Dating Outfit inspriation

By Gem - 10:10:00

Are you unsure about what to wear on your next date? Well, this is my dilemma at the moment. I want to look elegant, sophisticated, and confident. I want to convey some personality with my clothes but not seem too over dressed. Tricky stuff!
I'm fairly new to this dating malarkey and it's a minefield of etiquette and brings a whole host of stress and worries. It seems very American to me and it was easier when you just met people at parties or on your course but I'm getting older now and apparently going on dates is a thing us oldies do. Anyway, I digress... I spend ages deciding what to wear for work and have it hung up the night before so you can imagine the panic I get in trying to pick something to wear on a date.

Here are the two looks I've chosen for very different date settings:

dinner date

The dress is from the Little Mistress Curvy range and is perfect for a dinner date or meeting at a bar after work for a midweek date. I would wear this to work with a cardigan and tights but ditch those in the evening and put some jazzy pumps on with them. This bag from Hushhush is big enough to fit my make up in for a touch up before the date but still chic and smart.

casual date

My second outfit is something I will pretty much be wearing this weekend for a date where I'm going to be walking and having lunch in a country pub. I'm pretty obsessed with Fred Perry at the moment (my instagram feed is full of FP eBay bargain buys) and this dress is making it's way to my house as I type. The Miss Selfridge parka and Dr Martens complete the mod-esque look and are also very practical. You could swap the parka for a smart black coat for a cinema date or exploring the city on weekends.

I know we all want to look our best and impress our dates but it's not a good idea to wear something that makes you feel uncomfortable. So I try to wear something which makes me feel cool and confident but most importantly, like me.

Do you find it hard to dress for a date?

  • Share:

You Might Also Like


  1. Well I'm one of those long term relationships but when I did date it's a right minefield you're not wrong. Girls aren't the only ones who sort their outfits out the night before, I've always done that. Eliminates stress for sure.

    Cheers for the comment on the festivals, I've only been to Wales twice even though I don't really live that far away. Sounds cool, I've not heard of it. Thanks for stopping by the back, have a nice weekend.


Thank you for leaving a comment, feel free to ask me any questions here or on twitter- @Gemma_DS.