I have a bit of an obsession with jackets and coats, and the grandpa-chic trend is not making it any better. Every tab I open or social media app I browse has me wanting to add another oversized blazer or cardigan to my cart.
Each grandpa-inspired style is so different and gives off a unique vibe. That’s why we’ve rounded up the absolute best outfits to spice up your collection this season. Check them out below.
1. Sweater Vest and Pleated Skirt
Sweater vests are pretty much a must-have if you’re going for that scholarly grandpa core vibe. I love this preppy gray pinstriped mini skirt paired with a cozy vest and some classic black loafers.
For an extra touch of that vintage schoolgirl look, I’d totally add some knee-high socks. You could also layer a crisp button-up shirt underneath the vest for another cute option!
2. Ribbed Sweater, Denim Shorts, and Sneakers
Ribbed knits are having such a major moment right now, and this is a great way to give them a grandpa-inspired spin. For a more contemporary take on the trend, try styling a black ribbed sweater and charcoal cardigan with some blue denim shorts.
Finish the look with a pair of chunky white sneakers. I just love the juxtaposition between the fitted sweater and the loose shorts—it’s simple but definitely eye-catching.
3. Patterned Sweater and Baggy Jeans
Next up is a classic grandpa core uniform. This aesthetic is all about playing with proportions, so I’d reach for a loud patterned sweater and tuck it into some light-wash baggy jeans.
An oversized sweater and relaxed-fit denim are key here. To complete the look, you could go with white sneakers or some brown leather loafers. I also think belting the sweater over the jeans would be super cute.
4. Graphic Crop Top and Wide-Leg Pants
While so many grandpa core looks are built around oversized pieces, you can totally play with cropped tops too. This graphic white crop top is perfect for balancing out the volume of these teal wide-leg pants.
An orange chunky knit cardigan ties the whole outfit together, especially when you add in some coordinating platform sandals. This is such a fun and youthful ensemble!
5. Striped Sweater, Pleated Skirt, and Beanie
Last but not least, we have another darling preppy outfit. This one is made up of a striped sweater, a pleated mini skirt, and a ribbed beanie. I adore the varsity vibes you get from layering striped pieces.
For shoes, you could try patent leather Mary Janes or even some metallic Oxfords. This look is just so spunky and fun for school, work, or a weekend outing!
6. Leather Vest and Wide-Leg Jeans
You can channel your inner English professor with this combination. It features a dark button-up shirt, a brown leather vest, and some light wash wide-leg jeans. Loafers or Oxfords would suit this look so nicely.
I also love the idea of adding a leather elbow-patch cardigan or blazer over the vest to really lean into that scholarly feel.
7. Mustard Cardigan and Plaid Pants
Kicking things off, we have this gorgeous mustard cardigan paired with beige plaid wide-leg pants. I’m loving the texture contrast happening between the corduroy cardigan and the wool trousers.
A pair of brown suede loafers completes this perfect autumnal ensemble. You might really love trying out tonal outfit combinations like this one; neutral colors really help each piece stand out on its own.
8. Striped Polo Shirt and Wide-Leg Shorts
Polo shirts are such a great way to get that grandpa-inspired style, especially a classic striped one. Tuck it into some wide-leg shorts, add a belt, and finish the look with chunky black loafers for a relaxed weekend fit.
I’d probably wear some tall socks with this outfit to lean into that quirky grandpa vibe even more. You could also easily swap the shorts for some baggy jeans.
9. Plaid Overcoat and Corduroy Pants
Here’s a fantastic autumn and winter outfit idea. It starts with a plaid oversized coat styled with brown corduroy wide-leg pants and some classic black loafers.
I love how the different textures and colors complement each other so well. You might also enjoy layering a turtleneck sweater underneath the statement coat for extra warmth.
10. Knit Vest, Oversized Tee, and Cropped Pants
This is another great way to wear a knit vest. Just pair it with an oversized white tee and some cropped black wide-leg pants.
The relaxed proportions of this outfit, combined with the beige knit vest, totally nail that quirky grandpa style. I think some white or metallic Oxfords would be so cute with this look.
11. Colorful Sweater, Striped Pants, and Long Coat
One of my favorite looks is pairing a vibrant striped sweater with coordinating striped pants. When you add an extra-long cream coat, it elevates the whole outfit and gives it a smart, vintage vibe.
I’d wear white or brown loafers with this ensemble and maybe top it off with a fun printed scarf or a beanie. The color pairing possibilities are truly endless!
12. Textured Cardigan, Knit Skirt, and Black Top
Cozy textures are absolutely key for channeling that grandpa core aesthetic. This textured gray cardigan is the perfect complement to the fuzzy knit skirt.
To keep the look feeling modern, style it with a black sleeveless top and some fun jewelry or hair accessories. A pair of chunky loafers would complete this outfit so nicely.
13. Oversized Button-Up and Denim Culottes
For a relaxed weekend fit, you can’t go wrong with an oversized cream button-up shirt. It pairs perfectly with some light wash denim culottes.
Adding a cropped tank and black loafers keeps this outfit feeling young and fresh. This is such a comfy and casual way to do the grandpa core look.
14. Cargo Jeans and Platform Boots
Cargo pants are so on-trend right now, so why not give them a grandpa core twist? These dark wash cargo jeans look awesome with a navy sweater and some epic white platform boots.
Don’t forget to add fun accessories, like this navy plaid newsboy cap, to complete the quirky outfit. Grandpa core is all about embracing that carefree spirit!
15. Collared Shirt, Wide-Leg Trousers, and Long Coat
A collared button-up shirt paired with wide-leg trousers just oozes that vintage scholar appeal. Adding a long cream coat enhances the sophisticated effect even more.
The burgundy trousers really make a statement here. I’d pair them with some classic white leather loafers. This is an outfit that can take you from campus to cocktails seamlessly.
16. Multicolored Patchwork Sweater Dress
For a fabulous fall or winter outfit, you can’t go wrong with an oversized sweater dress. I mean, look at this multicolored patchwork one! Adding some black knee-high boots helps to pull the voluminous shape together.
I’d probably wear a collared shirt underneath for extra warmth and style, then finish it off with a fun printed scarf.
17. Checkered Skirt and Cropped Tee
Pleated skirts are another staple piece for the ultimate grandpa core outfit. This black and white checkered maxi skirt is paired simply with a dark cropped tee.
For shoes, go for black or brown loafers, Mary Janes, or Oxfords to dress up this casual look. A colorful cardigan would also add a fun twist.
18. V-neck Sweater and Light Wash Jeans
For another casual, grandpa-inspired outfit, try a navy v-neck sweater with some light wash baggy jeans. I love the preppy twist of layering a bright sweater over the shoulders.
This outfit combo is perfect for any laid-back weekend plans. Just throw on some colorful sneakers to complete the look.
I hope these 18 grandpa core outfit ideas have sparked some inspiration for trying out this comfy, vintage-inspired aesthetic! Let me know in the comments which outfit combo was your favorite.