Best of Google Search / Tips from the stylist

The Best of Google Search: How to dress on a Date

Valentine’s Day just passed. So are we a little too late in telling you what to wear on a date? Probably not, first dates happen all the time. And no matter how many you have been to, what to wear is one of the big troubling questions. But can we be honest with you? There are no huge rules for dressing on a date. They are simple and sensible. But let’s not state them as rules. Let’s make a check list. A series of questions you can ask your date outfit.

♥ Are you comfortable and at-ease in the outfit?

On a date especially, comfort is the key. You want to be concentrating on the person and meeting them instead of maybe pulling your blouse up all the time. Or maybe you decide to wear something that fits too snug and then that distracts you all the while you are on the date. So, nothing that feels uncomfortable should be worn for the sake of it!

♥ Does the outfit reflect that you care enough to dress up?

Do you really care about going on this date? If you do then make sure that your clothes do not come across as sloppy. We are not saying you can’t wear a tee and jeans if that is who you are; you can just make sure that they are clean or put on your good shoes or accessorize well. Little things reflect that you cared enough about dating.

♥ What does this outfit say about you? Are you happy with that?

Whether we like it or not, outfits and the way we look give away our first impressions. Once we acknowledge it, we have the power to alter it. So if cleavage says sexy, big frame glasses may say nerdy. Look at your outfit and analyze what it says about you. If you are ok with being sexy, go for it. If you’d rather communicate ‘cute’ then change – it’s that simple.

♥ Where are you headed on a date? Does the outfit fit the place?

What is the venue for the date? Is it a café or a fine-dining restaurant or a movie theatre or a pub? All places require different types of outfits. So always take-in account the place and if it gets confusing, you can ask your date what they’d be wearing to a particular place, politely of course.

♥ Does the outfit flatter you? Body and skin both?

It looks good on the hanger or the magazine, but does it look good on you? That is one of the most important questions. Does the outfit flatter your body shape and the color of your skin, and your eyes etc. ? Be honest with yourself here, while you ask this question to yourself in the mirror.

P.s. Finding clothes and outfit combinations that flatter your body is extremely simple with Wink n Pout app. Give it a shot!

 ♥ How does the outfit make you feel?

Do you feel good in the outfit? Like you can take over the world? Or do you feel shy? Do you feel beautiful? Ask how you feel and if that is how you’d like to feel, you are definitely wearing the right thing even if it’s an oversized men’s shirt that traditionally no one would advise you to wear on a date!

So if, you have completed your check list, your outfit is good. But what are some outfit combinations that you can specifically wear? Should you be wearing pants or skirts or dresses? We give you options because everyone is different and there are no set rules when it comes to separates. That indeed is the only rule.

But as stylist, we give you 5 casual date outfit ideas that are vastly different in personality from each other and all of them work. So dive in!

Casual Date outfit Ideas


Dress ◊ Wedges ◊ Bag ◊ Earrings


Leggings ◊ Loafers ◊ Shirt ◊ Bag


Bag ◊ Blouse ◊ Skirt ◊ Belt ◊ Necklace ◊ Shoes


Blouse ◊ Jeans ◊ Shoes ◊ Bag


Cami ◊ Skirt ◊ Shoes ◊ Bag

And what if you are headed to a date in a nice fancy restaurant? We can still help of course. Download the Wink n Pout app and have a free personal stylist in your phone! Get outfit suggestions for all occasions in-app, shop for them or ask personal style questions as well!


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