Inspiring Conversations

Penny’s Fashion Firsts

  • SumoMe

The first time always seem the scariest with all that anxiety building up in your tummy and butterflies that flutter so uncontrollably you’d wish your innards could catch them. But the fact is, first times are the most exciting periods in life you’ll ever experience. Treasure them because they only happen once!

By Serene Tham & Penny C

Our contributor, Serene reckons fashion to the 3R’s-
Recycle: Reviving nostalgia.
Reduce: Where less is more; Where dollar does not equates to style.
Reuse: Fashion has no constraints, you can’t classify it, you don’t define it. It is a form of self-revelation.

Especially when it comes to fashion, styling yourself up for first impressions is quintessential and we’re sharing with you looks to go with your first trips to wherever you feet takes you! We do this so you won’t feel the apprehension, only the thrill of where life’s going to take you for the first time.

1. The Transient Face (First Aeroplane Flight)

The transient face

The transient face by Penny’s Daybook featuring a tall vest

A luggage of: long sleeve, high-waisted slacks, vest

Removable pieces are a must for a traveller! Pieces that bring you from day to night, summer to autumn, which allows you to glam it up or take it off, according to your whims and fancies.

2. Hello Sunshine! (First Picnic Outing)

Hello sunshine

Hello sunshine by Penny’s Daybook featuring topshop shorts

A basket of: printed bralet/corset, pleat shorts, knotted crop top

Bright skies with the right amount of fluffy white clouds to give the day a cool start. It’s a great moment to get out there and let the wind ruffle your thoughts and your cherry pink sleeves! Once you’re dolled up in fun tones, accessorise with best friends and a beautiful, well packed picnic basket. You know how it goes, keep your friends clothes, but keep your strawberries closer. Don’t forget that lomo camera!

3. Museum Mannequin (First Trip To A Museum/Art Gallery)

Museum Mannequin

Museum Mannequin by Penny’s Daybook featuring a pink skirt

An exhibition of: crochet crops, leggings/ knee-high socks, ballet flats, skirts

So we say, Art is fashion; fashion is art- anything goes. Monumental moments are best paired with varied lengths of socks, patterned or sheer leggings with your all time favourite ballet flats. Think romantic in hues of baby pink, dreamy white and concrete greys.

4. Urbane Candidate (First Job Interview

Dress the part with: structured dress, heels, statement bag

There’s something in the air… Something a little frisky, a little scary. It smells of opportunity, it smells of cash. The palms are sweaty, the brain’s a train wreck. Adrenaline rush, natural blusher, hearts on fire. Until a voice calls out for your name. A chance you’ve been waiting for to impress, and it starts with the right outfit and a mega-watt smile.

5. The Trail Seeker (First Time On A Hiking Trail)

The trail seeker

The trail seeker by Penny’s Daybook featuring a corduroy hat

Going the tree top walk with: playsuit, lace-up hiking shoes, knee-high socks

Dress light, grab your essentials and head out to catch the sun rays in the tree tops. Let the wind colour your skin a golden hue! Hang on tight to the ropes, the simplicity of seeking the trail in style will blow you away.

6. Midnight Lush (First Party)

A tease of: seductive shoes, fitted dress and spunky accessories

Walk into a room of mesmerising lights and music an alluring mystery and leave the party a queen.  There may be hundreds in the room but you’re turning heads with your enigmatic glance, teasing eye shadow and a courting dress to match. The boys are looking your way and the girls are whispering to each other. You could just be royalty.

7. Sexy Boots (First Rock Concert)

Sexy Boots

Sexy Boots by Penny’s Daybook featuring ankle booties

Rock it with: casual rips, solid shoes, and out with the layers.

Get dressed and get high on music that’s going to drown your worries! Pick sensible concert clothes and shoes that are light, weather/mud resistant and impeccably cool and comfortably you. Nothing too shabby, of course. Hands are in the air ‘cos it’s time to get your boots on!’

So what do you think of the looks? The itch to upgrade our wardrobe is getting stronger, even for us. And now the things are getting more exciting! 1 lucky winner will walk away with a charming Tears and Rain Draped Dress from online boutique, Lacepipe!

Here’s how to win – out of the 7 looks we’ve created, tell us which is your favourite and why!

As usual, we’re making it simpler and more accessible for our tech savvy readers out there…there’re 2 ways to grab this lovely gift!

1. You can either EMAIL us
Send your preferred look to and don’t forget the following details:

  • Name
  • Age
  • NRIC
  • D.O.B
  • Contact number
  • Occupation

2. Or TWEET us!

Tweet us at @PennysDaybook with your selected look and if you’re our winner, we’ll give you a direct message.
Please be reminded that this contest is only open to readers living in Singapore.

All entries must reach us by Monday, 29 November 2010! We can’t wait to hear your choices!You’ll be hearing for us soon

Congrats to Faith Tan on winning the dress! :) Urbane Candidate (First Job Interview) is her favourite look and for the curious, take a peek at what the our Urbane Candidate is made of!

It’s not how good you are, it’s how good you want to be

Almarc Heels
$245 –
High heel pumps »

$9.98 –
Oversized rings »

Suede Metal Heart Belt
$40 –
Suede belts »

Style city Style city book
35 GBP –

It’s not how good you are, it’s how good you want to be by Penny’s Daybook featuring aldo jewelry

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