Monday, July 5, 2021


By Guest Contributor

Photo created by freepic.diller -

As Tom Ford expertly says, “dressing well is a form of good manners.”

And when you’re meeting for a first date, it’s not just good manners that you want to show, it's also a good impression that you want to make.

Now now, don’t freak out because you don’t know what to wear on a first date.

Here are 10 first date outfit ideas you can try out — guarantee to turn heads and keep your date’s eyes on you.

1. A Dressy Blouse + Relaxed Jeans + Midi Heels

Photo created by lookstudio - (Click to enlarge)

If you love wearing jeans but want to dress them up a bit, try a wrap top or anything made of a more formal fabric like silk or velvet.

Finish the first date look with low-heeled shoes to create a balance between comfort and elegance.

2. Going-Out Top + High-Waisted Denim + Low Heels

Photo created by kroshka__nastya -

A date outfit formula that you can reuse — the focus is the going-out top.

Choose a going-out top that energises you and makes you want to have a good time, whether it's flowing or form-fitting, off the shoulder or strapless, sequined or ruffly.

3. A Printed Skirt + T-Shirt + Flats

Photo created by haritanita -

This first date outfit is ideal for anyone who likes wearing skirts but also enjoys wearing casual and comfy clothes.

It’s also a good outfit idea that can work in the day or night time. Make sure you choose a fun print so that the outfit doesn’t look too bland.

4. Knitted top + plaid skirt

Photo created by kroshka__nastya -

For a fun and flirty first date outfit, pair a knitted top or cardigan with a plaid mini skirt to get that Korean girl vibe.

You can also choose to wear them in pastel colours which is totally the trend nowadays. This first date outfit idea is easy to put together and you will look so sweet, your date might just melt.

5. Flowy Midi Dress + Sneakers

Photo created by lookstudio -

A lightweight midi dress is the ideal thing to wear when you're out for ideas on what to wear for a first date.

Wear it with sneakers if you think you’re going to be walking a lot or put on a pair of strappy sandals if you want to go for that sweet first date look.

6. Silk Cami + Jean Shorts or Skirt + Slides

Draped Silk Cami (Photo courtesy of Vince)

When it’s too hot of a weather but you still want to look effortlessly good, a silk cami with denim shorts or skirt is a great first date outfit idea.

A silk cami will provide a sleeker, more sophisticated look, and a pair of low-heeled mules will help dress things up.

7. A Bold Blouse + Skirt + Sneakers

Abella Tulle Puff-Sleeve Blouse (Photo courtesy of Alice + Olivia)

Who says you can’t dress bold for a first date outfit? Whether it’s oversized sleeves or bright colours, you can wear whatever you want as long as you look good in it.

Honestly, the sneakers are just for comfort. You can always go for heels especially if it’s for a night out.

8. Floral dress + Accessories

Printed silk-trimmed satin midi dress (Photo courtesy of R13)

Another easy outfit to put together, a floral dress is a guarantee win for a first date outfit. It’s romantic, it’s sweet and you can dress it up or down however you like.

Ideal for a coffee or a brunch date, add a pair of shades and put on your sneakers and you are first-date ready. Go for a maxi dress with a sexy side split if it’s for night out.

Most importantly, remember to accessorize — cute bag, floppy hat, chunky earrings, layered rings, etc. — there are tons of ways to elevate your look.

9. Slinky Slip Dress

Satin Slip Dress (Photo courtesy of Vince)

A satin slip dress is the perfect first date outfit if you’re meeting up in the evening. It’s nearly lingerie, so it doesn’t get any sexier than that. But if you want to go for a more relaxed vibe, you can always wear it over a fitted tee. Pair it with some chunky earrings and elegant sandals to complete the look.

10. Classic LBD + Boots

If all else fails, you can always fall back on the classic little black dress and a pair of low-heeled boots. Turn the first date outfit into a casual day look by layering a denim jacket over or if it’s a night out, play up your makeup and put on some fancy jewelry to go with the look.

Now that you’ve got your first date outfit down, here are some tips and ideas for a successful first date in Singapore.💖

What? You don’t have a first date to go to?

Oh, no worries! We also got that you covered, besties! 

Hop on over to Singapore’s sugar daddy app - Sugarbook and start searching! Who knows, your first date might lead to a sweeter connection and even receive some new threads to upgrade your closet. 😉

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