All Dressed Up: What To Wear On A First Date

polyvore board 1. Topshop floral dress /2. Butter London nail polish/ 3. MARC BY MARC JACOBS leather bag/4. Topshop black shoes/5.  Alice Olivia jacket/6. Rag Bone pocket tee / 7. Mango slim jeans/ 8. Dorothy Perkins white handbag /9. Pink Pumps/ 10. H M black top/ 11. Topshop pleated skirt/ 12. Forever 21 purse /13. Zara leather sandals /14. H&M aviator glasses


Choosing what to wear for a special occasion is always a little daunting but when it’s for a first date then it can become down right stressful. On the one hand, you want to feel pretty and confident but on the other hand, you also want your outfit to reflect your personality, to make the right impression on your date and to look sexy but not too sexy. All of this whilst not looking like you’re trying too hard of course! Sounds like a tall order, doesn’t it?

To ease the pressure off your next big date I’ve assembled some tips to help you pick out the perfect outfit. And even if your date doesn’t turn out to be the man of your dreams at least you’ll still feel fabulous!

Don’t go over the top. Just because it’s a first date don’t feel that you need to buy an expensive new dress or run to get your makeup done at M.A.C (unless you can totally afford it in which case good for you (and I’m very jealous)). At the end of the day your date is really interested in you not your outfit so there’s no need to empty your bank account for the occasion (save that for when you two get married). Also remember to be yourself; for example, don’t suddenly start dressing up head to toe in sequins if you’re more of a girl-next-door at heart. After all, there’s nothing less attractive that someone who’s pretending to be someone else.

Dress for the occasion. Make sure you know where you are heading to for your date ahead of time so that you can dress appropriately. I’ve put a few options together (see above) in case you get stuck or don’t really know where to start. Hopefully you should have similar items in your wardrobe already and just need to mix and match them. When in doubt, always go with your favorite little black dress. It’s a classic choice for a reason!

♥ Don’t wear anything you’re not comfortable in. Yes, those high heels are fabulous but falling flat on your face in front of your date is not. Unless you’re confident walking in high heels I’d suggest you wear some low to medium high heels or wedges instead. Also, avoid anything that you can’t sit in comfortably. No date is worth you not being able to breathe!

No need to go to the other extreme either. Obviously items such as crocs, baggy track pants, worn/dirty clothes should be left at home (or burnt, whatever).

♥ Leave a little to the imagination. Unless you’re dating someone from the cast of ‘Geordie Shore’ you probably don’t want to show too much skin on the first date. I’m not saying you should dress like a nun but maybe choose between showing off your legs or your bust for example.

Keep your make-up (reasonably) simple. My friend recently went on a date and when she went to the bathroom at the end of it she realized that her bright pink lipstick was all over her teeth as opposed to her lips. Not the worst thing that could happen on a date but still something to keep in mind when choosing your lippy for a big date :) Unless you usually wear elaborate makeup, a simple smokey eye and nude lipstick is always a great look.

What do you like to wear on first dates? Do you have any more tips to share?


  • Nice advice Pearl!
    Even though it’s been a while since I’ve been on a first date, I think your tips are great – they could also apply to the ‘meet the parents’ or ‘meet the friends’ situations in a new relationship xx

    • Thanks Caitlin! I’m actually turning this into a recurring column so I’ll make sure to cover a wide range of situations. Meeting the parents can be so nerve wrecking too…

  • Great advice Pearl! Being comfortable is the one that stood out to me the most- there is nothing worse than going on a date and feeling awkward + uncomfortable in what you’re wearing. Love outfit #2- looks fab! xx

    • Thanks Rachel. Yes I agree, being comfortable is the most important thing. Otherwise you just spend the whole time worrying about what you’re wearing rather than focus on your actual date. xx

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