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Are You Trying Too Hard? 5 Ways to Keep from Overdressing for Your Date

If you have a habit of overdressing for your dates, you may not even be aware of it. While there’s nothing wrong with keeping your outfit polished, certain style choices can push your look over the edge from classy to contrived. Being mindful of a few things and some quick tips will help you avoid making too grand an entrance.

1. Location, Location, Location

Researching both the general and specific setting of your upcoming date will clue you in to the most appropriate outfit for the occasion. Levels of formality vary from the East Coast to the West Coast, so especially if you’re new to the area, try to get a read on the natives’ style before deciding what you’ll wear on your date with a local. You’ll also, of course, want to adapt your look to your destination; don’t wear towering heels and a silk-chiffon dress if you’re meeting your date for a picnic—this will lead to more than one kind of discomfort.

2. Suits and Planners

Dating may feel like an interview process, but dressing in a power suit will kill the mood. We’re not saying you shouldn’t take pride in your career success and busy schedule, or that you can’t go straight from work to a date, but if you typically don a pinstriped three-piece for the office, wear a nice blouse or shell underneath and lose the jacket and vest before you get to the restaurant. (Check out the Work Attire section at myShape in the Date Planner for versatile desk-to-dinner outfits matched to your measurements and style.) And please don’t obsessively check your BlackBerry or pencil your next romantic rendezvous into your day planner in front of him. Telegraphing how in-demand you are will only make you seem self-absorbed.

3. Flights of Fancy

Even at a five-star restaurant, a satin gown with jeweled straps will usually be overkill (though all bets are off for the ballet or opera). The idea is not to literally outshine every other woman within a mile radius, but to let someone get to know you without getting upstaged by your ensemble. You might intimidate your date, come off as high-maintenance, or look like you’re trying to invoke Blanche Dubois, so save the couture for that white-tie wedding he’ll bring you to once he’s smitten.

4. Bling It On

Tiaras may have worked for Holly Golightly, but they’re downright preposterous on a date. Wearing expensive-looking jewelry signals that you have extravagant taste and will expect your partner to shower you with pricey gifts. Is this really the impression you want to create? If so, no problem. But in a down economy, flaunting wealth might be perceived as a bit tasteless and, depending on the circumstances, lead men to wonder if you’re a gold-digger.

5. Matchy-Matchy

Any outfit that’s too perfectly coordinated will show that you’ve spent a lot of time putting it together. Your date style should appear effortless (even if it took some planning) and place the focus on you rather than the clothes. You’ve probably heard that your handbag and shoes shouldn’t be the same color, but the same goes for your eye shadow and top, your earrings and necklace or your hat and jacket. In short: don’t show up looking like you fell into a bucket of paint.

When you visit myShape in the Date Planner and create a free Personal Shop, we can show you date-ready outfits that will flatter your figure and fit you well. (If you’re going for a flirty look, check out our Romantic Glam section for some fabulously feminine ensembles!)