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What to Wear on a Date

what to wear on a dateRuthlessly rummaging through her closet, Kate pulled piece after piece out, grumbled, and threw it on the bed.

  • Sequin miniskirt?  No, that work.
  • Tuxedo stripe track pants and blazer?  No, that’s wasn’t right.
  • Pleated skirt?  No, that wasn’t right.
  • Designer crop top?  No, that wasn’t right.

In a huff of irritation, flopped on the bed and looked at the jumble of clothes and still was clueless as to what she was going to do about Friday.  Indecision swam in her head as her mind screamed “What do I wear on a date?!”

Has this ever happened to you?

Well if it hasn’t consider yourself blessed and fortunate.  If you’re like me, then this scene has definitely happened to you a time or two (or seven!) when you just had no clue what to wear on a date.  This situation becomes even more overwhelming when you are trying to figure out what to wear on a first date!

Here are my timeless tips on what to wear on a first, second, or twelfth date!

For the casual date

Remember that comfort, versatility, and clean lines should be your goal.  Choose pieces that can be easily layered in case you’ll be going some place where the climate may change (i.e. the movies, walk in the park, etc.) and you want to be comfortable the entire time.  Also keep in mind to wear shoes that are cute as well as comfortable.  Leave your 5” stilettos in the closet for this type of date (this is about the only time you’ll hear me advise against wearing your sky high heels:)  A beautiful flat sandal, loafer, lace up oxford, or ballet flat may be your best choices.

For the formal date

Bring on the glam!  This is the type of date you can get all dolled up for because you’ll likely be sitting in one place and there will be less movement as compared to a casual date.  Think a beautiful dinner date.  The goal of this look should be functional femininity.  While a fabulous bandage dress, smokey eye, and deep red lips might be perfect for the woman with a boat load of confidence and the perfect body, for most women this can be a bit overkill.

Go for pieces with silhouettes that compliment your shape and are preferably made of wrinkle-resistant fabric. You’ll likely be sitting for a long period of time, so anything that can reduce the amount of creases in your clothes when you get up is a plus!  Also think classy instead of overtly sexy.  Yes men like cleavage but if you want your date to look in your eyes when they talk to you (and not your breasts) try to go for drape style tops and dresses that accentuate not necessarily show off “the girls”

Separates can look fabulous here!  Think of a great a-line or fishtail skirt.  Work with the silhouettes that look good on  you.  Here’s where you can go back to your high heels (yes!), just make sure you can walk comfortably in them.

So there you have it, my fast easy and effective tips on what to wear on a date.

Tell me, what do you wear on casual dates?

What do you wear on formal dates?

What do you wear on a first date?

Comment below!

Still need a bit of guidance?  Then check out my ultimate series of what to wear on dates:


Dress to Impress: How to Wear a Maxi Skirt

how to wear a maxi skirtThe maxi skirt…

This is one of the true transitional pieces that should be a staple in every woman’s closet.  By definition the maxi skirt is an ankle length skirt.  However there are so many ways this ankle length skirt can be worn.  If you go for one in heavier jersey knit or a lightweight crepe it will be the most versatile in your wardrobe.  If you ever wondered how to wear a maxi skirt, here are a few ways that will take you from day-to-night, casual-to-formal and back again!

Stylist Fashion Tip#1: Maxi Skirt + Denim Jacket

This is a look that works best with a richly printed maxi skirt.  Pair the skirt with a cropped or hip length denim jacket that has a great cut to accentuate the waist.  No boxy jackets here!  A beautiful semi-sheer tank and flats will make this a perfect look for a casual date, a day at the museum, or running errands around the city.

Stylist Fashion Tip #2: Maxi Skirt + Crop Top

I like this for more of a dressy or evening look.  Pair a maxi skirt with a crop top that looks good on your body. The material of the skit should say “chic and sophisticated”  Go darker on the bottom and save the beautiful print for the crop top, because after all that’s the show piece of this look!  Throw on some strappy heels and grab an evening clutch and you’re ready to go.

Stylist Fashion Tip #3: Maxi Skirt + Collared Blouse

If you want to take your love for maxi skirts to the office, then try this combo:  pair a maxi skirt with an embellished collared blouse for an easy business casual look.  To ensure your look stays work appropriate, avoid maxi skirts made of jersey knit or modal as these materials are too clingy to be flattering in an office environment.  A maxi skirt with more structure (and preferably a lining) will work best for an office look.

Some great fabrics to pick for a maxi skirt you plan to wear to the office include:

  • chiffon
  • crepe
  • lace overlay
  • silk
  • silk-crepe.


Stylist Fashion Tip #4: Maxi Skirt + Tee

For fun and functional a maxi skirt paired with a v-neck tee is very flattering.  What you’ll be doing that day will determine the best shoes to wear with this look.  If you’ll be running errands, a pair of canvas sneakers will be a good choice; if you’ll be doing lunch with friends, try a breezy scarf and peep toe patent leather wedges for a flattering look with a hint of vintage.

Stylist Fashion Tip #5: Maxi Skirt worn as Maxi Dress

Lastly you can make your maxi skirt the whole outfit!  For this look, simply wear your maxi skirt as a dress by pulling it up under your armpits.  For this look to work, you want a maxi skirt with an elastic waistband that’s not too structured.  Good foundation garments (read: underwear) are also important.  A strapless bra or strapless shaper will provide a bit more “grip” to help the maxi skirt stay in place.  Give this look plenty of shape by wearing a wide belt and a cropped cardigan.  My suggestion is to go for a skirt that has rich colors and patterns and choose accessories in solid darker complimentary colors.

Now you know how to wear a maxi skirt in a few amazing ways, which ones will you choose?

Tell me below!


Shop My Picks for Haute Maxi Skirts!



Dating on the Rebound

Dating on the Rebound
Rebound dating

It’s a crazy, loony, and possibly funny place most of us have been.

After a relationships ends, it’s quite common to go “on the rebound” and kind of date people who aren’t in your usual scope.  This can be a good or bad thing, all depending upon where you’re head is at when you do it.

In our latest book with fab dating advice for women, we discuss several ways on how to secure the relationship you want using some methods you may have never been taught or simply forgotten about.   However our “sage advice” doesn’t usually apply to women on the rebound.

Here are some helpful articles about dating on the rebound…whatever your stance is on the subject:

Want more?  Here’s also a great list of resources that dive a little more in-depth on the subject:

So have you ever been on the rebound?

Was it a good experience or a terrible time in dating?

Comment below!


photo credit: las – initially via photopin cc

Weekly Roundup-Vol.5

weekly roundup - vol.5

Here are my favorite posts from around the fashion world this week!

I. Fashion


II. Personal Style


III. Street Style


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