Is there any outfit combo I love more than an oversized shirt and… well, pretty much anything? I don’t think so! It’s one of those magical pieces that’s so easy to throw on but always looks intentional.
I’ve been playing around with different looks, and I’ve found some winning combinations that I just had to share.
1. White Shirt with Black Separates
I am all about a monochrome moment, and this look is just so sleek. You start with a simple base of a black crop top with some black wide-leg pants.
Then, you just toss a crisp white button-up shirt over it for a really sharp contrast. I’d finish it off with some white sneakers to tie it all together.
What I love is how this outfit can go from casual to a bit more formal just by changing up your accessories.
2. Embroidered Shirt with Maxi Skirt
For those days you’re feeling a little bohemian, this outfit is such a dream. Grab an embroidered oversized shirt and style it with a flowy maxi skirt for that perfect free-spirited vibe.
The detailed embroidery gives the look so much visual interest, and the skirt adds a beautiful sense of movement.
To keep it grounded and ready for a day of walking around, I’d go with a pair of comfy sneakers.
3. Oversized Denim Shirt with Black Skinny Jeans
If you want an outfit with a little bit of edge, this one is a total winner. Pairing an oversized denim shirt with some sleek black skinny jeans creates such a cool contrast in the proportions.
I think adding some black ankle boots really elevates the whole thing and gives it a polished feel. This look is so versatile; you could wear it to a casual office or for a fun night out.
4. Light Blue Shirt with Jeans and Heels
Planning a special night? This outfit is your new go-to. A light blue oversized button-up shirt gives off such a soft, friendly vibe.
Style it with light wash wide-leg jeans to keep the look on-trend and casual. The real game-changer here is a pair of white strappy heels.
They add the perfect touch of glam and make your legs look amazing. It’s such a great balance of casual and dressy.
5. Shirt Dress with Lace Collar
Who says oversized can’t be romantic? I love this idea of choosing a shirt dress that has a pretty, delicate lace collar. It adds such a sweet, feminine touch.
Pairing it with matching knee-high boots creates a really cohesive and stylish outfit from head to toe. This is just perfect for a date night, giving you that ideal blend of comfort and pure elegance.
6. Light Blue Oversized Shirt with Black Maxi Skirt
You can truly never go wrong with pairing denim and black. For this look, a light blue denim oversized shirt goes so well with a sleek black maxi skirt.
The difference between the casual denim and the elegant skirt strikes a beautiful balance. It feels both laid-back and sophisticated at the same time. Just add black shoes to complete the outfit.
7. White Shirt with Black Trousers
Nothing has that timeless elegance quite like a white shirt paired with black trousers. Take a white oversized button-up and style it with some sleek black wide-leg trousers for a look that feels both chic and comfortable.
I’d add strappy sandals for a touch of warmth and, of course, black sunglasses for that extra cool factor. It’s a perfect outfit for the office or a business lunch.
8. Blue-White Striped Shirt with Wide-Leg Jeans
I am loving this nautical-inspired vibe. A blue and white striped button-up shirt with some light wash wide-leg jeans creates such a breezy, ready-for-summer feeling.
To finish the look, I’d slip on some white sneakers for a comfortable and stylish outfit that’s so great for a casual weekend brunch.
9. Oversized Pink Shirt with Gray Pants
This is such a cheerful way to add a pop of color to your wardrobe. An oversized pink button-up shirt paired with gray wide-leg pants makes for a look that’s fun but still feels balanced.
The pink shirt is so playful, while the gray pants keep things grounded. Complete the whole thing with pink chunky sneakers to really lean into that fun color.
10. Light Blue Button-Up Over White Tee
Layering is always the answer for adding some depth to your outfit. I’d start with a crisp white t-shirt as the base, then throw on a light blue button-up.
Just leave it open for a really relaxed feel. This combination looks great with dark wide-leg pants, which add a nice contrast.
Finish it all off with some comfy sneakers for an effortlessly cool look.
11. White Shirt with Olive Pants
Are you looking for an office-appropriate look that is still super stylish? Try styling a white oversized button-up shirt with some olive wide-leg pants.
The sharp white shirt feels professional, but the olive pants give your workwear a modern twist. I think adding pointed-toe shoes is the perfect way to give it a polished finish.
12. White Button-Up with Denim Shorts
When it starts to get warm out, this outfit is a definite must. Layer a white button-up shirt over a black crop top for a little extra dimension.
Pair that with some light blue denim shorts for a totally classic summer vibe. I’d just slip on some mule sandals for an easy, breezy style. This is my go-to for a picnic or a walk on the beach.
13. Bright Yellow Shirt Over Black Ensemble
If you are hoping to make a statement, this outfit is for you. Start with a black crop top and black wide-leg pants as your foundation.
Then, throw on a bright yellow oversized shirt for a pop of color that is absolutely going to get noticed. I’d finish it with white sneakers to keep all the attention on that bold shirt.
14. White Shirt with Wide-Leg Jeans and Mary Janes
I absolutely love this retro-inspired look. A white button-up shirt paired with light wash wide-leg jeans creates such a relaxed yet stylish feel.
Add a black belt to define your waist. But the real standout piece? A pair of black Mary Jane shoes. They add so much vintage charm to the whole outfit.
15. Striped Shirt with High-Waisted Jeans
Mixing up patterns and textures can result in such a visually interesting outfit. Start with a striped oversized shirt and layer it over a simple crop top.
I love pairing this with high-waisted jeans to create a really flattering shape. To give the outfit an edgy little twist, just add some boots. This is a great look for a casual day or even a concert.