Last time we set the boundaries for what a first date outfit should entail. Remember, the look should reflect who you are, shouldnâ€™t give it all away (too tight, low cut, and too short are NO-NOâ€™S), shouldnâ€™t appear as though you tried too hard, and conversely, like you didnâ€™t put any effort into your look at all. The outfit I devised to meet all these guidelines included jeans, a flirty top, a blazer, and boots. However, this might not work for everyone — say, women who LIVE in dresses (as many of my friends do). A dress does not always have to indicate high-maintenance, and finding a dress you love and building upon it with fabulous accessories may result in that ever-so-elusive understated sexy, laid back, fun to hang with-vibe that is guaranteed to keep him transfixed by you. Just check out the look sported by Anne Hathaway!
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So, itâ€™s Friday night and the cute guy you met at a party last weekend asked you out on a date — you really like him and really want to overcome all the first date barriers to score an ever so elusive second date. Well there are lots of precautions to take to get there, but I will help you out with the first, which is perhaps the most important. You guessed it: Wardrobe Choice! Since this is a first date, letâ€™s consider a standard scenario: dinner at a restaurant whose ambiance falls somewhere in between local bar and 5-star hot spot, followed by a movie. The combo-date will give us a lot of leeway to examine several possibilities. Let’s look to Cameron Diaz for inspiration.
You could wear that killer dress that never fails to get heads turning. In this situation, however, a dress can potentially make you seem high-maintenance; while some guys do find high-maintenance gals appealing, itâ€™s a slippery slope, and a risk simply not worth taking on a first date. Slipping on a smashing dress, especially when combined with pre-date excitement, can also lead you to go way overboard with the hair, makeup, accessories, etc. — in which case you will have graduated from “too high maintenanceâ€™” to “total freaking drag queen”. FYI, that is a major first-date DONâ€™T!
You also could go the casual jeans and t-shirt route, you know, to show him that youâ€™re one of those cool girls who isnâ€™t obsessed with her appearance. Okay, true, he may find your laid back vibe appealing, however, if you put so little effort into this first date, it might make him too scared to stick around and see what future dates might hold. In other words, visions of unshaved legs might send him straight to the island of lost men. Let’s talk about smart options, after the jump. Keep reading »