As long as you're not taking your date somewhere with a strict dress code, jeans are perfectly acceptable to wear on a first date. In fact, unless you're meeting in a formal environment, the easy-going denim look may be preferable. However, not any old pair of jeans will do. Go for a dark wash and avoid anything too trendy, like strange dyes, bleaching, or patterns. A dark wash conveys sophistication and inherently looks more expensive. Also make sure they aren't too big. Baggy jeans that repeatedly slide down look sloppy and clueless. Get the correct size, and when in doubt, select a style with "straight leg" in the name to avoid bulk and bagginess. Don't worry, straight leg is not the same as skinny (which would be a style risk for a first date, and, I suspect, not at all of interest to you).
If you don't want to blow your budget on jeans, try the Men's Mossimo Conner Straight-Leg Jeans ($24.99, Target) or these Men's Straight Leg Jeans ($14.95, Old Navy). Also, check out Aeropostale's denim sale, which takes 50% off all jeans.
However, if you don't mind spending most of your $100 budget on a new pair of jeans, these Low Rise Straight Fit Jeans ($78, The Gap, pictured) are perfect. They're casual, but because of their quality, style, and reasonable fit, they scream, "I know how to take care of myself. I'm reliable. I'll feed your cat when your boss keeps you late." Solid.
The majority of your efforts will probably go into what you wear on top. At times, you may think you look overdressed. You won't be. If you're wearing jeans, you will never be too formal for a first date. Stick mainly to sweaters, button-downs, and blazers. Old Navy does quality sweaters on a budget quite well, but this Striped Crew Neck Sweater ($25, Old Navy) is particularly great because it has some visual interest. Wear it over a tee or collared shirt. Also from Old Navy is this Classic Dress Shirt ($18), in 10 different prints. Keep the sleeves rolled up for a laid back look. Or, wear a tee under a casual blazer. But keep in mind, there are some things to avoid when selecting a tee: store logos, "funny" phrases or motifs that border on offensive, and anything that was handed out for free at a sporting event. Instead, solid or graphic print tees — like this Jerzees Tee or this "Tell the People" Mimic Tee (from $5, Target) — are safe options. Top it all off with this Corduroy Blazer ($44.50, Old Navy, pictured), which adds structure to your frame. In fact, if you're self-conscious about your mid-section, any of the above would look fantastic under a blazer.
Here's a directive you may not be familiar with: accessorize! Look like a well-groomed suitor instead of a forgettable clone by adding a bit of pizazz. Or, you know, a nice watch. A belt and nice shoes also work wonders. Think of these items as a period at the end of a sentence; they complete the look. In particular, guys tend to forget about footwear, which is a grave error. You may think to yourself, no one notices my shoes. But consider for a moment who you're trying to impress. I probably bought more shoes in the past three months than you own period. Women notice. So take heed: don't finish off your suave outfit with a pair of big white running shoes.
If you simply must go with sneakers, Converse is the most acceptable choice. They convey style, while leaving you comfortable. Plus, they look so cool with jeans and a sweater, like you used to be in a band before you went corporate. We dig that. Though a pair of leather or John Varvatos Chucks are exceedingly hip, basic canvas will work nicely. The Converse Outlet (click "Shop", then "Converse Outlet") offers discontinued styles for as low as $18, while the Converse One Star line for Target (our link goes to Olive, $17.49; search for "men One Star Oxfords" to see more colors from $15-$30; pictured in blue) averages about $10 cheaper than comparable retail prices. There are other brands of sneakers that could pass, but any other in this price range probably won't look as pulled together. Plus, you might look too athletic, and thus likely to run away at any moment. Which might be off-putting for your date.
If you can manage taking the style quotient up a notch, consider a pair of loafers, which aren't as haughty as they sound. A simple loafer (or a slip-on, if that induces fewer cringes) is a happy medium between the informality of a sneaker and the fussiness of a dress shoe. If you're worried about coming across as too suit-like, opt for a dark brown. It's dashing in a "college professor on the weekend" sort of way, instead of being a severe black. Try these GBX 131312 Shoes in Cocoa ($64.95, Shoebuy.com) or the Skechers Term Leather Slip-On Shoes ($45.99, Overstock.com, pictured). Make sure to wear them with thin, darkly-colored socks. Bleached white gym socks will look ridiculous.
Finally, if you can't bring yourself to getting gussied up in any special way, at least make sure the clothing fits. The reason why a white T-shirt and jeans can look alluring on one guy and schlumpy on another is largely a matter of fit. If you show up swimming in an over-sized tee, you might as well tell her you didn't care enough about this date to change out of your gym clothes. A fitted tee (which is not synonymous with tight) on the other hand implies care and eagerness, not to mention the fact that the proper fit will shave weight off your frame. Just make sure everything lays properly on your body, without sagging or rumpling.
By now you may be wondering if your date is worth the hassle and expense. First of all, for shame! That's no way to go into a first date. Secondly, think of this outfit as an investment. You could wear it to every first date you ever have. Obviously, none of them have seen you in it before. It's a dating no-brainer.
—Lindsay Sakraida, exclusive to dealnews