Avoiding Fashion Disasters, Work To Flirt Outfits and Dating Tips From A Guy

Updated: Oct 23, 2018

What do you find it harder to dress for: work or a date? Last week, we focussed on how to create your own work uniform. This week, it’s all about dates! Dates can be a real styling quagmire: daytime vs evening dates, things to avoid, and (our hardest) how to go from the office to a date.

Daytime date outfit

Our Enty Stylists Hollie and Maiken show us exactly how to pull off daytime outfits that would be perfect for a date. These two would be ideal for a casual lunch date or a weekend activity. Wearing some jeans with a pair of comfortable heels or a skirt with boots will make it look like you have made an effort for your date yet are still dressed appropriately.

Evening date outfit

Enty Stylists Elenice and Jessica nails the evening date look consistently. Depending on where you’re going, a bodycon dress and strappy heels will dazzle your date. If you’re heading to a more relaxed location but still wish to dress up, you can not go wrong with a pair of jeans, your favourite blouse and some heels.

Fashion Disasters To Avoid

  • Ambitious outfits — keeping it simple will more likely lead to outfit success, and allows him to focus more on you rather than the spikey see through shirt you are wearing.

  • Dressing for the wrong kind of date — get a firm idea of where you are going so that you don’t turn up to go sightseeing wearing your best cocktail dress.

  • An outfit that requires sucking in — you want to feel comfortable on a date, and wearing something that involves sucking in and trying to reshape yourself will lead to both of you feeling awkward.

  • Exposing yourself — it can be nice to sometimes show off some of your best assets to wow your date, but only do so if there is no chance of accidently flashing them. Be conservative yet sexy with your outfit choice, leave something to the imagination ladies. (If you need tips on dressing conservative yet sexy, see our blog post on the topic).

From Work to Flirt

Picking an outfit that’s suitable to wear to work and then straight to a date can be a real conundrum. The trick is to pick clothes that straddle the serious and the flirtatious. Here’s an outfit that could easily take you from Day to Date.

Shop The Look:

ASOS, Wrap Top

Topshop, MOTO Jamie Jeans

If you can’t wear jeans to your workplace, swap them for some trousers:

Reiss, Tailored Trousers

ALDO, Court Heels

(See The Day to Date Pinterest Board)

How To Be Single Podcast

There is more to dating than just picking an outfit, and sometimes we need to have a good old laugh about the good and bad of being single! The Debrief podcast discusses how being single can be great, how it can also sometimes be hard, and gives you useful life tips. It will also make you burst out loud on your commute to work. You can download this episode here.

Totally unrelated but we love it anyway

Have you ever wondered what advice a guy would give a girl on dating? Look no further ladies. Matthew Hussey is a dating guru when it comes down to cracking boy code and what their strange texts actually mean. His YouTube channel discusses topics such as how to tell if he really likes you and wowing him with confidence. But, take his advice with a pinch of salt ladies, after all the most important thing on a date is to be yourself.