3 First Date Outfit Ideas from hush – Judged by a Man I Used to Date!

Ella Gregory Cocos Tea Party Hush

As many of you know, I’m currently single and navigating the complex world of online dating (offline dating doesn’t appear to exist any more). I’ve now mastered the art of first date chat, but still struggle when it comes to first date dressing.

There’s so much pressure, because you naturally want to look your best. But, make too much of an effort and you run the risk of coming across a bit try-hard. I therefore think it’s best to stay true to your personal style when getting ready for a date, and choose something that makes you feel comfortable and confident.

My wardrobe is filled with pieces from hush, and I regularly wear their designs on first dates. After hearing this, the hush team challenged me to put together three first date outfit ideas from their insanely-covetable autumn collection. This sounded easy enough. But, really, I’m no expert. How do I know what makes an appealing first date look? So I decided to do some proper research, and invited a man I used to date to judge all three outfits…

Christian and I dated briefly last year whilst he was living in London (he’s a native New Yorker), and have remained friends. He very generously offered himself up to be used as clickbait for this post, and provides his unbridled fashion opinions below.

Look #1: The Romantic Midi Skirt

First Date Outfit Ideas Fall 2017

Hush Leopard Print Handbag
Love Knit Hush

I’M WEARING: Love knit sweater, lace midi skirt, leopard print handbag and block heels. All by hush.

I’m not sure if there are rules against wearing clothing emblazoned with the word ‘Love’ when you’re going on a first date, but I couldn’t resist this adorable knit! Paired with the lace midi skirt skirt it creates a soft, romantic look without appearing overly-feminine.

If you have a date lined up that feels dauntingly formal (dinner, drinks at a swanky bar or theatre tickets), this outfit is a real winner! The lace skirt and heels keep things on the dressy side, but the knit adds a dose of casual cool and will help you remain comfortable if feeling overdressed is a big concern. (FYI: This textured camisole would also look great with the midi skirt).

Christian’s Verdict: “This is cute. But I personally think slogans or ironic messages are a bit of an eye roll on a date. However, as long as your clothes make you feel comfortable and allow your personality to shine through it’s all good.”

Look #2: The Flirty Little Black Dress

First Date Outfit Ideas Little Black Dress

Date Night Outfit Ideas LBD
Leopard Print Ankle Boots Hush

I’M WEARING: Bell sleeve dress, leopard boots and cross-body bag. All by hush.

I felt the most “date ready” in this outfit. Probably because a little black dress is always a safe bet. And this bell-sleeved number was definitely made for date nights! The flirty sleeves and short hemline provide some sex appeal, but the comfortable, loose fit prevents it from looking too flashy. I added leopard print boots for a pop of colour, and was ready to go…

Christian’s Verdict: “This is easily the cutest – just a little neckline, just a little leg… It seems to be the classic little black dress. I like that it has an element of casual, but it’s still dressed up. It looks cool.”

Look #3: The Man Repelling Mules

First Date Outfit Ideas Hush

Mustard Mules Hush
First Date Dressing

I’M WEARING: Leopard blouse (available from September 26th), leather leggings, mustard mules (also available in black), and cross-body bag. All by hush. 

“Fancy grabbing a drink after work this week?” is now the go-to line for men asking women out on a date. It doesn’t show a great deal of effort, let’s be honest. So the aim is to appear equally as casual when dressing for such a liaison. And that’s why leather leggings and statement tops are a match made in heaven. It’s a cool, stylish combination that doesn’t appear too try-hard!

I may have gotten a little overconfident when it came to my choice of footwear, however. These mustard slip-ons are super-cool, but do straight men understand the appeal of mules?! Perhaps they’re best reserved for dates with the girls…

Christian’s Verdict: “I don’t think this outfit is man-repelling. But my first thought would definitely be, ‘Oh, okay. She’s really into shoes.’ If I complimented the shoes I’d be lying, but it would mean I liked whoever was wearing them.”

The Verdict

Although outfit #1 is actually my favourite from the bunch, I felt the most confident and “date ready” in the bell-sleeved little black dress. And, unsurprisingly, Christian also agreed that that was the best date night outfit. So, next time you’re panicking what to wear on a date, head straight to hush, order a LBD and style with a pair of sassy ankle boots!

What are your go-to first date outfit ideas? And which of these hush looks is your favourite? Leave a comment below to have your say…

~ This post was sponsored hush. Thank you for continuing to support the sponsors that make Coco’s Tea Party possible. ~

Photos by Victoria Metaxas


  1. Maz says:

    Ok, this is genius. I also LOVE the second outfit! Christian has great taste 😉

  2. Sol says:

    Well..this made my Monday morning! Re: slogan knit, great sweater but I got commitment-issues shivers just from looking at it so I see the risk of that outfit haha x

  3. thelikelylady says:

    This was such a fun post – I’m no longer single but if I was I’d be snapping up outfit number 2! Those booooots!

    Laura x

    • cocos_tea_party says:

      So pleased you enjoyed the post, Laura. And the boots are dreamy, aren’t they? So comfortable too, I must add! xx

  4. monicawelburn says:

    Ah love this post sweetie! It’s SO fun and you look gorgeous and date-ready in every single outfit! #1 is my favourite too!


  5. Flic says:

    Outfit #2 is 100% my pick, love it! Such a good post xx

  6. Loved this Ella, fab idea! And as for the looks, I can’t pick, love them all for different reasons!

    Mel x mediamarmalade.com

  7. I love this idea for a post – I also think that outfit number 2 would have been the one I picked! Super cute!


  8. Julia Bryson says:

    Love this post and as someone who is dating and loves Hush found it really helpful! My current date night fave is a blue and black floral Hush dress. I personally love the LBD and leopard xx

  9. Noemi says:

    I would choose outfit number 2, too! It’s feminine but not “try hard” and I love black dresses and leopard shoes. That outfit would be perfect for many different occasions.
    And I admire who can walk with those mules because they would slip off my feet every two seconds!

    • cocos_tea_party says:

      Haha! Yep, miles are so hard to walk in. And you’re right, outfit number 2 would be perfect for some many occasions!

  10. Pingback: Why I'm Breaking Up With Dating Apps - Coco's Tea Party


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