I just got back from a few weeks bopping around Portugal, and the local style was exactly what I’ve been craving. In a world of rich-looking neutrals and unoffensive accessories (not that I don’t love a straw bag!), honestly, what a treat to see even classic looks injected with some personality—unexpected, twisty details that are just a little off-beat and seem to exist solely to save a look from being too tasteful for its own good.
It’s usually nothing wild or attention-seeking—just an unexpected sandal here, a curious earring there. But it added up to a city-wide vibe of charming irreverence, where the impulse to wear something joyful and a bit weird was winning out over playing it safe and appealing to the masses.
These quirky little winks aren’t for everyone, but that’s exactly the point. Maybe we’ve forgotten that it’s okay to wear a weird little anklet knowing that certainly isn’t “timeless,” but, perhaps, on an unremarkable Tuesday morning, it will peep out from under your work pants and make you feel a bit more like you? If weird little anklets aren’t your thing, here are five other entry-level ideas to stop your summer looks from playing it safe, inspired by the cool girls I spotted in Portugal.
Bright Red Sandals
A.Emery Remly Leather Sandals
Net A Porter
I promise you, there’s so much joy in wearing something a little unexpected south of your ankles. You don’t have to embrace the entire ‘Wrong Shoe Theory’—start with on-trend red sandals as a very easy way in. Yes, they’re the perfect punctuation to your white jeans, but the trick is not to let yourself wonder if they work with an outfit. If color makes you a wee bit nervous, just let these become your go-to sandals. Pretend you’re staying in a hotel room without a full-length mirror, throw these on with whatever, and get yourself out the door before you have time to overthink it.
Havaianas Top Sandals
Amazon
Something a Little Fishy
Hart Silver Fish Charm Lurex Necklace
Anthropologie
Again, let me remind you that the surprise and delight of a good outfit twist lies in it being an acquired taste. Much like actual sardines, fish-themed jewelry is simply not for everyone— and thank God, because if everyone wanted to be a sardine girl, we’d be bored out of our minds. I personally love a little jewelry moment that makes someone ask, upon closer inspection, “Is that an anchovy?” Why yes, Derek. Yes, it is.
Anni Lu Hippie Fish Earrings
Amazon
Embroidered Details
Sézane Marzia Shirt
Sezane
I am now firmly in the camp of believing that embroidery is the best way to jazz up a summer wardrobe staple. Classic button-down shirts, easy black pants, mini skirts, all just a little bit happier with a rogue flower or sun or palm tree—kind of like when you doodle on a fresh notebook in high school. I love my embroidered Sézane shirt so much (and get so many compliments on it) that I’ve just ordered a second one, so I won’t be devastated when I inevitably stain it.
Lspace x Rails Emmie Linen Embroidered Pants
Anthropologie
Crochet Tops
Madewell Crochet-Stitch Cotton Sweater Tank
Madewell
A summer wardrobe without a crochet top is really missing out. Even if you’re keeping colors simple, just the retro texture mixed in with classic summer staples (see the Madewell styling above) is enough to give you a little something. Maybe you’re just back from vacation, maybe you’re skipping out of the office early, or maybe you have an Etsy store. Let them wonder.
City Chic Cornelia Wave Openwork Top
Nordstrom
Unflattering Sunglasses
Eyeking Slim Oval Sunglasses
Anthropologie
Refer to all the earlier points about bright red sandals, and apply them here. Ask yourself, is it that those sunglasses don’t really go with anything—or, counterintuitively, do they actually work with everything? Also, I beg you, turn off the part of your brain that has been taught to care whether your sunglasses are “flattering”. Believe it or not, there’s no rule dictating that your eyewear has to complement your face shape or your outfit or anything at all, so venture outside of classic styles and colors. See what happens when you get as fun and weird as what makes you happy.
Elisa Johnson Aries Sunglasses
Shop Bop