The time-honored tradition of laughter and relaxation with your best girlfriends or your go-to coworkers after work is one that’s filled with camaraderie and a chance to finally unwind. It’s been a long day, and this is your time to celebrate life’s simple joys.
As you’re heading out to your treasured local haunt or the next hot rooftop bar in town, you might be wondering what exactly you should wear. Check out our guide on nine outfits to wear to happy hour and what shoes to pair them with to help you make a bold yet effortlessly chic fashion statement wherever the cocktails are calling you.
The Classic Cocktail Dress
Few outfits are as classic as the little black dress. This classic cocktail dress can be dressed up with heeled sandals and statement earrings. Finish off the look with a tailored blazer for a sophisticated touch. Alternatively, try a chic sheath dress with black pumps and a sleek clutch bag for a contemporary twist during your next happy hour.
The Cool and Casual Denim Look
The cool and casual denim look goes great with comfortable wedges. Wear well-fitted dark jeans with wedges and a stylish blouse. For a little edge, put on a leather jacket over your blouse. Alternatively, try a tucked-in graphic tee with high-waisted jeans and stylish sneakers. Accessorize with altered necklaces, hoop earrings and a crossbody bag with fringe details. This look is perfect for any cool and casual happy hour.
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The Retro-Inspired Look
Transport your happy hour look into a totally different era. Get a vintage look by going to a local thrift store or vintage shop to get a fit-and-flare dress. Put on a pair of Mary Jane pumps and accessorize with pearl earrings and a vintage clutch. For added flair, do your hair in an updo and tie in a hair scarf.
The Boho-Chic Maxi Dress
To get that laid-back boho-chic look, wear a flowy printed maxi dress with strappy sandals. Accessorize with layered bangles and add on a wide-brimmed hat. Alternatively, try a pair of ankle booties and a fringed bag. The bohemian ensemble is a great choice for an outdoor happy hour at a brewery or local pub.
The Tailored Blazer and Pants
For a dressier happy hour look or one that will take you from your cubicle to cocktails, pair a tailored blazer and pants with pointed-toe pumps. Tailored trousers or wide-leg pants look great with a simple camisole and a well-fitted blazer. Accessorize with a sleek watch and delicate stud earrings as you complete the look with a structured handbag and silk scarf.
The Effortless Jumpsuit
Fashion experts share that there are a few essential tips to keep in mind when you’re styling a jumpsuit. You need to find the right style and fit for your body type. If this is the first time you’re getting a jumpsuit, it’s best to start out wearing a black jumpsuit for easy styling and to bring shoes like flats or high heels with you to test out which looks best. You’ll also want to consider accessories like bracelets, necklaces and belts. Overall, the effortless jumpsuit look is one that can get you enjoying happy hour well into the evening. Wear a chic jumpsuit in a solid color with block-heeled mules. Add on a statement belt and hoop earrings to finish off your happy look.
The Casual Sweater and Skirt
For a chill happy hour look, especially on fall and winter evenings, combine a skirt and sweater for something warm and comfortable. A cozy sweater or turtleneck pairs perfectly with an A-line midi skirt and knee-high boots. Layer up with leggings or thick tights underneath your skirt for additional warmth. Complete your look with chunky bracelets and a crossbody bag.
The Monochromatic Power Suit
Want a look that’s sure to turn heads when you walk into your next happy hour? The monochromatic power suit is the perfect work-to-happy-hour transition as you take your tailored pantsuit in a bold red or an understated off-white with pointed-toe heels. Wear a silk camisole underneath the power suit’s jacket for a modern twist, and accessorize with a sleek clutch and red lipstick.
The Edgy Leather Jacket
To help tone down the powerful, edgy leather jacket, pair it with comfortable booties for women. Otherwise, putting this look together is easy for anyone who wants an edgier look for happy hour. Wear a graphic tee with a stylish leather jacket and studded ankle boots. You can swap the ankle booties for combat boots if you’re planning on drinking outside or want something with a bit more attitude. Accessorize your edgy look with statement earrings and a choker necklace.
No matter what you decide to wear, remember that your style should make you feel comfortable while radiating self-confidence. It’s about more than just the cute pair of comfortable sandals you’re wearing. Dressing for happy hour success also means putting on an attitude of enjoyment and fun so you dress to impress while expressing your unique self. Cheers to happy hour, where your fashion is sure to meet curated cocktail flavors!