A blouse and an A-line skirt
Show off this classic ensemble if you’ve got romance in mind. Wear a dressier top that really pops, like one that’s silk, floral, or ruffled. Go more low-key with your skirt and go for one tone like black, white, or navy blue. Skip the jewelry and focus on an earthy smoky eye and matte lips. Then, slide on some peep toe heels. If you have an A-line skirt with a high waist, tie a knot in a button-down shirt and show just a little skin. Studded ankle strap heels add a little bit of an edge if you want to go more punk. For flashier A-line skirts in floral or animal prints, wear a white or black blouse.
A sweater and a pencil skirt
This cozy set is great for a special, intimate evening. Grab a fitted or bodycon sweater, or tuck a looser one into your skirt. Accentuate your figure with any belt in a neutral color that cinches at the waist. Sling a small purse over your shoulder and try on sleek and shiny heels for a finishing touch. A cropped sweater and a knitted pencil skirt is great for cozying up on the couch. Try a mermaid pencil skirt and a bow blouse for an evening dinner date. If you two talked about cocktails and dessert, a leather pencil skirt will add to the flirty mood.
A sheath dress and a fitted jacket
If the atmosphere is sophisticated, walk in with this chic outfit. Wear a fitted jacket in a complementary color, such as a beige blazer with a turquoise dress. Add a statement necklace, like a layered chain or a geometrical design. Finally, throw on some pumps or slingbacks. To tone things down and go more casual, accessorize with a denim jacket. If you want to go more conservative, try a less fitted dress in the “sheath” style. If you’d like to be even more comfy, slide into some dress flats.
A belted dress
This versatile look works for a swanky or low-key dinner. Stick to simple jewelry, such as one pair of earrings or a set of bangles. Enhance your silhouette with shoes that accentuate your legs, like block heel pumps, ankle boots, or dress flats. If you want something really dreamy and sweet, pair a blazer and a dark belt with a lacy dress. Accessorize a shirt dress with a skinny belt and a matching purse for effortless charm. To go boho, cinch a maxi dress with a wide belt and throw on a statement necklace.
A blazer and a camisole
Look sleek for an upscale dinner he’s put together. Balance out the ultra seductive top with some simple jeans, like a straight cut or skinny style. Since a cami with a lacy neckline is so eye-catching, stick to just one bracelet if you want any jewelry. For a cowl neck top, wear a delicate drop necklace. Add a blazer in any contrasting color, then choose either neutral or statement heels. If you want to be a little cheeky, pair jeans and any blazer with a cami in an animal print. For a more tropical look, go for camis with fun designs, like a banana leaf pattern. To go more femme fatale, accessorize a white cami and black blazer with some leather trousers.
A flowy dress and a bolero jacket
Arrive in this if you’re going for a fresh and innocent vibe. Stick to a dewy, natural makeup style and try something new with your hair, like beachy waves or a high ponytail. Add neutral heels of any type and a pair of simple earrings. A dress in a gingham print and a pastel shade is a great, low-key choice for summer. A white or black dress pairs well with a bolero jacket in any color you prefer. If you ever want to remove your jacket, a dress with spaghetti straps gives him a fun surprise.
A floral top and jeans or a skirt
This gentle and feminine look is perfect for a casual night in. Throw one printed piece, such as a blouse, a dress, or even a skirt. Balance out a flowery pattern with bold, one-tone choices, such as dark jeans, a white jacket, or a plain silk blouse. Add a simple matinee necklace and slingback heels or ballet flats. Try a self-tie top with jeans or a skirt for a whimsical retro look. Wear a mid-calf floral skirt with a solid colored top for a creative take on the print. A floral leather jacket can add an unforgettable edge to any outfit.
A jumpsuit and heels
Make a power statement after a few first dates and go for something daring. Wear more understated jewelry, like a single bracelet, one statement ring, dangle earrings, or a dainty circle necklace. Finish your look for strappy heels or stilettos. For the best silhouette, the hems of your jumpsuit should stop at your ankles. Ribbon heels are a great way to add a romantic flair to any jumpsuit. A small clutch purse looks really charming to round everything out.
A peasant top and denim
Charm in this ethereal choice when he brings the date outdoors. Pair it with skinny or flared jeans, or tuck it into a denim A-line skirt. Add a creative and whimsical flair with a neck scarf, headband, beret, or wide-brimmed sun hat. Round out your look with your fave sandals, such as a flat, platform, or strappy style. Raw hem jeans give a peasant blouse a relaxed look and make you seem really at ease. If it’s summer or the weather’s warm, put on shorts to add a touch of daintiness to your peasant top. Choose one type of jewelry, like a bar or a chunky necklace, a stone bracelet, or stackable rings. Add a leather cord choker to draw his attention to your neck and tease just a little.
A cute top and jeans
Slip on this simple choice for any casual hang-out. Choose skinny fit, boot cut, or jegging styles for looser tops and straight fit, high-waisted, and flared jeans for tight shirts. Go for a small purse as well as flats, sandals, sneakers, or even pumps. Try a knit crop top and cardigan combo for a super sweet vibe. Throw on a turtleneck when it’s cold to stay warm and chic. Wear a bodysuit underneath your jeans for an extra fitted look.
A long cardigan, a thin top, and leggings
Come over for snacks and drinks in an outfit with cool swagger. Stick to dark leggings to keep things simple, then go for a high-low tank top, a silk tee, or even a lacy bustier. Pair it with a cardigan in a complementary color—for instance, a simple white tone matches well with an eye-catching red. Keep it casual with canvas shoes, or add a little elegance with dress flats. Use a French tuck with a T-shirt or tie the bottom in a knot to accentuate your figure even more. Ankle boots will bring even more attention to your legs when you wear dark leggings. For a look that’s both daring and feminine, pair black leggings and a white top with a floral cardigan.
A hoodie and skinny jeans
Chill and vibe together in this laidback look. Keep it really understated with a black hoodie and white runners, or have some fun with a really colorful hoodie and distressed jeans. Pop on some sneakers, combat boots, or platform sandals and you’re good to go. For a softer look, play with pastels, such as a light blue hoodie with a pink pleated skirt. Wear a tie-dye hoodie and ripped jeans for a cute vintage vibe. Swap out jeans for a plaid skater skirt and accessorize your hoodie with a choker or a leather cuff.
A cute activewear set
Be ready for any adventure with this comfy number. Go for a sporty crop top and high-waisted leggings or a colorful and fresh tracksuit. Add fun little touches, like a sweat headband, a cropped shrug, pullover hoodie, or crossbody pouch. Then, put on your favorite pair of kicks—anything from fresh white sneakers to neon trainers works. Wear a high ponytail to get ready for any games or sports you want to jump into. Accessorize activewear with printed socks to show off your fun-loving side. Wear simple jewelry that’ll stay in place when you move around Throw on some cool sunglasses if he’s planning a picnic or lunch in his backyard.
Cozy loungewear
Snuggle up to him in an adorable set for movie night. Go for a matching set, or mix things up with printed lounge pants and any fitted tee or tank top. Throw on a cropped hoodie if you get cold, and slide on some cute fashion slippers. For an extra touch, go a little heavier with your makeup just to have some fun and keep the look date-ready. Throw on cable knit shorts, a tank top, and a ribbed cardigan for a super soft set. Cut off an oversized band or graphic T-shirt to add some personality to your loungewear. Treat yourself to a fresh manicure and show it off with your fave slippers.
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