How to Make a Great First Impression

By: Amanda Massi, Personal Stylist & Founder of First Impressions

Irish poet W.B. Yeats got it right when he said, “Love enters man through the eyes.” When you see a well-dressed person on the street, you can tell they take pride in their appearance.  It’s that level of self-respect that makes them attractive and intriguing, right? Those first few seconds are your moment to impress an unsuspecting love interest.

So, what would you like your first impression to say about you?

While having a polished look may not seal the deal immediately, it could help you snag you an initial encounter or conversation.  So, what will you wear to that second date wine tasting in Napa? Or a third date at your favorite local five star restaurant? You want to show your personality through the way you dress without having to say “Look at Me!”

As the founder of First Impressions, a personal styling company, I help clients work with the clothes they already have in their closet to achieve the look that they want. My personal mantra is that people should not go out and blow a month’s worth of pay on a new wardrobe. It’s all about working with what you’ve already got in your closet with clothes you know you’ll be comfortable in.  It’s all about individuality – the most important thing is making your look your own, and not simply borrowing someone else’s look.

1) Let’s start with a casual first date lunch with a gorgeous gal or handsome guy.

His: Go with a laid back, cool look that is understated while making the right statement. The staple tee: Choose a color that works with your skin tone and brings out those eyes of yours. Pick one that’s made of a quality fabric and isn’t see through. Wear it with a pair of tailored pants and your favorite everyday sneakers or boat shoes. From there, add accessories that are sharp, but subtle, like a slick pair of Ray Ban shades.

Screenshot 2014-09-04 20.22.56

Hers: It’s best to keep it simple on the first date, as you don’t want to look like you’re trying too hard. Start with your favorite pair of skinny pants that accentuate your legs. Add a printed, unstructured blouse with an interesting design detail. Glam it up with accessories like crushed velvet flats and a statement bag. Keep jewelry and makeup to a minimum so his eyes stay on your face with as little distraction as possible. Since, obviously, you woke up looking like this.

Screenshot 2014-09-04 20.24.10

2) Congrats – you made it to the next severals dates! You’ll now need outfits that will transition nicely between day to evening. You’ll probably be planning dates that actually require going out and doing something, such as wine tasting.  Check out the following:

His: Take it up a notch by adding a structured piece to the look. Start with a nice, lightweight sweater over a button down. The key here is fit! You don’t want to look like you’re swimming in your father’s clothes. Add a classic jacket that isn’t too bulky and works as a layering piece, but is optional. Because it’s always beneficial to just happen to have an extra jacket handy when your date gets chilly later on. Pick a pair of pants that are comfy and tailored. Don’t be shy about using a slight cuff to show off your cool printed socks and sweet Allen Edmonds suede oxfords. It’s all in the details, and wine tasting is the perfect opportunity to make a little funky with colored accents.

Screenshot 2014-09-04 20.25.15

Hers: You want to look elegant but not overdressed. A printed maxi skirt says that you’ve got the confidence to play with different looks and aren’t married to skin tight body-con items. Wear a simple tank and boho inspired jewelry, then rough it up with a leather jacket. When it comes to shoes, wedges are great because they’re easy to walk in and they will keep you from tripping over your skirt after a few too many Pinot Grigios.

Screenshot 2014-09-04 20.25.55

3) You’ve gotten to know one another a little more. After that last rendezvous, it’s time for a fancy dinner followed by a spontaneous dance party at the local pub.

His: Keep it dressy but not uptight Monday-Friday dressy. Wear your favorite, impeccably tailored navy blue suit and a powdered blue dress shirt. Leave the top button undone because a little skin isn’t hard on the eyes. A pocket square will add that little extra detail that seals the deal. When it comes to the shoes, go with a low-soled loafer and don’t forget a slim pair of dress socks.

Screenshot 2014-09-04 20.26.33

Hers: It’s your chance to glam it up and totally knock him off his feet. Keep it classy with a form fitted, long sleeve dress that has subtle detail in color but simple design. Add a statement clutch that is easy to hold or carry under your arm. You don’t want to have to sling it over your shoulder during your impromptu dance session later on in the night. For jewelry, wear vintage-inspired earrings that are elegant and don’t scream costume jewelry. Go with heels that elongate your form like pointed black pumps, but make sure you’re able to walk comfortably in them. You’re a pro, remember?! You can dance in these babies all night!

Screenshot 2014-09-04 20.27.23

I hope that the looks I’ve shared with you have given you a little bit of inspiration and confidence to try out some new, fashion-savvy looks for your next date. Remember: it’s about being the most confident version of yourself, and feeling amazing in the clothes you already own. If you’d like more fashion tips or are interested in learning more about First Impressions, you can reach me at  

Leave a Reply

Your email address will not be published. Required fields are marked *