
In this post I’m going to share my secret to creating a date night outfit that totally wows!
I’ve been around the block, and gone on my fair share of dates. I may be getting married soon but that doesn’t mean I’ll quit shopping for those dynamite looks to totally knock B off his feet!
Here is what I’ve learned:
Show some skin, but not too much! This isn’tΒ Pretty Woman, and classy is always synonymous with sexy.
You’ll notice in my outfit, I chose a shorter skirt, but a higher neckline. I focused on my long legs and even flattered them with some high heels, but I didn’t want to overly reveal by wearing a plunging neckline as well. This was the perfect middle ground.
Choose a color that makes you comfortable. Whether that’s your favorite color, or just one you know looks amazing with your skin tone.
I went with black and pops of gold. Black is always sexy in my opinion, and I feel super confident in it. Gold flatters my skin tone, so I knew the combo would be smashing!
Keep bold accessories to a minimum. If you’re wearing bright red sunnies, a printed scarf around your neck, a lip print purse, a yellow hat, and feather earrings – your date might be too distracted to focus on the true beauty: your face.
Like most gals, I love me some accessories, and I even gathered a few of my favorites together for this look. I didn’t, however, go overboard – and I stayed with my color scheme. A pair of gold earrings, a crossbody bag, some killer heels, and a fun baker boy hat were all I needed to take this look to the next level.
Outfit Details
star print skirt + blouse | heels | hat c/o Lipton Publicity | earrings c/o Spirited & Co | similar bag




Of course I can’t close out this post without mentioning my very biggest, top secret, super important tip –
Wear a smile!
It’s cheesy, but it’s true. A confident woman is an attractive woman, and if you don’t feel confident quite yet, just know that fashion is a great place to start. When you feel beautiful on the outside, that confidence within begins to show and your beauty only increases!
Don’t push away those pre-date jitters because they’ll keep you exhilarated throughout the evening. Just keep smiling, and soon, not only will your date be smiling back, but you’ll notice that you’re having more fun than you could’ve imagined!
Related Posts
A Spring Date Look Your Significant Other Will Love // What to Wear on a Valentine’s Day DateΒ // A Boyfriend-Approved Date Night Dress for Spring





Shira says
Those tips are awesome and I loveeee the layering of that gorgeous star print!
Kimberly Burke says
Your adorable! I love those pumps and the lace details on the sleeves!!! Super cute gf!!!
http://www.withlovefromkimberly.com
Stephanie Whitman says
That’s so sweet of you! I love these heels to death. There’s nothing quite like a pair of rose gold pumps to give you a confidence boost for date night π
lydia says
Okay girl, you’re seriously the cutest & so fab! Can I have this whole look, please?! Love all your tips and couldn’t agree more with you. Really love the wear a smile, part!!
Stephanie Whitman says
Well aren’t you just a gem?! Seriously, this comment made me smile so hard. Thank you!
Lacey says
Could you be any cuter? Seriously dying RN!
Stephanie Whitman says
Of course I could be cuter – I could be you! Hehe. Thanks, Lacey!
Emily Wilkinson says
Such good tips & I love that look!
Stephanie Whitman says
I love hearing that. Thanks so much for the kind words! β€οΈ
roxy says
Such a cute date night look! I agree with all of your tips, and would add that a subtle tease can be a little sexy. For example I might wear black leggings with a white-button down to work with a nude bra underneath….and then before I meet up with my fiance I might change into a black bra underneath instead for a slightly sexier look.
Stephanie Whitman says
You’re even more daring than I am. I generally don’t go for the exposed lingerie look, but I know some people who can rock it for sure!
Oh to Be a Muse says
I like your point about keeping bold accessories to a minimum. You look lovely in this hat!
Stephanie Whitman says
It’s so nice to hear you agree! I just feel like even I get distracted when I’m wearing so many accessories, so I’m sure my date is feeling that way all the more! Thanks π
KatWalkSF says
I am SO in love with your dress! You are the cutest!
Stephanie Whitman says
I love it too! The star print stole my heart immediately, and the fun layering had me hooked!
Annette Dattilo says
Confidence goes such a long way. Love the star print on your dress.
Stephanie Whitman says
Agreed 100%, and I think a lot of confidence can come from feeling great in a dynamite outfit. This look definitely gives me confidence!
Sharon Wu says
i literally love anything with stars on it so needless to say i’m in love with this dress! and anything you wear wows π hehe <3 have a wonderful week sweetie!
Stephanie Whitman says
Haha I feel the exact same way, Sharon! Star print has been my kryptonite lately. There’s just something so whimsical and fun about it! Thanks for the sweet words β€οΈ
Liz says
Such a cute outfit! And I love all of these tips! Definitely agree with being confident!
Liz
Stephanie Whitman says
Confidence is definitely a struggle for me, and that’s where I rely heavily on my outfit because when I feel like I look good, I feel much more bold and confident. Gotta love fashion – for so many reasons!
Kelsey says
Okay that dress with those heels… absolute perfection! Such a great date night look! xo
Stephanie Whitman says
Kelsey, you’re so sweet! Thanks for the encouraging words. I’m glad you like this look so much! π
Shira says
Those tips are awesome and I loveeee the layering of that gorgeous star print!
Stephanie Whitman says
Can you believe this dress came with the layered top beneath? I love the concept so much, but the great part is that they aren’t attached, so if I wanted to switch things up, I totally could – which means I can wear this dress into spring and summer no problem!
Nataly says
Great tips and even cuter dress! I love rose gold anything!
Stephanie Whitman says
Thank you so much, Nataly. I’m a sucker for rose gold as well!
Kait Elizabeth says
I love the layered look of this dress! I’m always wearing a turtleneck under stuff in the winter for warmth! Hugs, Kait
roxy says
Such a cute date night look! I agree with all of your tips, and would add that a subtle tease can be a little sexy. For example I might wear black leggings with a white-button down to work with a nude bra underneath….and then before I meet up with my fiance I might change into a black bra underneath instead for a slightly sexier look.
Stephanie Whitman says
You’re even more daring than I am. I generally don’t go for the exposed lingerie look, but I know some people who can rock it for sure!
the eye traveler says
such a lovely outfit for a date night. beautiful yet also keeps you warm, what an ultimate goal?!
http://www.theeyetraveler.com
Stephanie Whitman says
Definitely! I appreciate the fact that Chicwish kept winter in mind when they came out with their latest line of cute dresses. I don’t have to worry as much about freezing to death but I still feel super cute!
Kelsey says
Okay that dress with those heels… absolute perfection! Such a great date night look! xo
Stephanie Whitman says
Kelsey, you’re so sweet! Thanks for the encouraging words. I’m glad you like this look so much! π
Kait Elizabeth says
I love the layered look of this dress! I’m always wearing a turtleneck under stuff in the winter for warmth! Hugs, Kait
Stephanie Whitman says
I love that too. That’s why I was so excited when this dress came already layered. Such a unique piece!
Rachael Thomas says
I’m in love with this star print dress on you, and these are such great tips! The gold accessories and hat look perfect!
Rachael
Stephanie Whitman says
Thanks a million! I am a huge star print junkie haha so this dress was made for me!
Kileen says
Great tips babe and your outfit is so cute!! I am loving that star print!
Kileen
cute & little
Nicole says
Yes ππ» definitely smile, what a difference it can make!! Love your tips, and you are just the cutest, love your posts so much!!
Stephanie Whitman says
Goodness, it makes a difference even just to me when I smile! So important. Best accessory there is!
Kileen says
Great tips babe and your outfit is so cute!! I am loving that star print!
Kileen
cute & little
Stephanie Whitman says
Thanks so much cutie! Star print has become a serious obsession of mine. I think I’ll be putting together a full star-print round up soon!
Helen says
This are great tips! And I love your outfit, you look so fab! I also love your gold rose shoes. Perfect for your black dress! π
Stephanie Whitman says
I feel like I can run the world in these rose gold heels. They are seriously stunning!
Julia Comil says
Love your shoes and dress!!! So pretty!!! The hat is the perfect final touch
Stephanie Whitman says
Aww thank you, Julia. You have no idea how nice that is to hear because I was totally worried that I couldn’t pull off this hat haha!
Cara Newhart says
You’re too cute! I love how unique this outfit is and those gold heels are ah-mazing!
xo, Cara
https://brighterbold.com
Laura || Walking in Memphis in High Heels says
Amazing tips! And I love love love your dress! It’s so cute and flirty, and I love the heels! Great outfit!
Stephanie Whitman says
You’d seriously look adorable in this dress! It’s such a fun one with the layered mock-neck top beneath!
Rach says
You nailed it with your outfit tips! And this dress of yours is so cute! It is a good mixture of flirty and classy!
http://www.rdsobsessions.com
Stephanie Whitman says
That’s the best thing to hear. Thanks a million, gorgeous!
Cara Newhart says
You’re too cute! I love how unique this outfit is and those gold heels are ah-mazing!
xo, Cara
https://brighterbold.com
Stephanie Whitman says
I agree with you 100%. These rose gold heels are one of my favorite pairs of shoes because they’re just such fun!
Laura Leigh says
You look SO fabulous and I LOVE how much fun you’re having in these photos!!!
xo Laura Leigh
http://www.louellareese.com
Stephanie Whitman says
That’s so sweet of you to say! I definitely love having fun with my photos. I want people to see my personality more than anything π
prachi says
love the lace details and the pumps
Laura says
Love your date night outfit!! These are all great tips. I love getting dressed up for date night with my hubby too!
xo, Laura
Stephanie Whitman says
There’s something so special about walking into the room in a gorgeous dress and my fiancΓ© just going, “WOW!” And I’m sure you understand that!
Laura Botkin says
This outfit is so cute!! Love the tip about smiling! I have always struggled with it when I was dating!
Stephanie Whitman says
Oh my goodness same here! I would just be so insecure and stressed out on dates haha. Thankfully my fiancΓ© is great at making me smile so I don’t have to try so hard anymore π
Jessica says
You look so cute here! Love that dress! So important to smile all the time!
xo Jessica
http://www.whatsfordinneresq.com
Stephanie Whitman says
I can’t even rave enough about this dress. It’s seriously the cutest of all time! I feel 100x more confident when I wear it!
prachi says
love the lace details and the pumps
Stephanie Whitman says
Thanks so much!
Ruth Ridley says
And you wear the best style!!! You are killing it in this dress mama!!
Stephanie Whitman says
Awww that’s seriously the nicest thing to hear! Thank you, gorgeous!
Denise Kokinis says
Totally agreed on showing a little bit of skin but not too much! I love the bit of subtly that goes into wearing an outfit for date night! I love the way you put this together, it is sooo cute!
Denise | Fashion Love Letters
Anna English says
I totally agree, CLASSY IS ALWAYS SYNONYMOUS WITH SEXY! Cute star print too!
Stephanie Whitman says
Yes! I love that you agree! I don’t feel like I have to show all my goods to the world to feel sexy. Sometimes covering up can be even more alluring! Classy is definitely sexy β€οΈ
Kylie says
Gorgeous girl you are ROCKING this look! LOVE your cute tips too!
Stephanie Whitman says
Oh my gosh that’s the nicest thing to hear. Thank you so much!!!
Sara says
Those heels are so fun and I love your quilted bag! And I agree that the key to date night sexy is to highlight your best/favorite feature and leave the rest to the imagination!
xo, Sara
Stephanie Whitman says
You can’t go wrong with rose gold heels in my opinion π And I’m so glad you agree! I think that’s a super important thing to remember for date nights!
Whit says
LOVE how you layered this dress over a cozy turtleneck! Your style game is strong!!
love,
Britt+Whit
Stephanie Whitman says
It actually came that way π The pieces can come apart, but I love them together for winter!
Denise Kokinis says
Totally agreed on showing a little bit of skin but not too much! I love the bit of subtly that goes into wearing an outfit for date night! I love the way you put this together, it is sooo cute!
Denise | Fashion Love Letters
Stephanie Whitman says
I think subtly is super important when it comes to date night outfits. Leave some of it to the imagination hehe
Steph says
I am so in love with this whole look! You are killing it.
xo,
Steph
@trendyinindy || trendyinindy.com
Stephanie Whitman says
Thanks so much, Steph! I’m so glad you like it!
LuxMommy says
Yes, the perfect date night look. I love this and that purse is too cute!
Stephanie Whitman says
I agree 100%. This look is great for date night or really any other occasion as well!
Ashley says
This dress is SO darling! I love the star print and love how you styled it!!
Stephanie Whitman says
Thanks so much! Star print is such an obsession of mine lately!
Azanique Rawl says
This dress is so cute! What a fun outfit π
-xo, Azanique | http://www.lotsofsass.com
Azanique Rawl says
This dress is so cute! What a fun outfit π
-xo, Azanique | http://www.lotsofsass.com
Stephanie Whitman says
Thanks you, gorgeous! I sure do love a good statement dress!
Jenn Hanft says
Ahhhhh I’m so in love with your style and your smile! I love the stars on this little black dress that make it so much more cute! Layered on top of a turtleneck is perfect for the colder weather. And girrrrrl you know how to pull off hats π I wish I can pull off hats like that haha. Bookmarking this for date night tips hehe muahh <3
With love, Jenn
https://jubilantdose.com
Carolyna Bauer says
love this look! I love dressing up classy! XOXO,
Carolyna
@carolynabauer // carolynabauer.com
Jenn Hanft says
Ahhhhh I’m so in love with your style and your smile! I love the stars on this little black dress that make it so much more cute! Layered on top of a turtleneck is perfect for the colder weather. And girrrrrl you know how to pull off hats π I wish I can pull off hats like that haha. Bookmarking this for date night tips hehe muahh <3
With love, Jenn
https://jubilantdose.com
Carolyna Bauer says
love this look! I love dressing up classy! XOXO,
Carolyna
@carolynabauer // carolynabauer.com
kelly Fordon says
Such a darling date night look! I’m all about star lately, so naturally, I NEED that dress!
Birdie Shoots
Julia Comil says
Love your shoes and dress!!! So pretty!!! The hat is the perfect final touch
Helen says
This are great tips! And I love your outfit, you look so fab! I also love your gold rose shoes. Perfect for your black dress! π
Nicole says
Yes 🙌🏻 definitely smile, what a difference it can make!! Love your tips, and you are just the cutest, love your posts so much!!
Stephanie Whitman says
Goodness, it makes a difference even just to me when I smile! So important. Best accessory there is!
LuxMommy says
Yes, the perfect date night look. I love this and that purse is too cute!
kelly Fordon says
Such a darling date night look! I’m all about star lately, so naturally, I NEED that dress!
Birdie Shoots
Ashley says
This dress is SO darling! I love the star print and love how you styled it!!