What To Wear On Any Date

woman selecting outfit from closet clothes hangers

Fashion for every dating occasion!

Gone are the days where a little black dress would fit the bill for any dating occasion. Before I got into the matchmaking industry 20 years ago, I worked in the world of fashion, so I can tell you with authority that it's a good idea to try and match the vibe of your date with the vibe of your outfit. Meanwhile, I've put together a basic list of five possible date destinations and the matching ensembles you should wear:

1. Casual. If your date is taking you somewhere casual and relaxed, put on a pair of jeans and a cute tee shirt. Jeans have become a lot more acceptable in the fashion world lately — assuming that they fit you well.  Never underestimate the power of a well-tailored pair of jeans. Pair them with some boots and a great top along with some fun jewelry.

2. Country club. When he's taking you to the family country club for the first big date, it's easy to overdo the June Cleaver look. Look at the website first or even call the club to see if they've got a dress code. Again, a conservative v-neck tee shirt or polo paired with a nice skirt and some boat shoes (Sperrys are so cute!) is the perfect outfit to wear on the green. 

3. Trendy dinner. So he's got a reservation to the hippest new place in town. The kind of place where you lean over a tiny table and share food off of even tinier plates. For a place like this, where Katie Holmes might be sitting on your right, and that new Sports Illustrated swimsuit model could be perched behind you, you're going to want to stand out.

Wear your most attention-getting top — something a little flashier than the norm. While it's not the best idea to go Vegas-crazy on a first date, this is a chance to really strut your stuff. Remember that this is part of the fun of dating — going a little outside your comfort zone! Keep reading ...

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