Avoid wearing anything you can’t walk, eat, or breathe in—you’ll be more confident when you’re comfortable, and your date will be sure to notice! Casual daytime settings These are great options for lunch, afternoon coffee, or dates at the park, museum, farmer's market, mall, library, or recordstore. Maxi dress + sandals This will highlight your arms and your décolletage. Blazer + shorts + sandals or low heels This is a classy, sophisticated (yet casual) look that will show off your incredible legs. Peasant top + denim skirt + sandals This is an easy going, delicate look that shows you’re a go-with-the-flow kind of girl. Long sheer cardigan + fitted top + jeans or capris + flats This is a no-fuss outfit best for outings that might require some walking (like going to the park or a museum). ⇒ Dress up these looks with heels or wedges to transition from daytime to nighttime casual. Men's looks Button-down shirt + jeans + sneakers Make sure your shirt is ironed and your shoes are clean for a casual but presentable look. Graphic tee + cardigan + jeans + boots or sneakers Pair a funky tee that shows off your artistic side with a cardigan and some clean, comfortable shoes. Casual nighttime settings These looks are ideal for casual dinners, movies, concerts, and informal parties. Cropped jacket + fitted t-shirt + skinny jeans + pointed-toed booties (or heels) This is a casual, fun look that can be a little edgy (with a tattered band t-shirt) or easygoing (with a fitted V-neck). Denim jacket + blouse + midi skirt + low to medium heels This semi-casual look expresses comfort, femininity, and class. Head-to-toe black + statement jewelry + neutral colored heels This is a refined, minimalist look that suggests a hint of mystery. Use a statement accessory (a necklace or bracelet) to keep it fresh and fun—just keep it simple! Belted mini-dress and sneakers or loafers This look will show off your waist and legs while giving off and easy-going, part-time-tomboy vibe. ⇒ Choose colors and patterns that flatter your complexion and shape. Avoid anything too trendy as it may seem like you’re trying too hard to impress. Men's looks T-shirt + blazer + jeans + loafers Pair a nice casual tee with a fitted blazer to class it up a bit. Wear dark-wash jeans and nice shoes to appear casual with a touch of finesse. Button down + bomber jacket + jeans + boots (or nice loafers) Choose colors that flatter you, and if you wear a belt, make sure it matches your shoes. Wear the button-down untucked or do a full or half french tuck (one side of the front tucked in while the other hangs loose). Dressy settings These looks are best for fancy parties, formal dinners, high-end art gallery openings, and other special events. Cocktail dress + heels Choose a color and fit that compliments your eyes and/or skin tone and shape. When it doubt, the little black dress is always a classic choice! Off-the-shoulder blouse + black fitted jeans + colorful heels This look will express your playful, creative side and show off your décolletage and shoulders. Slinky dress + structured trench coat + neutral colored heels This look is sexy, refined, and just the right amount of trendy for him to appreciate. Choose an eye-popping color for the dress (like red, green, or royal blue) to up the wow factor! Floor-length backless jumpsuit + heels This is a playful, statement-making look that exudes elegance and shows off your back. ⇒ Choose fitted, structured pieces for more formal events. Be careful not to show too much skin (a good rule of thumb: either show off your legs or your chest, not both). Men's looks Collared button down + tie + blazer + slacks + dress shoes Choose a fun pattern to differentiate between work and play. Add a pocket square to your blazer for an added touch of class. Black collared shirt or button down + patterned blazer + black jeans or slacks + black dress shoes Going all black with a patterned fitted blazer is a strong, classy way to make a statement. Feel free to throw in a vest for an added look of refinement (just make sure it’s either black or the same pattern as the blazer).