Craving looks that feel like a hug but still crush on the sidewalk? These baggy, relaxed outfits bring big energy with zero effort. We’re talking oversized silhouettes, clever layering, and accessories that scream “I woke up like this—on purpose.” Ready to go comfy and still look ridiculously cool?
1. Slouchy Blazer And Parachute Pants Power Move
This look nails the “I’m busy, but also iconic” vibe. A roomy blazer over billowy parachute pants keeps proportions dramatic and chic. You’ll look polished without losing that laid-back swagger.
Outfit Pieces:
- Oversized charcoal blazer
- Lightweight parachute pants in olive or grey
- Boxy cotton tee in white
- Chunky leather sneakers
- Minimal hoop earrings and structured crossbody
Styling Tips:
Keep the tee loose, but tuck the front for shape. Push blazer sleeves to the forearm for that effortless roll. Add socks that peek over sneakers for a streetwear touch.
Wear it to coffee meetups or casual workdays. Swap the tee for a striped knit when temps drop and add a baseball cap for cool-girl energy.
2. XXL Hoodie With Tailored Trousers, Because Balance
An oversized hoodie paired with dressy trousers feels rebellious in the best way. You get coziness up top and sharp lines below. It’s street style with grown-up credibility.
Outfit Pieces:
- Baggy hoodie in heather grey or cream
- Wide-leg pleated trousers in black
- Platform loafers
- Sporty watch and sleek belt
- Mini shoulder bag
Styling Tips:
Let the hoodie sit over the waistband, no tuck needed. Choose trousers with a crisp front crease for contrast. Add a subtle lip color to elevate it.
Perfect for gallery hopping or a casual date. Try a monochrome palette for an even more polished, minimalist effect.
3. Boxy Denim Jacket And Baggy Cargo Jeans
Double down on denim, but keep it relaxed. A boxy jacket and loose cargos create that skater-adjacent cool without trying too hard. It’s durable, practical, and ready for anything.
Outfit Pieces:
- Oversized denim jacket
- Baggy denim cargo jeans
- Fitted ribbed tank in white
- High-top canvas sneakers
- Baseball cap and stacked rings
Styling Tips:
Keep the tank fitted to anchor the volume. Cuff the jeans to show off your sneakers. Add a belt with a metal buckle to break up the denim-on-denim.
Wear it for weekend errands or a casual concert. Swap the tank for a striped long-sleeve when the weather cools.
4. Oversized Trench With Baggy Sweats That Look Chic, Not Lazy
This combo says “off-duty model” in three seconds flat. The coat elevates your sweats from couch to cafe real quick. Comfort and polish finally get along.
Outfit Pieces:
- Long oversized trench in camel or sand
- Baggy sweatpants with elastic cuffs
- Cropped hoodie or boxy sweatshirt
- Clean white trainers
- Rectangular sunglasses
Styling Tips:
Match the sweat set for a put-together look. Tie the trench belt behind you to define the shoulders. Keep the palette neutral for a luxe vibe.
Ideal for travel days or coffee runs. Throw on chunky gold hoops to dial up the sophistication, seriously.
5. Big Button-Down And Slouchy Dad Jeans
The baggy shirt and roomy jeans combo hits that quiet-cool sweet spot. It’s breezy, easy, and ultra-wearable. Consider it your “what do I wear?” solution.
Outfit Pieces:
- Oversized cotton button-down in blue or white
- Light-wash dad jeans with a relaxed leg
- Leather belt with minimal buckle
- Sleek ankle boots or retro sneakers
- Delicate layered necklaces
Styling Tips:
Half-tuck the shirt for a nonchalant finish. Roll sleeves to mid-forearm. Add a thin belt to give structure without losing the ease.
Perfect for brunch, casual meetings, or museum days. Swap the button-down for a silk one at night for instant upgrade.
6. Balloon-Leg Trousers With Boyfriend Leather Jacket
Voluminous trousers paired with a roomy leather jacket create a dramatic silhouette. It’s edgy yet comfortable, and it photographs like a dream. You’ll look like you own the street.
Outfit Pieces:
- Boyfriend-fit leather jacket
- Balloon-leg trousers in black or charcoal
- Fitted mock-neck top
- Chunky combat boots
- Chain necklace and boxy tote
Styling Tips:
Keep the top streamlined to balance the volume. Let trousers pool slightly over boots for that slouchy finish. Add a bold lip for a hint of glam.
Ideal for dinner and a show, or late-night walks. Swap the mock-neck for a graphic tee for daytime attitude.
7. Oversized Knit With Baggy Faux-Leather Pants
Texture play makes this look pop. A chunky knit paired with soft, wide faux leather feels plush yet tough. It’s equal parts cozy and cool.
Outfit Pieces:
- Chunky oversized sweater in cream or moss
- Baggy faux-leather pants with drawstring or elastic waist
- Minimal sneakers or hefty lug-sole boots
- Small huggie earrings
- Soft shoulder bag
Styling Tips:
Front-tuck the sweater slightly to show the waistband. Choose a sweater with roomy sleeves to emphasize the slouch. Keep accessories understated so the textures shine.
Great for lunch dates or office-casual days. Add a long coat and scarf when it’s chilly.
8. Mega Tee Dress With Oversized Bomber
Turn a giant tee into a dress and top it with a voluminous bomber. The vibe screams downtown-cool and gives legs the spotlight. It’s playful and unbelievably comfy.
Outfit Pieces:
- Extra-oversized graphic tee (long enough for dress length)
- Oversized bomber jacket
- Ribbed crew socks
- Chunky dad sneakers
- Crossbody phone pouch
Styling Tips:
Add bike shorts underneath for peace of mind. Scrunch socks just above the sneaker line. Pick a bomber with a glossy finish for contrast.
Perfect for street festivals or quick errands. Throw on a beanie if you want extra edge.
9. Baggy Tracksuit With Trench And Heels (Trust Me)
A slouchy tracksuit under a classic trench, then heels. The contrast feels unexpected and fresh. You get sporty comfort with a boss-lady twist.
Outfit Pieces:
- Oversized matching tracksuit (hoodie + joggers)
- Long trench coat in tan or olive
- Pointed-toe kitten heels
- Sleek sunglasses
- Structured mini bag
Styling Tips:
Keep colors cohesive: tonal tracksuit + neutral trench. Let the joggers skim the ankle to spotlight the heels. Minimal jewelry to keep it sharp.
Wear it to dinner after a long day or for city strolls. Swap heels for platform boots if sidewalks are unfriendly.
10. XXL Cardigan With Wide-Leg Jeans And A Cap
Grandpa sweater energy, but make it cool. The oversized cardigan adds warmth and personality, while wide-leg denim grounds the look. It’s a cozy classic with street cred.
Outfit Pieces:
- Oversized cardigan in heather or striped
- Wide-leg jeans in mid-wash
- Simple tank or baby tee
- Low-profile sneakers
- Baseball cap and tiny pendant necklace
Styling Tips:
Wear the cardigan open to maintain vertical lines. Choose jeans with a high rise to lengthen the legs. Add a cap to keep it relaxed and modern.
Great for library days, coffee shops, or casual Fridays. Belt the cardigan for a new silhouette when you want variety.
11. Baggy Shirt Dress With Over-The-Knee Socks And Creepers
A roomy shirt dress keeps things breezy while playful socks and chunky shoes add attitude. It’s schoolgirl-meets-street style done right. You’ll look fun, not fussy.
Outfit Pieces:
- Oversized shirt dress in striped or solid
- Over-the-knee ribbed socks in black or charcoal
- Platform creepers or chunky loafers
- Leather crossbody
- Minimal hoops
Styling Tips:
Add a thin waist belt if you want shape. Let the cuffs peek out and leave a few top buttons undone. Keep makeup fresh to balance the edge.
Perfect for coffee dates, bookstore hangs, or day parties. Swap socks for tights when the weather turns.
12. Slouchy Knit Set With Puffer And Beanie
Matching knits feel luxe and lazy in the best way. The puffer adds street attitude and structure. You’ll stay warm without sacrificing style.
Outfit Pieces:
- Oversized knit sweater and matching wide-leg knit pants
- Cropped puffer jacket
- Chunky sneakers
- Beanie
- Soft crossbody
Styling Tips:
Choose a monochrome set for a sleek column effect. Slightly crop the puffer to define the waist. Add delicate rings to keep it polished.
Great for weekend markets or winter walks. Switch the sneakers for shearling-lined boots on colder days.
13. Oversized Rugby Shirt With Baggy Chinos And Retro Runners
Preppy meets skater in this gloriously comfy outfit. The boxy rugby top and loose chinos look playful and easy. It’s nostalgic, but not costume-y.
Outfit Pieces:
- Oversized rugby shirt with bold stripes
- Baggy chinos in stone or khaki
- Retro running sneakers
- Canvas tote
- Sport watch
Styling Tips:
Layer a fitted long-sleeve under the rugby if it’s chilly. Let chinos puddle slightly for that relaxed finish. Keep accessories sporty and simple.
Perfect for campus vibes or casual weekends. Add a windbreaker for an extra layer and color-block moment.
14. Big Graphic Crewneck With Satin Midi And Skater Sneakers
High-low dressing at its finest. The oversized sweatshirt keeps it casual; the satin skirt brings shine and movement. It’s a vibe that says “I planned this” without the effort.
Outfit Pieces:
- Oversized graphic crewneck
- Bias-cut satin midi skirt in black or jewel tone
- Skater-style sneakers
- Compact shoulder bag
- Gold hoops
Styling Tips:
Front-tuck the crewneck slightly to show the skirt’s drape. Keep the skirt mid-calf so sneakers stay visible. Add a glossy lip for balance.
Great for casual dinners, art openings, or date night. Swap sneakers for ankle boots for a dressier finish.
15. Oversized Utility Vest With Baggy Joggers And A Longline Tee
Utility but make it chic. The roomy vest adds pockets and structure, while slouchy joggers keep it easy. It’s practical, cool, and very street.
Outfit Pieces:
- Oversized utility vest in olive or black
- Baggy joggers with cuffed hems
- Longline tee in white or grey
- Trail sneakers
- Bucket hat and sleek sunglasses
Styling Tips:
Let the tee extend past the vest hem for layers. Choose joggers with a slightly structured fabric so they don’t collapse. Keep colors tonal for a modern, utilitarian feel.
Wear it to street fairs, hikes-to-brunch, or any day you need pockets on pockets. Add a lightweight scarf for extra flair, FYI.
There you go—15 comfy, baggy, throw-on-and-go outfits that still look seriously put together. Mix pieces, play with volume, and trust your instincts. Your sidewalk runway awaits, IMO.
