How to Dress on Your First Date

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Tue, Nov 11 - 9:00 am EDT | 4 years ago by
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Style Undressed - First Date

You want to be confident, comfortable and authentic when getting together with a woman for the first time. She wants to get to know the real you, so be genuine. On a first date, don’t dress poorly or too casual; that may be perceived as disrespect. And women definitely want to be respected and appreciated.

Even if you have a laidback, carefree personality, you should care enough to take the time to prepare (and even primp a little) before going out with someone new. No matter what you are wearing on a date, “all clothing should be clean, odor-free and wrinkle-free,” says Marian Rothschild, AICI FLC, certified personal image consultant and author of Look Good Now and Always.

Use common sense
“As a guy, the two things that are mandatory for a first date are cleanliness and confidence,” explains E.J. Thompson, a former DJ that had to make first impressions with women multiple nights a week as an entertainer. Thompson now runs an e-commerce clothing store called Jenny’s Posh Pickings. You want clothes that fit the occasion and you want them to fit your body type properly. You want confidence, but you don’t want to be the guy who’s wearing a suit that looks like your dad’s. Have some common sense. You need to break out the iron, you want your hair to be cut and put together correctly, and you must have clean and crisp footwear. “No woman wants to run around in public with some guy who looks like he just woke up or someone with dingy shoes. It doesn’t matter what kind of style you have, cleanliness is mandatory,” says Thompson.

Don’t ditch your denim
When you arrive at your first date, you want to make sure that you look polished right from the get-go, which can often be a challenge during the winter months with hats and gloves. A scarf can really pull an outfit together. This Caravaggio wool and silk men’s scarf makes outerwear look super sophisticated, and it’s woven and spun in George Clooney’s majestic hometown of Como, Italy.

If you’re a jeans and T-shirt kind of guy, then dress that way. Don’t go over the top because the woman will then expect that you’ll always dress extravagantly. If it’s fall or winter, for a casual date, wear a favorite sweater and dark jeans. If it just so happens you’re going to a symphony concert or other formal event, leave the tux at home. A nice jacket/pants/tie combo will do.

You can never go wrong with a good pair of jeans, says Jessica Murray of Project Fixup, a dating website based in Chicago. Darker washes look polished, and can be dressed up or down depending on the occasion. Make sure your jeans do not have any holes, frays or worn out patches. Keep it simple. Solid color or striped button-downs, sweaters or Polos are always good options to partner with denim.

Make sure it fits
Did you gain or lose weight recently? Is it a shirt you bought while in college? Be realistic about your body type and what clothing works best. Baggy shirts look just as bad as shirts with buttons that are about to pop, says Murray.

Accessorize – but don’t overdo it
A watch will keep you off your phone, which is a big date no-no. One accessory accent piece beyond that will complement your outfit and give a hint to your personal style. Once you take off your coat, a rugged but chic bracelet is a perfect accessory. Sophisticated and understated, the STEL black leather bracelet is perfect with a sweater or button-down shirt. If jewelry isn’t your thing, a unique hat, cool glasses or even an unusual belt buckle can add some flair to your look.

When the date ends and you’re ready to pay the check, make a great lasting impression with the Will Leather Goods Barnard billfold.

Clothes don’t make the man (or the date), but they sure do help.

Don’t miss last week’s column to learn what your shoes say about you. Also check out these first-date horror stories for lessons on what not to do!

Aly Walansky is a New York City-based lifestyle and travel writer. Tweet her at @AlyWalansky or visit her blog at

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