Whether you go out for Happy Hour with co-workers, start the weekend off with gal pals, or maybe it’s a first date option, but it’s not too early to start thinking about what you’ll wear.  Your choice of what to wear may be different, depending on who you are meeting up with,but thing ahead will ensure you’re looking great.

Co-worker Happy Hour with co-worker means you’ll be coming from work, so an all-out wardrobe change is not going to be an option.  Just plan what you’ll After work Happy Hour wearing that day ahead of time, so you can make a quick adjustment for a new look.  Ideas:

  • Wear a camisole beneath a jacket (even the most conservative suit attire), and then slip the jacket off for Happy Hour.  No one will notice that you’ve “changed” your outfit, they’ll just notice that you look cool and casual.
  • Add or subtract a scarf.  Take off a scarf and tie it to our bag, or the reverse, and a simple accessory changes your look for work-like classic to Happy Hour chic.
  • Wear bolder jewelry.  It may not be every day work fare, but it can change the look of otherwise conservative business attire.
  • If your work in a casual environment, wear a simple sun dress.  Top it with a jacket or sweater for that air conditioned office, but shuck it off for Happy Hour.
  • Wear your business suit.  Business can be sexy, and hundreds of fantasies have been spun out around that theme.

Gal pal Happy Hour can be a prelude to an evening out, of just time to touch base before heading separate ways for the weekend.  Which it is may dictate how you dress.  Ideas:

  • If you have time to change, a simple little black dress will always work.
  • If you’re coming from work, bring a sexy and fun dress to change into.  Try something new, if you’d like, your gal pals will give you honest feed back.
  • Jeans.  Always appropriate for the gals.
  • With no time to change, tuck a pair of sexy heels in your bag, and shuck off the blazer.
  • Casual Friday may give you options that you wouldn’t otherwise have, and if so, take advantage of it by wearing jeans or capris.  Dress up with a collared shirt, or down with a flouncy top.  Change into spiky heels for Happy Hour

First date Happy Hour is a tough one.  It can be a simple way to meet someone in a low-stress, no commitment environment.  You want to look terrific, but without looking like you tried too hard.  Ideas:

  • Business attire.  If you’re coming from work, you can what you wore to work (see above).  I’d pass on wearing a suit, though, unless you’re both lawyers coming from court or accountants coming from and IRS meeting.
  • A little black dress, but keep it even simpler than you did for with the gals.  You want to look chic and put together, but you don’t want to look overdressed, or like you’re headed off to the prom.
  • A sexy black skirt or well tailored pair of black pants, whichever you feel more comfortable in.  Pair it with an equally sleek top for the Audrey Hepburn look.
  • Solid color sundress.  Save the flowers and fussy patterns for the gals, but a solid color sun dress with some sexy sandals scores high with the guys.
  • Skinny jeans and heels.  Choose a looser, flouncy top to offset the skinniness of the jeans  This should become a classic first-date outfit.

Do you have a go-to Happy Hour outfit?  What is it, and why does it always work for you?

Photo credit: It’s Holly @flickr