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Wardrobe Rehab: How To Choose 'That' Dress

Outfits May 29, 2015

How To Choose 'That' Dress

Have you got ‘that’ dress in your closet? You know the one, it feels so good to wear you can’t help but pull it out pretty much every week, knowing it will be the best bet when you’ve got no time to plan or haven’t a clue what to wear. In fact, you wear it so much that your friends are like, oh yeah, you’re wearing that dress again, and you aren’t even offended because it’s so perfect (and wearable) you don’t care. Hopefully you know what I’m talking about, if not these probably sound like the ramblings of a mad woman. But if you don’t have a dress like this in your wardrobe, it’s time to start looking!

As a bit of context, I bought a black dress about 5 years ago which has been my ‘that’ dress ever since. In all honestly it was pretty unassuming (see it here), but the fit was just so right that I’ve probably worn it weekly for 5 years. I even tried to get it copied but the end result was a bust.

I’ve been wanting to find another such dress recently (time for an upgrade!), but was a bit stumped, until I chanced upon this  white dress. I kept it to wear in Santorini for the first time, but am pretty sure it’s going to become a weekly wear – I’d be wearing it tonight if it wasn’t in the wash!

Wearing: Club Monaco dress, J Crew flats, Celine Bag, Athens hat

Wardrobe Rehab: How To Choose ‘That’ Dress

This got me thinking, what makes some clothes, like this dress, infinitely wearable compared to other pieces in your wardrobe? What turns them into ‘that’ dress or ‘that’ skirt? Let’s just say I got a bit obsessed with this idea while I was travelling. In the end, I think it comes down to how a dress makes you feel – which is a combination of factors about what it looks like and how it makes you look.

And so, I thought I would share a few factors for finding your next infinitely wearable dress. A few pointers for your next new dress. Perhaps if we followed this advice all the time, our closet would be full of ‘that’ pieces and we’d be overwhelmed with choice every day, instead of sometimes staring into our closets blankly!

How to choose ‘that’ dress

Pick a fit that emphasises your best points

This is key, and pretty obviously really, but you’d be surprised how often we buy pieces that don’t quite suit us, or bring out our best assets, just because we love some element of their design. Finding a dress that flatters you in every way generally comes down to the cut and shape of the dress – over time I’ve realised that the ‘fit and flare style’ which is fitted to your bust and then flares out is the more flattering on my body shape, so it’s a good idea to work out what suits you too. Naturally if you feel great you’ll wear it all the time!

Choose a supportive style

There’s nothing better than a dress that requires no rooting around in your underwear drawer for the right bra. This is particularly applicable for those gals with medium to large boosies (count yourself lucky ladies with little ones!). For me, dresses that have become absolute staples have been ones that a) I only need a simple t shirt or balconette bra or b) I don’t need a bra at all because the dress has built in support. The latter is definitely better. ( . ) ( . )

Decide on an appropriate length

A dress that gets worn all the time is one that is appropriate for a multitude of situations and occasions, so when you’re searching for that dress, it’s best not to get one that’s too short or too long. The more versatile the better! ‘Appropriate length’ means different things to different people obviously, so it’s going to be a personal call, but a great and adaptable length (for me anyway) is just above the knee.

Think about colour

Naturally you want to choose a shade or pattern that’s not going to date in the next half decade (hopefully that’s how long you’ll be wearing it!). For your ‘that’ dress, it’s ok to lean on the safe side when choosing, perhaps picking a prime colour that suits you and isn’t too trend driven.

Match it to your life

A dress that you wear over and over is inevitably one that matches your lifestyle, where you live and the things that you do. For example, if you live in a really cold climate it’s unlikely that a light summer dress is going to become a staple in your closet, and the same can be said for heavier dresses in warmer, sweatier climates. I’ve barely worn all those gorgeous wool dresses I bought when I lived in London!

If you’re looking for a few ideas when it comes to picking a dress you’ll wear over and over, here are a few of my faves:

$ Nasty Gal, Topshop, Nastygal, Topshop, 6 Shore Road.

$$ Zimmermann, Club Monaco, Lover, Serena & Lily.

Do you have a dress you wear and wear and wear? What style is it? And how did you find it? Here’s to clothes we wear over and over!

Photos by Airlie Walsh

Stay tuned for my guide to Santorini next week…

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