17 Hipster Dress to Impress Outfit Ideas That Even Your Grandma Would Approve Of!

Hey there, trendsetters! So, you’ve been scrolling through your Insta feed, admiring those effortlessly cool outfits that make you wonder if you’re living your best life—or just stuck in a style rut.

We get it! You want to look chic and hipster without feeling like you raided a thrift store and came out wearing an entire collection of plaid.

Well, fear not! We’ve compiled a list of 17 hipster dress to impress outfit ideas that are not only stylish but also grandma-approved! Yes, you heard that right!

Ready to elevate your wardrobe while keeping it cozy enough for family gatherings? Let’s dive in!

1. Vintage-Inspired Blazer and High-Waisted Trousers

Opt for a vintage tweed or plaid blazer with bold patterns and pair it with high-waisted trousers. Add a quirky printed shirt underneath—think floral, polka dots, or abstract designs. Finish the look with retro-inspired brogues or chunky loafers. Perfect for a hipster take on business casual.

2. Oversized Denim Jacket with Graphic Tee

Wear an oversized, distressed denim jacket over a band graphic tee or one with an artsy, ironic print. Pair it with skinny jeans or cropped wide-leg pants for a laid-back, effortlessly cool vibe. Throw on a pair of vintage sneakers or boots, and don’t forget a beanie or fedora for extra hipster points.

3. Patterned Jumpsuit with Layered Accessories

Go for a statement patterned jumpsuit in bold, earthy tones or playful prints. Layer on some quirky accessories like a vintage scarf, layered necklaces, or retro sunglasses. Top it off with a wide-brimmed hat and heeled boots for a put-together yet laid-back look.

A photo of a woman with a hipster look wearing a patterned jumpsuit in earthy tones. She is accessorized with a vintage scarf, layered necklaces, and retro sunglasses. The outfit is completed with heeled boots and a wide-brimmed hat, giving a bohemian-chic, put-together style.

4. Flannel Shirt with Suspenders and Rolled Jeans

Channel a lumberjack chic vibe with a cozy, fitted flannel shirt tucked into rolled-up slim jeans. Add suspenders for a quirky, hipster twist. Pair with rugged boots and finish with a vintage leather belt. This look mixes practicality with a dash of throwback style.

5. Leather Jacket with Skinny Jeans and Chelsea Boots

A timeless hipster combo, go for a fitted leather jacket in black or brown, paired with skinny jeans. Underneath, wear a striped or vintage graphic tee. Chelsea boots or Doc Martens are a perfect shoe choice to keep things edgy. Add sunglasses and a minimalist tote bag for a polished, cool finish.

A photo of an edgy hipster outfit. There is a fitted leather jacket in black or brown, paired with skinny jeans. A striped or vintage graphic tee peeks out from underneath. The outfit is completed with sleek Chelsea boots or Doc Martens. Accessories like sunglasses and a minimalist tote bag are added to the polished, rebellious vibe.

6. Bohemian Maxi Dress with Ankle Boots

For a feminine hipster vibe, choose a flowing bohemian-style maxi dress with earthy tones or vintage floral prints. Pair it with ankle boots and add a denim or leather jacket for some structure. Layer on chunky jewelry like statement necklaces or oversized rings, and complete the look with a wide-brimmed hat.

A photo of a woman with a flowing bohemian-style maxi dress with earthy tones or vintage floral prints for a feminine hipster vibe. She is wearing ankle boots and a denim jacket. She has chunky jewelry, including a statement necklace and oversized rings. She is wearing a wide-brimmed hat. The background is a rustic setting with wooden beams and plants.

7. Corduroy Jacket with Turtleneck and Culottes

Wear a retro corduroy jacket in a rich autumnal shade like mustard, rust, or forest green. Pair it with a fitted turtleneck and high-waisted culottes or wide-leg pants. Accessorize with chunky boots, round glasses, and a crossbody satchel bag for a polished, intellectual look.

A photo of a woman with a retro corduroy jacket in a rich autumnal shade of mustard, rust, or forest green, styled in a hipster fashion. She is wearing a fitted turtleneck and high-waisted culottes or wide-leg pants. She is accessorized with chunky boots, round glasses, and a crossbody satchel bag. The background is blurred and contains a brick wall and greenery.

8. Tailored Suit with a Twist

Instead of the traditional suit, go for a more playful approach with mismatched patterns or colors. For example, pair a striped blazer with checked trousers, or choose a suit in an unconventional color like mustard, olive, or burgundy. Wear it with a fitted turtleneck or vintage band tee underneath for a modern hipster spin on the classic suit. Finish with loafers or lace-up boots.

A photo of a woman wearing a striped blazer with checked trousers. She is wearing a fitted turtleneck underneath the blazer. The woman is wearing loafers. The background is a street with buildings.

9. Oversized Sweater with Midi Skirt and Combat Boots

Wear an oversized sweater in a warm, neutral shade like oatmeal or rust, and pair it with a flowy, pleated midi skirt in a complementary color or fun pattern. Add some contrast with chunky combat boots or Dr. Martens for that perfect balance of softness and edge. Finish the look with a statement scarf or a beanie for those cooler fall days.

A photo of a woman wearing an oversized oatmeal sweater with a flowing, pleated rust midi skirt. She is wearing chunky combat boots. The woman is standing on a wooden platform. There is a statement scarf around her neck. The background is blurred and contains trees. The overall image has a warm, autumnal tone.

10. Retro Band Tee with High-Waisted Corduroy Pants

Channel a vintage vibe by pairing a retro band tee—think The Rolling Stones, Fleetwood Mac, or a thrifted find—with high-waisted corduroy pants. Opt for warm, earthy tones like mustard, rust, or olive. Add in a pair of classic Converse or vintage sneakers and layer with a cozy cardigan for an effortlessly cool, music-inspired outfit.

A photo of a woman wearing a retro band tee with a vintage hipster vibe. She has on high-waisted corduroy pants in a mustard color. The band tee is from The Rolling Stones. She is wearing classic Converse sneakers and a cozy cardigan. The background is a brick wall with graffiti.

11. Denim Overalls with a Striped Breton Shirt

Go for a pair of classic blue or black denim overalls and wear them over a striped Breton shirt for that timeless, Parisian-hipster vibe. Roll up the pant legs and pair with clogs or casual sneakers. A slouchy beanie and round sunglasses add to the laid-back, artsy feel of this look.

12. Statement Blouse with Cropped Wide-Leg Pants

Wear a statement blouse with dramatic sleeves or an eye-catching print—think polka dots, paisley, or floral. Tuck it into a pair of cropped, wide-leg pants for a sophisticated, yet quirky outfit. Finish the look with chunky platform shoes and a structured bag, giving off an artsy, gallery-opening vibe.

A photo of a woman wearing a statement blouse with dramatic sleeves and a bold eye-catching print. She is wearing the blouse tucked into a pair of cropped, wide-leg pants. The woman is also wearing chunky platform shoes and carrying a structured bag. The background is a gallery with modern art.

13. Graphic Sweater with Patterned Midi Skirt

Opt for a graphic sweater with quirky or ironic prints and tuck it into a patterned midi skirt, like plaid or polka dots. The mix of prints creates a playful and unique look. Add platform loafers or classic ankle boots, and layer with a long trench coat for an urban, city-chic style.

A photo of a woman wearing a graphic sweater with quirky prints and tucking it into a patterned midi skirt. The mix of prints creates a playful and unique look. She is wearing platform loafers and a long trench coat. The background is an urban setting with brick walls and graffiti.

14. Utility Jacket with Vintage Dress

Layer a rugged, military-inspired utility jacket over a vintage floral or paisley dress. The mix of feminine and tough creates a cool contrast. Wear with ankle boots or chunky sneakers, and add some pins or patches to the jacket for a personalized, DIY flair. It’s perfect for fall weather and music festivals.

A photo of a woman wearing a military-style utility jacket over a vintage floral dress. The dress has a paisley pattern and is in vibrant colors. The woman has brown hair and is wearing white sneakers. The background is a city street with tall buildings. The lighting is soft.

15. Turtleneck Under Slip Dress

Take a sleek, satin slip dress and layer a fitted turtleneck underneath in a contrasting color. Pair with chunky boots or platform sneakers for a casual twist. Add in some bold earrings and a slouchy tote bag for a look that’s both 90s-inspired and modern.

A photo of a woman wearing a sleek, satin slip dress layered with a fitted turtleneck underneath in a contrasting color. She is wearing chunky boots and has bold earrings. She also has a slouchy tote bag. The background is blurred and contains a building with a patterned facade.

16. Plaid Suit with Sneakers

Wear a tailored plaid suit in a classic color like gray or tan, but instead of dress shoes, pair it with clean, white sneakers. Layer with a t-shirt or turtleneck for a relaxed feel, and add a newsboy cap for an extra touch of hipster flair. It’s perfect for a day in the city or a casual night out.

A photo of a woman wearing a tailored plaid suit in a classic color like gray or tan. Instead of dress shoes, she pairs it with clean, white sneakers. She layers with a t-shirt or turtleneck for a relaxed feel. She adds a newsboy cap for an extra touch of hipster flair. The outfit is perfect for a day in the city or a casual night out.

17. Velvet Blazer with Vintage Denim

Combine a luxurious velvet blazer in a jewel tone like emerald or deep burgundy with a pair of vintage, high-waisted denim. Underneath, wear a simple tee or lace camisole for texture contrast. Pair with ankle boots and a wide-brimmed hat for a look that’s effortlessly glamorous and laid-back.

A photo of a woman wearing a luxurious velvet blazer in a jewel tone like emerald or deep burgundy with a pair of vintage, high-waisted denim for a hipster vibe. Underneath, she wears a simple tee or lace camisole for texture contrast. She pairs this outfit with ankle boots and a wide-brimmed hat, creating a look that is effortlessly glamorous and laid-back.

Wrap-Up

There you have it — 17 hipster dress to impress outfit ideas that will make you the star of every family gathering while keeping your cool factor on point! Whether you’re sipping lattes at your favorite café or hitting up an art show, these looks are versatile enough to handle anything life throws your way.

So, why not channel your inner hipster with confidence? With these outfits, you’ll not only turn heads but also win your grandma’s heart. Now go forth and slay, because looking good should never feel like a chore! Happy styling!