How to Dress for a First Date

When it comes to dating, a lot of women are completely clueless about what to wear. Here are my five biggest pieces of advice to help you make the right first impression.

MORE: 5 Things You Should Never Do on a First Date


Fit is the Essence of Style!

The first thing you should consider when choosing an outfit for any occasion is fit. Clothes that are too small actually make you look bigger, and clothes that are too big make you look sloppy. You don’t want to look like you’re popping out of your dress because you unexpectedly gained 20 pounds— nor do you want to look like a total schlump . Strike a balance by choosing the right clothes for your body type and if you’re not sure about fit, consult a tailor. Contrast Pencil Skirt, $90;

MORE: Clinton's Style School: Fashion, Fit and Style


Apropos or No

Appropriateness is another key ingredient for good style. On a first date, you should look like you fit in at the time and place where your date is meeting you. It shows that you are savvy enough to be comfortable in any locale. For example, if you’re meeting for coffee, jeans and a sweater would be more appropriate than a halter mini dress (this goes for hair and makeup, too). Instead of standing out as over- or under-dressed, you just want to look slightly better than everyone else so your date thinks, “Oh wow, what a catch." Pink Sweatshirt, $60;


Be the Best Version of Yourself

Look, I believe you should put your best self forward everyday, not just on a first date. That said, it’s important to be who you are as a person. If you wear dresses on a regular basis, then wear a dress that makes you feel beautiful and confident on your date. If you’re a jeans and t-shirt girl, but wear a dress on your first date, you’re telling your date that you wear dresses. That’s a bait and switch. You’re better off topping that t-shirt with a great jacket and killer booties instead of pretending to be something you’re not. Faux Leather Moto Jacket, $128;


Work What You’ve Got

If you have the money to buy something new, then go ahead! But it’s ridiculous to think you need a new outfit for every coffee date. Instead, shop your closet and use accessories to make things feel fresh. Add a red shoe to the pink dress you always wear with flats, invest in a new statement necklace, or try throwing on a jacket. Most people have mix and match wardrobes and don’t even realize it. Just be sure your clothes are clean, fit well, and that you feel great in them. And remember, everything’s new to your date! Tegan Tunic, $158;


The Shoe Sets The Tone

I always say there’s a reason why strippers wear stripper shoes and nuns wear orthopedic shoes: Your choice of shoe tells the world a lot about who you are, more so than anything else on your body. Whether it’s a combat boot, a flip-flop or a stiletto, a shoe has a personality all its own. Make sure your shoe is sending the right message and be sure it’s appropriate! If your first date is a glass of wine on a boardwalk, you might look ridiculous in a heel. Try a flat metallic sandal instead and not a rubber flip-flop. Kitten-heel pumps, $25;

Happy dating!

How to Dress for a First Date

#fbf to 1994 (ish) with my buds, @richardwiese and @wendirogerstv Bought that sport coat on sale for about 20 bucks because that’s all I had in the bank. Was 10% wool and 90% “other.” Got caught in the rain with it and smelled like wet dog ass all night.

Nine years ago, I made a vow to live my life based on three guiding principles: Love, Awe and Gratitude. Today, instead of feeling sad, angry or anxious about The Chew’s cancellation, I will look through the lens of Gratitude and thank: My cohosts, @chefsymon and @carlaphall, for being two of the greatest people I’ve ever had the pleasure of knowing. The crew and staff of The Chew for being so dedicated, hardworking and collaborative. Our viewers for allowing us into your homes each day to share a laugh and a recipe — and a cocktail. It’s been a fun run and I am so freakin’ lucky to have been a part of it. Much love, CK ❤️

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