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Finding the perfect outfit for a date can seem like a daunting task. However, if you consider the season and the activity, you’re halfway there! Choose an outfit that fits well, is age-appropriate, and represents your unique style. Add a great pair of shoes, a few simple pieces of jewelry, a handbag, and a smile and you’ll be ready to enjoy your date.

Part 1
Part 1 of 3:

Considering the Occasion

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  1. Is it going to be warm and sunny or cold and wet? Look at the hourly weather report for the time you expect to be gone on your date. This will help you know what kind of clothes to wear as well if you may need additional items, such as an umbrella or sunscreen.
    • For warm weather, wear something in a lightweight, natural fabric like wool, cotton, pima cotton, or silk. For instance, you might wear a cotton sundress with cute sandals or a pair of shorts and a flowy top.
    • For colder weather, you could choose a nice pair of jeans or dress pants. Adding a printed blouse and a nice jacket, such as a pea coat, would take your look from everyday to dressed up.
  2. If you’re uncomfortable due to the weather or temperature, you won’t enjoy yourself. Whether it's layered tank tops, a blouse over a long sleeved tee, or leggings under a short dress, layers always work. Bring a wrap or jacket in case you get chilly. [1]
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  3. An active date requires clothing you can move around in. If you’re planning to go mini-golfing, choose a comfortable shoe rather than a high heel. If you’re going to a fancy restaurant consider a dress or pants with a nice blouse, rather than ripped jeans and sneakers.
    • For an active date, consider nice shorts, capris, or pants; a skirt or dress may make it more difficult for you to move around in. Pair your bottoms with a fun top; an off-the-shoulder blouse or a patterned tank top would work well.
    • For a date at the movies, a restaurant, etc. you could choose a skirt or dress. Consider pairing your skirt with a sparkly tee or ruffled blouse. Adding a fun jacket or shrug over your dress is also a nice idea. A romper would also work well for this type of date.
  4. Don’t wait until the last minute to choose your outfit. Think about what you might wear a few days before the date. You can even lay out your options and consider what you will feel the best in. That way, when the time comes, you’ll be comfortable and confident.
    • You could lay out several types of outfits: a maxi dress with a bold belt and sandals; fitted jeans with a ruched top and boots; capris and a wrap top with heels; a skirt paired with a graphic tee and flats; or a sundress with a jacket and wedges.
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Part 2
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Dressing for Confidence

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  1. If you are constantly pulling down your top or tugging up your skirt, you won’t be comfortable. Choose an outfit that fits well, meaning there are no bulging seams, puckering necklines, or uneven hems. As a general rule, if you wear a tight skirt or pants, pair them with a loose-fitting top. If you choose a tight top, pair it with looser pants to balance your look. [2]
    • If the weather is hot, avoid wearing tight clothes that will constrict you. Instead, wear something flowy and relaxed that will let you breathe and move.
  2. To determine your skin tone, look at the veins on the underside of your wrist. If they appear blue or purple, you have a cool skin tone and will look best in colors such as blue, lavender, rose, or gray. If they appear green, you have a warm skin tone, and will look best in honey, coral, olive, and cream. If it’s hard to tell one way or the other, you have a neutral skin tone, and will look best in jade, red, or white. [3]
    • A neutral top could be paired with colorful or printed bottoms, or neutral bottoms with a bold or patterned top.
  3. Don’t try to look like a thirty-something going out for cocktails. Wear clothes that are age-appropriate; nothing too tight or revealing. Consider classic styles, such as A-line dresses, fitted pants, and flowing tops. [4]
  4. Choose an outfit that makes you feel comfortable and that you consider awesome. Your date wants to spend time with you, not with you pretending to be someone you aren’t. Think about how you looked when you two made the date; start there and dress it up a bit. [5]
    • If you normally wear jeans and tees, don’t opt for an evening gown unless the occasion calls for it (such as a black-tie affair).
    • If your style is usually bohemian, for example, your date may be disappointed to see you in a preppy outfit.
  5. A smile is the best accessory there is. It tells your date that you’re ready to have fun and enjoy each other’s company. Keep a positive attitude. This will also help you seem more confident, even if you feel nervous. [6]
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Part 3
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Adding Accessories

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  1. A pair of shoes can change the way an outfit looks. Dress your outfit up with a pair of heels or boots, or dress it down with flats or sandals. Remember to keep in mind what you’ll be doing on the date and pick shoes appropriate for the occasion.
    • There are tons of options out there: wedges, stilettos, booties, kitten heels, pumps, slingbacks, platforms, peep-toes, and mules, or ballet flats, sneakers, flat boots, moccasins, oxfords, etc.
  2. Don’t go overboard here, two or three accessories are enough. A fun necklace or a couple bangle bracelets can give an old outfit a whole new feel. A scarf can add a pop of color to a neutral outfit, and a cute headband will really jazz up your look.
    • Fashion designer Coco Chanel advises women to look in the mirror before leaving the house and to remove one accessory.
  3. Remember that less is more here! One, or at the most, two, spritzes of perfume will do. Too much perfume is off-putting. One spray, a few inches over your head, will give you a nice, mellow scent. If you want to add more, opt for a light spritz on the insides of your elbows. [7]
  4. You’ll likely have a few items you’ll want to bring; keys, phone, cash, etc. Choose a clutch if you’ll have somewhere to set your bag, or a purse with straps if you won’t. Don’t worry about matching the bag to your outfit; you can coordinate them or choose a bag that contrasts. [8]
    • Women tend to dress better than men for dates. Everyone should dress for it, but not overdress for the occasion. [9] [10]
    • A guy can wear a cool pair of jeans and a shirt that has been washed and not just pulled out of the laundry pile. You do not need to wear a tie. [11] [12]
    • A woman should not show off too much skin. You can wear a revealing top and jeans or slacks, or a short skirt and a top that covers you properly. [13] [14]
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      1. Lisa Shield. Dating Coach. Expert Interview. 13 December 2018.
      2. https://theeverygirl.com/what-to-wear-on-a-first-date-we-asked-the-experts/
      3. Lisa Shield. Dating Coach. Expert Interview. 13 December 2018.
      4. https://theeverygirl.com/what-to-wear-on-a-first-date-we-asked-the-experts/
      5. Lisa Shield. Dating Coach. Expert Interview. 13 December 2018.

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