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6 Foolproof Ways To Look Great On Your Next Date

Updated: Jul 26, 2023

by Gab Saper

I’m Gab Saper, a personal stylist based in NYC. I work with clients to build authentic, functional wardrobes that empower them as they enter the next stage of their lives – whether that’s finding love, getting a promotion, becoming a parent, changing careers or anything else.

In addition to being a personal stylist, I spent many years dating in NYC and have seen the best, the worst and everything in between with date fashion. I believe that a great date outfit makes you look like the best version of yourself while leaving room to let your personality shine.

First dates are about getting to know each other, seeing if there’s a spark. It’s hard to focus on meeting a new person if all you’re thinking about is if your hair looks good or your shirt is too tight.

A client who I worked with previously is the perfect example of this. He wasn’t confident in how he looked, and as a result wasn’t able to be fully present while on dates because he kept second guessing himself.

Follow these simple steps, and you’ll achieve the first-date confidence that you need!

  1. Know the dress code. The location of your date should dictate the formality of your outfit. White tablecloth restaurant? Dress it up. Outdoors? Keep it more casual. If you’re not sure, drop by the location of your date, or look it up on Yelp, and see what people wear when they go there.

  2. Know the formula. Jacket, shirt, pants, shoes, belt. This will never fail you.

    • Jackets

      • Formal: Blazer, leather jacket

      • Casual: Bomber jacket, cardigan

    • Shirts

      • Formal: Crisp button down

      • Casual: Solid tee or thin sweater

    • Pants

      • Formal: Dark slacks

      • Casual: Dark jeans

    • Shoes

      • Formal: Leather loafers, ideally with almond toes. Not too round or too pointy.

      • Casual: Clean, non-athletic sneakers. Bonus points for leather.

    • Belt

      • Belts should be the same color as your shoes. If you’re wearing white sneakers, wear a black or brown belt – whichever looks best with the other colors that you’re wearing.

3. Color. To make picking colors easy, keep your jacket and pants dark and your shirt light. When pairing darks, avoid darks that are close but not the same: black and navy, two different browns. Navy and brown is always a winning combination.

4. Fit. Clothes should fit well in size, proportion and length.

  • Your clothing should fit your body. Clothing that is too loose or too tight will not make you look thinner or taller, I promise.

  • Trends like super skinny and wide leg come and go. Keep proportions classic – right in the middle, not too wide or narrow.

  • If a sleeve or pant is too long, tailor it. No pooling hems or sleeves. If something is too short, don’t wear it.

5. Grooming. Shower, put on deodorant, shave or groom your facial hair, cut your nails, brush your teeth, floss and get a haircut if it’s been more than three weeks since your last one. This is more important than you think.

6. Scent. Apply a signature scent. Spray one spritz of cologne on your neck and one on your wrists.

Before you walk out of the door, take a look in the mirror to make sure everything is in place, and there is nothing in your teeth.

Remember, these guidelines are here to help you look your best so that you can focus on being yourself and connecting with your date.

Once you’ve picked out your outfit based on these guidelines, you can feel confident that you’ll look great, and pay attention to what really matters – the person who you’re meeting!

Back to my former client, he went on dates with many women where he felt there should have been a spark, and he kept getting rejected. After we revamped his dating wardrobe, the next woman he went out with ended up being his girlfriend in just a few short weeks. She later told him that she was attracted to how attentive and present he was on their first date.

Feel free to check out my website or Instagram for more on my services and me.


Gab Saper has been styling everyone around her since childhood. Gab founded Wardrobe Editor to turn that hobby into a career. She works with clients across many ages, genders and life stages to help them build wardrobes that empower them to live their best lives. Gab also loves styling clients for events including job interviews, vacations, photo shoots and weddings.

1 Comment

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