If there's one bottoms trend that will never get old, it's baggy jeans. I've had the same pair of baggy jeans for years, and I always bring them out for the warm seasons. Baggy jeans just have the essence of cool, chic, and fun, which are the exact words I want used when someone describes the way I dress for spring and summer. How am I doing that with a pair of baggy jeans? I'm dressing them up in new, chic ways with the best shirt trends to wear with baggy jeans. When I get dressed, my bottoms tend to be the focal point of an outfit, but now I'm switching things up.
I've been on the hunt for the best shirt trends to wear with baggy jeans, and lucky for me, I've struck fashion gold. Chic dressers on Instagram have paved the way to my new and improved outfits. These looks feature classic tops like polo shirts to innovative and fun trends like shirred tops. Whatever your aesthetic goals may be for the warm weather, keep scrolling for outfit inspiration, discover the best shirt trends to style with baggy jeans, and shop each look.
Polo Shirts
Polo shirts gained popularity again last year, thanks to Miu Miu's previous preppy-forward runway collection. Now, it seems fashion people are not nearly done with styling this preppy shirt trend, and I'm glad about it. I've been sporting polo tops since the weather got warmer, and I want mine to look less dated. What better way to make them look modern and fun than with a pair of baggy jeans? I find that polo shirts and baggy jeans are reminiscent of 90s outfit trends. In 2026, this outfit trend is getting a major refresh. Style your polo shirt with a pair of boots and baggy jeans for an everyday look. For a night outfit, trade those boots for pointed-toe, slingback heels, and put a leather mini bag over your shoulder to complete your look.
Shop Polo Shirts
Baby Tees
Baby tees will never get old in my book. This trend looks best with baggy jeans, to me. This outfit is the ultimate, laid-back, cool girl outfit. It's effortless, chic, and only a little intentional, very model-off-duty. I always want t o give off that vibe, in particular. This outfit below shows just how cool you can look in such simple pieces. Since the base of your outfit is pretty simple, accessorize with a satin scarf or bandana, a pair of pointed-toe shoes, and a shoulder bag, like this outfit below. It gives a very chic 90s vibe. If you want to dress it up more, just add a leather moto or cinch-waist jacket.
Shop Baby Tees
Prairie Blouses
I'm not much of a boho chic dresser, but prairie tops are changing my mind. I don't think I'll ever go full coquette with my aesthetic, but this shirt trend is opening my mind to new fashion possibilities. They are especially stylish with a pair of baggy jeans. I love the contrast between such a delicate top and bottoms that are so casual. For a daytime outfit, I recommend styling your prairie top like the look below, with baggy jeans, pointed-toe shoes, and a large leather tote bag. For a night out, trade that big bag for a small shoulder bag and add a light funnel-neck jacket, if the weather permits.
Shop Prairie Tops
Striped Lightweight Sweaters
I love a lightweight sweater during the spring, and it seems other fashion people would agree. When I'm stuck on how to style a pair of baggy jeans, I almost always reach for a lightweight sweater. This season is about lightweight striped sweaters, particularly. They add a fun element to an outfit, especially with different color combinations. Striped sweaters can be easily styled with baggy jeans, as seen below. If you're someone who likes to keep their looks casual, like me, just throw on a pair of pointed-toe, suede boots. If you're trying to dress up on a chillier day, layer a leather jacket over your lightweight sweater and a button-down underneath to look chic and intentional.
Shop Lightweight Striped Sweaters
Shirred Shirts
The shirred shirt trend had a major moment last summer, and I'm happy to say that it's so back. It's the perfect top to contrast a pair of casual, baggy jeans. Shirred tops always dress up an outfit, IMHO. Even if it's just a T-shirt or simple sleeveless top, the added texture gives an outfit the extra zhuzh you might need for a night out. It's also an easy top to style with any pair of bottoms, but it looks especially chic with a pair of baggy jeans. The look below is proof. If you really want to look cool, juxtapose your outfit even more with a pair of sneakers, similar to this look. If you want to dress up instead, just switch your sneakers for a pair of ballet flats or pointed-toe pumps.
Shop Shirred Shirts
Flowy Button-Down Shirts
I'm a casual dresser most of the time, so a flowy button-down is my go-to when styling a baggy pair of jeans. This spring and summer, I'm prioritizing comfort overall. The warmer seasons in NYC can be overwhelming to get dressed for; the lighter the layers, the better. Flowy button-downs give off an effortless vibe that chic dressers always have, and that's exactly what I'm going for the rest of the season. Try styling your baggy jeans with a pair of boat shoes or suede moccasins, and layer a flowy button-down over a tank top or tee, and complete your look with a woven bag.
If you want to look a bit more dressy, keep the same clothing items on, and trade your shoes for a pair of heeled strappy sandals, and your woven bag for a sleek black East West bag.
Shop Flowy Button-Downs
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