What To Wear On A Date


Ever wondered how to pick the perfect OOTD, or what to wear to a wedding? Blogger Jessica Tham answers all of your Fashion FAQs in this column about all things fashion!

What To Wear On A Date

No idea what to wear on your next big date? Fashion blogger Jessica Tham (@tippytapp) shows us how to put together some easy looks for different occasions.

1. Outdoor Date: Romantic Retro

As idyllic as it may seem, going on a picnic date or romantic garden stroll in our humid weather is somewhat daunting. But hey, that’s what Gardens by the Bay is for right? Just kidding.

But really, an outdoor date doesn’t mean you have to schlep around in shorts and slippers – unless you’re planning to head to the beach, that is. While it may be tempting to fall back on your usual tank top-and-shorts combo, there are many other sartorial options that will keep you cute and comfortable.

For something a little more OOTD-worthy, try a retro-inspired dress in a lighter fabric like linen. Not only is it comfortable enough to wear on a hot day, but the midi hemline will also protect your modesty from the elements. (A short skirt on a windy day? No thanks.)

To complete the look, add a mini bag, your favourite pair of flats and a bright lippie for a pop of colour. Ahh, the perfect outfit to take a walk down memory lane with your date…then get him to take your OOTD photos, of course.

2. Classic Date: Comfortably Cute

If you prefer to stick to something safer, a classic midi dress is a fun option for a dinner and movie date. An A-line cut will work with most body types (and hide any potential food babies *ahem*), while a pretty hue will keep the look casual but cute.

To keep the outfit from looking sickly sweet, pair your midi dress with a pair of oxfords for a bit of edge. Complete the look with a structured bag and ta-daaaah – easiest, breeziest date outfit ever.

3. Dinner Date: Fun and Fabulous

Dinner dates are the perfect excuse to dress up, so why not bust out that party dress you’ve been dying to wear (but has just been sitting in your closet)?

Lace details have been all the rage this season, but the trend can look a bit busy (or worse, bridal) with certain styles. To keep the look polished, stick with a fitted cut that will accentuate your body. A trumpet-style hemline is also a fun alternative to the traditional A-line or pencil cut.

Complete your outfit with a pair of killer pumps and you’re all set to dazzle your dinner date. Now, go forth and be fabulous. #yougotthis

Got any fashion-related questions for Jessica? Email us or leave a comment below. For more of Jessica, follow her on Instagram or check out her blog. Check out other fashion articles from her Fashion FAQs column here.

Still want more? Check out these other articles:

Festive Outfit Ideas

How To Style A Midi Dress For Different Occasions

Tippytapp’s Favourite Taobao Stores

Lipstick Hacks To Get The Perfect Pout