So maybe you’re wondering the best ways to wear plaid because you’re seeing it everywhere and you’re a little tempted but it is kind of preppy and you’re just not sure since the last time it was hot you were in college and..hey! Get out of my head!
Yes, yes, plaid is everywhere these days. But it can be a little tricky to pull off without a professional stylist (or a yacht club membership), so I did a little searching to find some of the coolest plaid pieces that I think will make awesome additions to any fall and winter wardrobe. What I really like is while the pattern is totally on trend now, it’s definitely wearable beyond this season. Just ask your friends who never stopped wearing it in the first place.
Late night lecture bag ($64.99 at ModCloth)
I’ve found so many fun, affordable bags at Modcloth, so it’s no surprise that I discovered this late night lecture bag there that I can’t stop thinking about. I’m digging the brown leather handles against the black and white plaid, plus the leather bottom adds a fabulous touch.
BB Dakota plaid cardigan ($105 at Shop Bop)
I don’t know about you, but I live in sweater jackets all winter long. I love the simplicity of this plaid cardigan from BB Dakota that’s flattering on all shapes and sizes. Black and white is still hot right now too, with no signs of going away, so this lets you hit two trends with one relatively affordable outerwear purchase. Awesome.
Vince Camuto urban plaid scarf ($36 at Nordstrom)
This urban plaid scarf by Vince Camuto is a fab change from the typical plaid pattern and color palette, if you’re not really a traditionalist. Such a cool way to infuse the trend into your wardrobe without the bold navys, greens, and reds.
Debutante plaid wristlet ($128 at Henri Bendel)
I can see myself carrying this Bendel’s plaid wristlet all the time, from a date night to a lunch with friends. The bold exposed zipper adds just the right amount of edge for me, but the classic shape makes it such a versatile piece I know it will be a go-to for many years.
Gap plaid wool trouser shorts ($49.95 at Gap)
So a plaid skirt is probably the most ubiquitous piece of clothing, but for me it’s a little too preppy. That’s why I’m loving the twist in these plaid wool trouser shorts from the Gap. While I’m a huge fan of wearing dressy shorts to parties and date nights, I know they’re not for everyone. (So don’t yell at me!) But if you’re willing to give it a try–with some black opaque tights and cool black booties, perhaps?–I think you’ll be quite pleased with the result.
Sam Edelman plaid ballet flats ($110 at Shop Bop)
I’ve always had great luck with Sam Edelman shoes. They wear really well and they’re super comfortable, which is why I’m thinking I might need to add these plaid ballet flats to my collection. You could wear them with dark skinny jeans and a white or denim oxford shirt, or pair with a skirt for work. Just not a plaid skirt.
alice + olivia Selma drop waist dress ($358 at Shop Bop)
There’s probably nothing preppier than a plaid dress, but leave it to alice + olivia to design an update that’s super stylish. The cap sleeves lie fairly flat, for those of us who aren’t loving our upper arms (raising hand here) and the flip skirt will be flattering over the post-baby hips. You just need great legs for sure–though opaque tights will help. The subtle pattern means it’s definitely a dress I’d keep wearing, even when plaid is back to just a hipster staple.
Autumn Cashmere plaid crewneck sweater ($396 at Piperlime)
In my experience, plaid pullover sweaters tend to skew a little more mature than I’d like, but this Autumn Cashmere plaid crewneck sweater is so young and hip with a more cropped cut and modern pattern. I love it styled over the leather pants, or maybe these faux-leather leggings (my favorites!), if you dare. But hey, jeans work too, or even a great pencil skirt.
Rails Hunter plaid shirt ($138 at Intermix)
I was so excited to finally find the perfect feminine-cut, tapered plaid shirt, which is exactly how I see the Rails Hunter plaid shirt. Apparently, I’m not alone because after I pinned it on my style inspiration Pinterest board, the red one sold out. Thankfully, they’ve got a couple of other color palettes available. But hurry, they’re selling fast.
Sam Edelman plaid slip-on sneaker ($69.99 at Urban Outfitters)
Yeah I know, more Sam Edelman. But with the slip-on sneaker so popular (and comfy) right now, I couldn’t resist these plaid slip-on sneakers. They’re a great alternative to sporty running shoes or clogs or whatever your go-to mom shoe might be. (Admit it, we all have one.) And the leather trim? So stylish!
For more cool style picks for women, check our archives, or follow our Just Our Style Pinterest Board. Cool Mom Picks is a reward style affiliate.
