Diving Back Into Dating? What to Wear on Any Date

December 18, 2015

If you're jumping back into the dating scene after some time off, you're probably wondering what on earth to expect. Times have changed, but one thing will always be true: A great outfit will boost your confidence and send you into any situation feeling and looking your best. 

If you're having trouble choosing an outfit for a first (or second!) date, try narrowing your choices with these tried-and-true suggestions. I've arranged them starting with the most casual, so you can find the right spot on the continuum. If you're not sure where your date falls (or if it's a surprise outing), I always think it's best to go a step more formal than you think you need to — but keep comfortable shoes in a large handbag or in your car for a quick change.

The Outdoor Date

Your outfit will vary based on the activity and the weather, but it's always fine to wear jeans on any adventurous outing — just not the ones you use to clean out the garage.

Even casual clothing should fit perfectly, and it's best to choose items with a little stretch for comfort. Wear a comfortable top and add a sweater or cute, fur trimmed puffer vest or jacket — layers are a good idea to keep comfortable the whole time. Choose shoes based on the activity, and make sure you have cute socks to show off if you end up taking your shoes off to change into skates or other special equipment.

The Casual Date

For an indoor trip to a play, art gallery or a quick meal at a coffee shop, start by being yourself. If you're a girly-girl, wear a skirt. If you normally dress for comfort, wear slacks and your most fabulous pair of flat boots instead.

Once you've chosen the "security blanket" portion of your outfit — a favorite piece that makes you feel gorgeous every time — plan the rest of your look around it, but give it a stylish boost. Add a tailored blazer left casually unbuttoned over jeans, or dress things up with a great new scarf or necklace. Sticking to one layering piece and one signature accessory (blazer or cardigan, scarf or necklace) will keep things clean and casual.

The Dressy Date

Dinner at a fancy restaurant is actually the easiest kind of date to dress for because you get to wear a dress! If you already have a favorite knee-length dress, wear it. If not, it's time to get one. You'll feel sexier and prettier in a dress than in a slack.

Choose a dress that flatters your figure — a wrap dress is always a great choice — in a color that complements your skin tone. Leave loud patterns alone. Accessorize your look with a sparkly necklace, earrings, and heels. Changing accessories gives dresses you already own a second life. Leave your big handbag at home this time — a small clutch or shoulder bag is enough to hold your phone and lipstick without detracting from your look.

One final tip? Smile! It's a major part of your style, and it works with every outfit. After all, dating should be fun — especially when you're dressed for the occasion.

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