How To Rock Your Most Boring Pieces — Tonight

When you're putting together your outfits — especially for those great nights out — you tend to have your favorite sartorial accomplices. That skirt meant for twirling, that shirt that sparkles in candlelight, or those shoes that turn you into Grace Kelly. No offense to your boring tees and trousers, but they're just not your first-draft pick.
However, if you've been feeling like your show ponies are getting a little too much time on the field ("You're wearing that feathered skirt again?"), it might be time to look at your trusty — albeit simple — standbys in a whole new light. With some clever styling and unexpected matchups, you can Cinderella-fy your most basic of basics. Don't believe us? Click through to see our tips — and don't be surprised if you find tonight's outfit in the mix.
Fancy-Bar Hopping — You may not think to reach for your most casual, everyday staples for a forecasted crazy-fun night out, but your favorite oversized gray tee and unassuming comfy pants make sense. And, guess what, they work well together when teamed up with other unusual suspects. Add a pair of stark-white dress heels (yep — you may have to dig them out from the summer storage bin) to your gray-tee/dark-pant combo to contrast against the neutral/dark color palette. Bring it all together with bits of cheeky bling, like mismatched earrings or even a chunky, shiny man-necklace courtesy of Dad or a stylish dude-friend. Or, score this one from Marc by Marc Jacobs for just $24!
Assembly New York Long Sleeve T-Shirt with Tux Stripe, $148, available at Assembly New York; Babaton Blake Pant, $145, available at Aritzia; Alexander Wang Maria Haircalf Peep Toe Mules, $795, available at Shopbop; Marc Jacobs ID Chain Necklace, $24, available at Marc Jacobs; Fiorelli Port Clutch, $89, available at Dorothy Perkins; Bing Bang Initial Heart Duo Studs, $48, available at Bing Bang.
Dinner And...Date — Excuse the ellipsis; it's not what you think. A "dinner" is when you start the night off with the set plan of dinner but never quite know where you're going to end up. Which is a good thing. It's the perfect occasion for those wear-them-everywhere, I-love-you-'til-eternity, black booties that never leave your feet. But, before you reach for your go-to indigo skinny jeans, opt for your tried-and-true, dressy pencil skirt. Sequins + comfy boots = "I am ready for fun, and it won't stop at this dinner." Pair it with a good, ol' trusty chambray shirt to bring it on back to your comfort zone. Add on the one piece of jewelry that gives you all sorts of happy feelings, close your eyes, pick a patterned scarf, and you are ready to face the elements whatever and wherever that may be this evening.
J.Crew Classic Button-Down Shirt In Dotted Chambray, $64.50, available at J.Crew Factory; Unique Sequin Pencil Skirt, $495, available at Topshop; Monki Leonar Heeled Chelsea Ankle Boots, $62.29, available at ASOS; Reece Hudson Siren Mini Bag, $495, available at Shopbop; Wanderluster Freia Ring, $45, available at Wanderluster; MIR Grey Multi Print Cashmere Scarf, $79.20, available at Bluefly.
Midnight Movie Night — This is the type of laid-back, Saturday-night activity that is begging for you to wear all your "boring" clothes at once. So, who are we to stop you? You are encouraged, and we're here to empower you. Boyfriend jeans? Check. A pair of slick gym shoes? Check! Sharp, black moto jacket layered over a super-light and comfy puffer? That's right. It takes a soft, sporty piece paired with an edgy, tailored piece to create the perfect outfit. Think: a peplum top and a structured, top-handle bag to stash your store-bought movie contraband. The ladylike closet basics juxtapose nicely with your relax-and-kick-back staples, so wear them well and do them right tonight!
Mango Zippers Leather Biker Jacket, $359.99, available at Mango; Uniqlo Ultra Light Down Jacket, $69.90, Uniqlo; Opening Ceremony Low Top Sneakers, $300, available at Opening Ceremony; J.Crew Peplum Ponte Top, $49.50, available at J.Crew Factory;Rafe New York Bryn Rivoli Dowl Satchel, $495, available at Bloomingdales; Tom Binns Safety Pin Bracelet, $290, available at Far Fetch; Zara Ripped Boyfriend Jeans, $59.90, available at Zara.

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