What and What Not To Wear On the First Date–From An Upscale Matchmaker

One of the biggest questions I get as an upscale matchmaker in Los Angeles is “What do I wear on the first date?”, it’s something every girl wonders, whether she is into fashion or not, every woman wants to look good for that first impression she will have with a man, I will also include what you might want to wear on a first date to make that great first impression.

Here are seven to consider not wearing on a first date:

Red Lipstick: As pretty and classic as it is, forget the red lipstick, its messy, it gets on your teeth and on his shirt. Instead try a red tinted lip gloss.

Very high heels or brand new shoes: Unless you are very comfortable wearing those 5” heels leave them at home, same with the brand new shoes that give you blisters. Wear shoes you are comfortable in, like a pair of ballet flats or low heeled pumps because he might want to take an after dinner or after lunch stroll.

Designer Bag:I’m talking about the designer bag with the logos all over it. This screams ” I’m high maintenance”, which is NOT usually the impression you want to give, since he has no idea it might be fake or you got it half off.

Uncomfortable clothing:Don’t wear anything you are not 100 percent comfortable in, that goes for anything too tight , too short or two low-cut.

Flip-Flops:  For the love of all that is holy, please don’t wear flip-flops on the first date, unless your first date is at a pool or the beach.

Leggings: One word: No.

Anything too Trendy: Guys don’t usually follow women’s clothing trends, so he might be a bit taken a back by that pair of harem pants you love. By the way,  Please don’t wear harem pants…ever.

Heavy perfume: When in doubt, go without. If you must, wear something light and airy.

Five To Consider Wearing on The First Date

Your little black ______: This could be your little black dress, your little black skirt, your little black slacks…anything that is classic that makes you look fabulous, a tried and true piece of clothing you look and feel great in.

Jeans: For a casual date, your best fitting pair of jeans does wonders paired with a blouse that flatters your figure. Try to go with a pair that best flatters your shape, i.e. probably not the time to wear skinny jeans.

A  statement piece: You have that one piece that always starts conversations. Maybe it’s a vintage brooch your grandmother gave you or a beautiful necklace you bought at a flea market in Paris–men love individuality and a great statement piece can start a conversation.

Minimal Makeup: Believe it or not, most men are not fans of heavy makeup, wear just enough to flatter your facial features, but not enough so that a man can see that you are wearing makeup.

Soft/Sleek/Feminine fabrics: Men love soft, cuddly fabrics like silk and cashmere.

Nicole is an upscale matchmaker at Perfect 10 Introductions.