider the combo above. A white button-up shirt layered over a gray crewneck T-shirt, paired with light blue denim cutoff shorts and olive green sneakers, will keep you comfortable during the day and still look good as the evening cools down.
Outfit #3
Outfit is: Bright green oversized button-up shirt + Black mini skirt + Black knee-high boots + Orange quilted crossbody bag + Clear glasses
My note: Just because bright green isn’t the “trendy” color of the moment doesn’t mean it can’t be on point; take the outfit above as an example. The easiest way to make this color feel fresh is by choosing bold pieces like an oversized button-up shirt paired with a black mini skirt and knee-high boots for the perfect summer look.
Outfit #4
Outfit is: Blue striped oversized shirt + Beige mini skirt with red drawstring belt + Black ankle boots + Red patent leather shoulder bag + Gold necklaces
My note: Reminder: You don’t have to wear head-to-toe blue to make a statement with this color. Style a blue striped button-up shirt with your favorite beige mini skirt, black ankle boots, and a red patent leather shoulder bag. Do this, and you’ll capture that effortless vibe that’s always in style.
Outfit #5
Outfit is: White striped oversized button-up shirt + Light blue high-waisted jeans + White loafers + Beige handbag + Round sunglasses
My note: I have to admit that anything too casual usually doesn’t fit my idea of a put-together look, but the outfit above is an exception I didn’t see coming. Who would have thought that a simple white striped button-up shirt with light blue high-waisted jeans and white loafers could pull off such a look?
Outfit #6
Outfit is: Light blue striped oversized button-up shirt + White wide-leg pants + White tube top + Beige quilted handbag + Beige pointed-toe heels + Gold bracelets + Round sunglasses
My note: While it’s easy to wear the light blue striped button-up shirt on its own, consider trying something more creative like the outfit above. Layering it over a white tube top with white wide-leg pants and adding beige pointed-toe heels will give this classic shirt a fresh twist. Finish the look with a beige quilted handbag, gold bracelets, and round sunglasses for that extra touch.
Outfit #7
Outfit is: Blue striped button-up shirt + Black wide-leg pants + Burgundy oversized shoulder bag + Burgundy sandals + Black sunglasses
My note: If it’s not already obvious, let me emphasize: The secret to elevating any button-up shirt lies in the accessories. While it’s always good to keep up with seasonal trends, you can’t go wrong with timeless pieces—like a burgundy oversized shoulder bag, matching sandals, and black sunglasses.
Outfit #8
Outfit is: Red and white striped oversized button-up shirt + Light blue denim cutoff shorts + Black loafers with white socks + Straw shoulder bag + White oversized sunglasses
My note: While pairing a button-up shirt with standout accessories is a simple way to make it shine, it’s not the only way to create a memorable look. Take inspiration from the outfit above by styling a red and white striped oversized button-up shirt as a light layer over your light blue denim cutoff shorts.
Outfit #9
Outfit is: Light blue oversized button-up shirt + White pencil skirt + Black flip-flops + Black handbag + Black sunglasses + Gold earrings
My note: You don’t need bold prints to make this outfit stand out—just look at the ensemble above. By pairing a light blue button-up shirt with a white pencil skirt and black accessories, you’ll give this classic combo a fresh and updated feel.
Outfit #10
Outfit is: White oversized button-up shirt + White high-waisted shorts + Round sunglasses
My note: Want to take this classic piece from day to night? Try pairing a white button-up shirt with white high-waisted shorts and round sunglasses for a clean, effortless look that works for any occasion. It’s a simple combo that can be easily dressed up or down depending on your plans.
Outfit #11
Outfit is: White puff-sleeve oversized shirt + Black straight-leg pants + Red sandals + Red beaded necklace + Black shoulder bag
My note: No matter what styles are trending, classic pieces like the white puff-sleeve button-up shirt remain a go-to season after season. There’s no outfit formula as reliable as pairing it with black straight-leg pants, red sandals, a red beaded necklace, and a black shoulder bag. This combination is timeless and effortlessly pulled together.
Outfit #12
Outfit is: Cream oversized knit sweater + Green tie-dye wide-leg pants + Beige sandals + Black sunglasses
My note: Consider this your second & last reminder that button-up shirts can be styled for any occasion, even casual summer outings! Make this look stand out by pairing a mint green button-up shirt with light blue straight-leg jeans, green heeled sandals, and a matching mini handbag. Complete the outfit with black sunglasses for a fresh, cohesive summer ensemble.
