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What to Wear on a First Date: Outfit Ideas for Every Kind of Plans

It seems as if all your flirting has paid off—that boy you’ve been crushing on for, oh, forever finally asked you out on a date. Or perhaps you (wo)manned up and asked him out (major kudos, by the way). Either way, the date’s set and the plans have been made; however, the outfit is a work in progress. Though we can’t back this up with science just yet, we have reason to believe that nailing your first date outfit may lead to a great time (and maybe even a second date). But in a world where sporting a bodycon dress to a coffee date is out of the question, styling a sartorially superior ensemble is not as easy as you’d think. For this occasion, we asked both fashion gurus and collegents the million dollar question. And don’t miss the super cute and insightful infographic from Her Campus and We Love Dates for more tips about dressing for the first date!

Scenario One: Dining Hall Date

Between both of your busy schedules and an average college student’s budget, grabbing a bite at the dining hall is a viable option. So what do the experts have to say? “Colored skinny jeans with a simple top or sweater and cute boots,” suggests Kyle Alexandra, a fashion stylist. We adore Topshop’s Moto Jeans (Now $38)—they’re stylish, yet the bordeaux hue is subtle enough to be date appropriate. Since the jeans have loads of color, sport Romwe’s cozy white sweater ($43). As Alexandra mentioned, pair this ensemble with a polished set of riding boots ($33). For a finishing touch, jazz up this ensemble with silver earrings ($70)and a silver cuff (now $9). So what do the guys think of this look? “What you wore to class that day is fine,” says Andrew Bensch, a senior at San Francisco State University and HC’s Real Live College Guy. “It’s the dining hall after all, I wouldn’t read too much into it.” Even though a “just left lecture” look is probably okay with your date, we know you’ll rush to the bathroom to touch up your makeup, fix your hair and take a final look at that casual chic ensemble first.

Scenario Two: Coffee Date

Since this scenario is generally more casual than other settings, it’s important to sport a look that’s casual and stylish. “Totally cool prints make a statement and give your look style,” says Dawn Del Russo, a fashion and lifestyle expert and author of 101 Glam Girl Ways to an Ultra Chic Lifestyle. But before you whip out a paisley top, remember that collegents don’t like flashy. “A flannel shirt would do the trick,” says Ben Rader, a junior at Washington University at Saint Louis. Woolrich’s Pemberton Plaid Flannel Shirt ($29) makes a statement; however, it’s not in-your-face. According to Del Russo, tone down this printed top with a pair of black skinny jeans. “Show off those fab legs,” cheers Del Russo.

We love French Connection’s  ($62) take on this staple. Lastly, complete this look with gold accents: Bardot point flats ($53), Michael Kors Brilliance Pave Fireball studs ($75) and Brooks Brothers’ pearl cluster bracelet (now $84). Don’t be too freaked out if some random collegiette keeps eyeing your table—she’s probably just smitten with your outfit.

Scenario Three: Casual Dinner

 

You may not be going to your college’s dining hall, but getting a quick bite at a soup and salad joint is usually not fancy enough to warrant throwing on a luxe ensemble. So what should you wear? “I like when girls wear a sundress with a cardigan,” says Ben. Instead of sporting a cardigan, upgrade this ensemble by sporting a blazer—it’s sophisticated and chic at the same time. “Start tame with a blazer that comes off if he looks cute,” suggests Del Russo. We love Choie’s cut-out flower dress ($70) with a black boyfriend blazer ($48). As for the accessories, add a fun cocktail ring. “A cocktail ring is the [perfect] finishing touch,” shares Del Russo. This House of Harlow cocktail ring ($50) is super fun and chic. Tie the black blazer and gold ring together with a pair of two-toned flats ($65). This date may be casual, but you’ll look (and feel) like a million dollars.

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Scenario Four: The Movies

Just because you’re sitting in a dark theater doesn’t give you an excuse to sport anything less than amazing. For Evan Squire, a junior at New York University, it’s all about sticking to the basics. “Anything too flashy or extreme doesn’t seem like a good idea [for] a first date,” says Evan. Our style experts could not agree more! “[Try] a long cardigan belted at the waist, skinny jeans and cute shoes,” says Erin Murray, Alexandra’s style assistant. Since movie theaters can get a little chilly, pair a belted cardigan ($62) with Mint Velvet’s long sleeved shirt ($47). Keep the rest of the ensemble equally casual with a pair of Dorothy Perkins jeans ($49) and brown riding boots ($39). Last but not least, rock a pair of hoops—we are obsessed with Ralph by Ralph Lauren’s brass hoop earrings ($28). Comfortable and cute– we approve!

Scenario Five: Concert

tGet ready for a date that involves a lot of moving, sweating and shouting—a concert, obviously. Whether you are going out with a music fanatic or the two of you are obsessed with the same obscure band, before you plan your outfit, consider the venue and the act. Your new sweater may be sartorially superior, but you shouldn’t wear it to a crowded techno concert—that sounds like a nightmare. Concerts tend to get a little warm, so layer up! “Something fun and comfortable, yet chic, is key,” says Murray. For a perfect concert outfit, Murray suggests you throw a boyfriend blazer ($47) over Miss Selfridge’s sequined top ($68). According to Murray, counteract your top’s pizzazz with Levi jeans ($72) and a simple gold bracelet ($70). “Choose comfortable shoes,” insists Murray. These studded flats ($37) are practical and stylish. Don’t worry collegiettes, this ensemble will get the guy’s seal of approval. “Jeans and just a cute top,” says Andrew. “Nothing too fancy.” With a stylish, venue-appropriate ensemble, nothing can stop you from moving, sweating and shouting like a concert veteran.

Scenario Six: Getting Drinks

If you’re of legal age, getting drinks with your suitor is definitely a possibility—how adult of you! For this scenario, it’s important to dress like a dateable woman instead of some chick he can take home after a few too many drinks. “I do like when a girl wears a black dress,” say Mike Loffredo, a junior at Carnegie Mellon University. “It makes her look more sophisticated and mature.”  Ditch the bodycon silhouette and opt for a more classic shape. We love the full skirted dress from OASIS ($67) because it’s sexy and still says, “I’m dating material.” And according to Del Russo, the fitted waist is perfect for a date. Instead of stumbling in a pair of platforms, do the responsible thing and sport Lucky Brand’s gray booties ($97). Finish this look with a glitzy bracelet ($26), thick tights ($12) and a smoky eye. Though you’re in a laidback environment, remember to keep it classy. Doing otherwise will not only give him the wrong impression, it may also lead to a wardrobe malfunction.

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Scenario Seven: Fancy Dinner

Sport a sophisticated dress if the two of you are going to a more upscale restaurant (you know, a place where there’s bread on the table and nice cloth napkins have replaced your average paper ones). “Every girl should have a great wrap dress,” notes Alexandra. “Think Kate Middleton—a look with a silhouette that shows off a great figure without revealing a thing.” Phase Eight’s wrap dress ($110) is so classic, plus the dark green is super chic. Plus, collegents will go crazy for this ensemble. “I’d go with a knockout dress, something cut around mid thigh with zero cleavage,” says Andrew. “Sexy to me is leaving more to the imagination up top, but showing off the legs.” According to Alexandra, it’s important to give this dress some pizzazz with some amazing accessories—she votes great pumps, earrings and a chic clutch!  Michael Antonio’s suede pumps ($49) are the ultimate basic pair of heels, not to mention the slight platform will minimize any post-date foot pains. For a hint of sparkle, we recommend sporting White House Black Market’s Square Pave Earrings ($14)—this pair is glitzy enough without overdressing. To bring the whole look together, carry a black and silver clutch ($50). But this outfit is not complete just yet. “Spend some extra time doing your hair and makeup,” suggests Alexandra. Give your eyes the attention they deserve with a subtle smoky eye (we say subtle because you don’t want to look you’re going to the club after). If you’re completely a beauty novice, try using Benefit’s Smokin’ Eyes Kit ($36). We won’t be there to help you decide between the chicken and the pasta, but we just know you’ll be the best dressed collegiette in the room.

Scenario Eight: Date Party

Instead of dragging your GBFF along, try asking that cutie from your lab to be your date. It may not be the conventional date, but a date party is a great way to get to know your crush. But what should you wear? Contrary to popular belief, not all collegents are dying to see you sport a bodycon dress to this occasion. “A huge turn-off  for me is when a girl is wearing the tightest dress possible,” confesses Sean McFarland, a senior at the University of Pittsburgh and one of HC’s Real Live College Guys. “Some look like they were literally sprayed on. For some reason, it just comes off to me as trashy.” This strapless dress from John Lewis ($21) is fitted, but won’t make your date think that you’re suffocating. Plus, the peplum details add a stylish twist. According to Del Russo, add a nude shoe to this show-stopping dress. “It keeps this look chic,” claims Del Russo. We love Jessica Simpson’s Adeni heel ($56). To reach optimal glamour, accessorize this look with Banana Republic’s statement necklace ($90) and MANGO’s Metallic Striped Clutch (now $60). Not only will this ensemble wow your date, all of your sorority sisters will be gushing over your glamorous outfit.

Scenario Nine: Surprise Date

Though this wild card option seems quite unlikely, it happens. It all starts when you ask your date what the plans are. “It’s a surprise ;),” he texts back. “He’s spontaneous and cute,” you coo to your girlfriends. But your idyllic fantasies of this mysterious date come to a halt when you realize the terrifying reality: if you don’t know what you’re doing on your date, you can’t possibly choose an appropriate ensemble. Or can you?  “A pretty feminine top paired with a cool jacket and some skinny jeans with some fabulous boots or flats would be perfect,” says Alexandra. With a versatile outfit (as well as shoes that won’t kill your feet after a few hours), you’ll be equally prepared to dance the night away or go go-kart racing. For the ultimate surprise date ensemble, pair Oui’s lace shirt ($64) with this edgy jacket from H&M ($56). Keep the rest of your outfit simple with MANGO’s Silm Jeans ($25) and basic black flats ($59). As for the accessories, top off your look with some sparkle. “An earring or cool ring that twinkles would be perfect,” suggests Murray. A pair of black diamond and sapphire pyramid stud earrings ($14) provide just the right amount of sparkle.  This versatile, yet stylish, outfit is sure to be a hit no matter where you are.

While dressing to impress definitely won’t ruin your first date, the most important thing is to be yourself. If you’re trying too hard to impress a guy, chances are that he’ll notice. “I think the trick is to wear something that will make you feel comfortable in the environment you’re going to be in,” concludes Ben Bergstrom, a junior at SUNY Geneseo. “Because the key to getting a second date is being happy, open and comfortable with being yourself when you’re on your first date.”  Amen! 

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Looking for more tips on dressing for the first date? 
Check out this infographic from Her Campus and We Love Dates.

Kelsey is a senior at Boston University, studying Magazine Journalism  in the College of Communication. As a magazine junkie and fashion fanatic, she loves being a part of the Her Campus team! At BU, Kelsey is president of Ed2010 at Boston University.  She has interned for Time Out New York, Lucky, Anthropologie, and Marie Claire. Kelsey also has a fashion blog, The Trendologist, where she covers the latest trends, fashion shows, and red carpet reports. When she isn't busy, Kelsey loves hanging out with her friends and family, shopping, reading style blogs, going for a nice jog, listening to music, creating baked goods in the kitchen, watching movies, and eating tons of frozen yogurt and sushi! After graduation, Kelsey hopes to work as an editor for a fashion magazine. Follow Kelsey on Twitter and Instagram at @kmulvs and don't  forget to check out her "Catwalk to Campus" blog posts!
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