Baggy denim is having a real moment, but its roots reach far beyond the latest wave of TikTok trends. Sliding into a pair of oversized jeans brings back flashes of 90s It-Girl style, marked by comfort, confidence, and a dash of attitude. Relaxed fits, soft textures, and a laid-back spirit turned simple denim into something magnetic—a favorite of anyone who didn’t feel the need to dress for anyone but themselves.
Aaliyah in wide-legged jeans and crop tops, Winona Ryder’s easy city looks, and Kate Moss strolling in loose denim—these images are still fresh for anyone who loves fashion’s sense of play. The style was easy to wear and endlessly versatile, mixing sporty basics with hints of glam, or bold accents with casual pieces, and always inviting a bit of personality. Now, baggy jeans are back in the spotlight, blending nostalgia with a feeling of new possibility.
Whenever I find myself searching for fresh inspiration, I come back to the playful energy of 90s It-Girls and their love for baggy denim. These outfits always remind me how a simple pair of jeans can shift your whole mood—sometimes relaxed, sometimes bold, and often just the nudge I need to try something new with my own style.
I’m sharing 14 baggy denim ensembles that bring back the unmistakable cool of 90s It-Girls.
The Classic White Tee and Baggy Jean Combo
Some days start with the simplest instincts—rolling out of bed, grabbing a soft white tee, and wearing your most reliable jeans. There’s a reason this pairing refuses to go out of style. The structure of a crisp, oversized tee tucked into roomy denim feels endlessly fresh, echoing the looks worn by off-duty models and street style stars.
You can add subtle touches to make the outfit your own. A messy tuck, a chunky sneaker, and a vintage belt give the look personality without ever feeling try-hard. Gold hoops or a watch with a thick leather strap elevate things just enough. On late mornings, I find myself reaching for this combination again and again, reminded that sometimes, confidence starts with comfort.
If you want to add a layer, try a boxy denim jacket or a flannel shirt slung over your shoulders. That bit of extra fabric, that soft weight, can shift the mood of the outfit and make it feel even more relaxed.
Cropped Tops with High-Waisted Baggy Jeans
There’s a certain energy that comes from balancing proportions—where a fitted crop top meets the loose sweep of high-waisted denim. This silhouette feels both nostalgic and current, nodding to the 90s while leaving plenty of room for your own twist.
On humid days, a ribbed tank or shrunken tee works well. For evenings, a silky cropped blouse or long-sleeve mesh top brings a little attitude. When I first tried this combo, I felt exposed, but the volume of the jeans gave me a sense of ease I didn’t expect. Sneakers or heeled boots both work, depending on your plans.
Accessories tell the rest of the story. I like a tiny shoulder bag and oversized sunglasses, the kind that make even the most casual outfit feel a little more put-together.
Denim-on-Denim: Double the Texture, Double the Fun
Pulling off denim-on-denim always feels a little daring, but it’s rooted in the 90s, where icons mixed washes, shapes, and fits without a hint of hesitation. A baggy jean paired with a slouchy denim jacket creates instant texture and presence. The trick lies in choosing slightly different shades, so the look feels layered instead of flat.
Layer a white tank or a graphic tee underneath, and let your shoes do the talking. Platform sneakers or strappy sandals add playful contrast. For accessories, a bold hair clip or even a bucket hat can finish the outfit on a high note.
Wearing this out with friends, I’ve caught myself feeling a new sense of confidence. Something about the doubled-up denim makes me walk a little taller, almost like channeling that laid-back coolness the 90s It-Girls wore so naturally.
Oversized Blazers and Baggy Jeans
Power dressing took on a new form in the 90s. Oversized blazers layered over baggy jeans bring a casual, unbothered vibe that still manages to feel sharp. A tailored blazer, especially in a neutral or pastel, instantly polishes denim, while a graphic tee or tank underneath keeps things playful.
I once wore this mix to an early-morning meeting, sneakers squeaking on the tile, coffee in hand. The blazer pulled the look together, and the jeans softened the formality, making the whole thing feel intentional rather than stuffy. Add chunky jewelry or a structured bag for a finish that feels grown-up but still approachable.
On chillier days, swap the tee for a lightweight turtleneck, and let the sleeves peek out from under the blazer for a layered look with depth and texture.
Sporty Spice: Hoodies and Baggy Denim
Some mornings, comfort is non-negotiable. A soft hoodie paired with baggy jeans offers an outfit that’s equal parts nostalgic and practical. This combo channels the sportier side of 90s style, bringing to mind girl bands and weekend skate parks.
The fit of the hoodie can change the vibe. A cropped style keeps things neat, while a super oversized pullover leans into that lived-in feel. I love this outfit for running errands, grabbing groceries, or even just curling up with a book in a sunny window. A baseball cap and dad sneakers finish the look, proving that low-key can still have plenty of personality.
Slip Tanks and Distressed Baggy Denim
Delicate, slinky tanks paired with heavily distressed baggy jeans create a sense of tension that feels both intentional and a little rebellious. The contrast between silk and frayed denim brings texture and depth, offering an echo of the grunge-meets-glam mood that defined 90s pop culture.
Layer necklaces or add a bold lip color for an evening out. A simple sandal or strappy heel keeps things from looking too undone. I once wore this to a backyard party, catching the breeze through rips in the denim, the cool silk clinging to my skin. It felt spontaneous and entirely right for the night.
Oversized Sweaters Tucked into Baggy Jeans
Cool weather calls for soft, slouchy knits, especially when paired with relaxed denim. Oversized sweaters loosely tucked at the front of baggy jeans create an effortlessly casual silhouette, perfect for weekend brunches or afternoons spent wandering through city streets.
The key is to keep the sweater relaxed without overwhelming your frame. A French tuck at the front, sleeves pushed up, and simple jewelry like stacked rings or a chunky bangle add shape and interest. I’m partial to sweaters in muted shades—think oatmeal, faded blue, or soft blush—which play nicely against faded denim.
Boots or classic trainers complete the look, and if you feel like adding a little something extra, a crossbody bag with metallic details can pull everything together.
The Grunge Remix: Plaid Shirts and Baggy Denim
Grunge never really disappeared—it simply evolved. A plaid flannel shirt layered over a ribbed tank and baggy jeans brings a dose of 90s attitude that still feels relevant. Tie the shirt at the waist, or wear it loose with a few buttons undone for a more relaxed take.
I wore this outfit to a late-night concert once, hair in a messy bun and lips stained dark red. The music thumped, and every time I caught my reflection, I felt a bit like the rebellious It-Girls I admired growing up. Dr. Martens or classic Converse ground the look and bring an authentic edge.
Add a canvas tote or a tiny backpack, and you’re set for anything the day throws at you.
Statement Belts and Baggy Jeans
Sometimes, the smallest detail transforms everything. A wide, studded belt looped through loose denim instantly changes the mood of your outfit, nodding to the 90s when accessories spoke volumes. Pair with a fitted tank or graphic tee, and let the belt be the centerpiece.
This is an easy way to experiment without overthinking. I’ve found that playing with different belt styles—vintage leather, metallic, or even chain belts—adds new life to the same pair of jeans. Minimal sneakers or chunky boots work well here, and if you want to lean into the 90s vibe, add a pair of oval sunglasses or a velvet scrunchie.
Baggy Jeans and Platform Sandals
Platforms have a special place in my memory, thanks to the Spice Girls and those sky-high shoes that seemed to defy gravity. Wearing baggy jeans with platform sandals brings a bit of that playful spirit into everyday outfits.
Try cuffing the jeans so the shoes peek out, adding length to your legs and a bounce to your step. Pair with a bright tank or a ruffled blouse for a softer take, or keep things minimal with a black bodysuit. I wore this mix on vacation last year, and it turned every stroll into a small celebration.
Toss on a straw hat or big earrings if you’re feeling adventurous. There’s joy in leaning into the drama sometimes.
Band Tees and Ripped Baggy Denim
Worn band tees—soft with age, faded just right—never go out of style. Pairing them with ripped baggy jeans channels that backstage energy of 90s concerts and music videos.
I like to knot the tee at the waist or roll up the sleeves for shape. Add stacked necklaces, slip into worn-in sneakers or combat boots, and head out for the day. The best thing about this look is its authenticity. Every tee tells a story, every rip in the denim carries a little history.
Throw on a corduroy jacket if the weather turns cool, or keep it light with a flannel shirt tied at your hips.
Pastel Denim and Baggy Silhouettes
Who says denim has to be blue? Pastel shades—mint, lilac, blush—bring a dreamy twist to baggy jeans, softening the edges and brightening your mood. Pair with a fitted white top, delicate jewelry, and simple sandals for a fresh look.
I once wore pale pink jeans to a summer picnic, toes in the grass, basket in hand. The color felt playful and surprisingly versatile, especially with light layers and dainty accessories. A straw bag or translucent sunglasses add a finishing touch.
Cropped Jackets and Wide-Leg Baggy Jeans
Proportion play takes center stage with a cropped jacket layered over wide-leg baggy jeans. The short length of the jacket highlights your waist, while the jeans add volume and movement.
Try a denim jacket, bomber, or even a boxy corduroy style. A fitted tank or bodysuit underneath keeps the outfit balanced. I’ve reached for this look on chilly spring mornings, feeling both put-together and free to move.
Low-top sneakers or loafers add polish, and a structured handbag brings everything together.
Baggy Overalls: The Ultimate 90s Throwback
Overalls, especially in faded denim, are pure nostalgia. Wear them loose over a striped tee or cropped tank, and let one strap hang down for a playful touch. There’s an ease to overalls that feels almost childlike, a reminder that fashion can be as fun as it is expressive.
Lace up some canvas sneakers, tie a bandana in your hair, and you’re ready for anything from errands to late-night ice cream runs. I’ve found that overalls invite conversation and compliments wherever you go, carrying a little 90s spirit into every room.
Vintage-Inspired Layers with Baggy Denim
Mixing textures and layers takes baggy denim to a whole new level. Pair with a vintage sweater vest, a floral blouse, or a leather jacket for dimension. The beauty of this approach is that nothing has to match perfectly. The joy comes from mixing prints, textures, and memories.
One rainy afternoon, I paired baggy jeans with a borrowed cardigan and my favorite platform boots. The outfit felt like a patchwork of past and present, practical yet packed with personality.
Layer on accessories—think beaded necklaces, silk scarves, or enamel pins—and let your outfit tell its own story.
