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What To Wear On A First Date

Let’s face it, first dates can be nerve-racking. Although you can’t pre-plan conversation, you can pre-plan the perfect date night outfit! With the right outfit you’ll be sure to exude confidence the second you walk out the door. The trick to the perfect date night outfit is simple; choose your favorite part of your body and emphasize it!

Let’s start with those of you who have long legs meant to hit the runway. The best way to emphasize your legs is to opt for a shorter hemline and a nude shoe. A nude shoe, especially with a pointed toe, will elongate your leg and draw the eye up. This is also a great way to

create the illusion of longer legs if you’re on the shorter side like me. The perfect outfit to show off your legs would be a mini dress with a pair of pointed nude heels.

Now I’m sure some of you are thinking, “It’s post holidays, I don’t have a favorite part of my body!” If you fall into this category try to pick a top that shows off your back or clavicle. Off the shoulder tops and open back tops paired with dark jeans and heels is an easy way to conquer a sexy, yet casual outfit. This is also a great outfit if you’re unsure about the ambience of where you and your date are headed.

Lastly, we can’t forget about showing off your arms. If you fall into this category opt for a sleeveless maxi or midi dress with a slit. The slit will allow the dress’ material to move with your body, instead of clinging to your hips. Add a fun heeled sandal, and just like that you’re ready to go! This is a great outfit for a casual day date.

When planning out your first date outfit, the only way to go wrong is to not feel confident in what you’re wearing. When you choose to emphasize a part of your body that makes you insecure, you’ll be distracted from your date. Prepare for what you can control and make sure you feel beautiful from head to toe!


About Caitlin Jaymes, Celebrity Stylist: With a background ranging from Fashion PR to Fashion Design, Caitlin has found her love for closet organization and personal styling. With each client's individual needs and requirements in mind, Caitlin efficiently utilizes your space to create a perfectly organized closet that fits your lifestyle. After working with Caitlin, your newly organized closet will feel like LA's hottest boutique. Your closet is where you begin each day, so start each day stress-free! You can find Caitlin at @Caitlin_Jaymes on Instagram or

About Matchmakers In The City: MITC Matchmakers In The City is a top certified personal matchmaking firm in Los Angeles, New York City, San Francisco, and Washington, DC founded by a Matchmaker behind MTV's Are You The One. We are an old-school Matchmaking firm with a modern understanding and work with successful men and women who are looking for committed relationships in an offline, confidential experience. Our team provides an in-person, all-inclusive, private matchmaking experience with background-checked matches, concierge date planning, date feedback meetings, one-on-one date coaching with our celebrity experts and Matchmakers, and an 8 out of 10 success rate that we work hard to maintain. With no online public profiles or computer algorithms, Matchmakers In The City brings back the human element of dating. Visit to get started.

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