Look the place up online and find pictures to see how fancy or casual it is. Look for pictures with other people in them to give you an idea of how people tend to dress there. Swing by the place before you meet him so you can get the vibe in person.
Daytime calls for light or bright colors and a more casual style with less jewelry. You can still wear a dress, but tone it down to a simple shift, shirt dress, or wrap dress. Meeting at night means a more formal style like that little black dress with some heels and that one piece of eye-catching jewelry.
Make distressed jeans work for you by pairing them with a nice pair of black heels and a sweater or silk blouse. Combine an oversized shirt with something fitted like tights or leggings so your outfit doesn’t look baggy or ill-fitting.
Black leather jackets have style and class, and go with almost anything. They are a great addition to your wardrobe. Accessorize with a hands-free purse like a clutch or wristlet. These look more sleek and sophisticated than fussing with a large bag. If you need more space to carry things, use your jacket pockets.
Avoid heels which are incredibly high. Not only may they be difficult to walk in, but you might tower over him if they are too tall.
People who dress more formally tend to be perceived as smarter, and more successful. People with a more casual look come off as friendlier and more adventurous.
Try asking a guy friend so you can get a male perspective. Get more than one opinion, because your relationship to different friends can affect their perception of your outfit. Tone the outfit up or down, or change it entirely and start over based on your friend’s response.
If you are both really into music, you could wear a band t-shirt. Put on the necklace, bracelet or skirt you got overseas to show you are a free-spirited adventurer. Cowboy boots will give off the impression of a country, outdoors type. Doc Martens will set you off as more of a punk rocker.
Stick with your normal style rather than trying to change your look for the first meeting. You want him to meet the real you. You don’t want to look completely different if the two of you decide to hang out again.
Ask where he grew up. Certain regions have different styles. Someone from Brooklyn may be more on the cutting edge of style than someone who grew up in the country in Montana. Ask what his hobbies are. If he spends time in coffee shops and record stores, he is probably more of a hipster. Someone interested in sports is probably more of a t-shirt and shorts type of guy.
Think about what outfits you have gotten compliments on in the past. Choose comfortable clothing which fits well. You don’t want to have to worry about adjusting yourself all night.
Save the daring choices for a later date when you want to spice things up.
Stick to just some powder, blush, mascara and lip color. Avoid excessive eye makeup or bold lip color for the first meeting.
If he does spend a lot of money or time on his outfit, then he is probably just as worried about how he looks as you are.
