Tick off the items on this checklist when you choose an outfit in the morning to ensure that you feel attractive, comfortable and appropriate for the day. The process sounds theoretical and time-consuming, but after a little practice, asking yourself these five questions becomes fast and intuitive. 

1. Are the colours and proportions flattering?  

Some outfits will be conventionally flattering, whereas others will sacrifice a little conventional flattery in lieu of an edgier or fashion forward look. Troubleshoot problem outfits until you are happy with the proportions. Most importantly, the outfit should reflect your figure flattering priorities. 

Check whether the colours work together and are flattering against your complexion.

2. Does the outfit map back to your Style Descriptor? 

My clients have a style descriptor, or a set of adjectives that describe what they want their style to convey. For example, client Meredith is a Playful Modern Classic who enjoys Bohemian, Bombshell, Androgynous and Retro touches once in a while. She wants to look tailored, playful, professional and approachable.

If you’re struggling with an outfit, think about how it maps to your style descriptor. 

3. Is the outfit right for the setting? 

Make sure your outfit is business casual if that’s the dress code at work. Or super casual if you’re off to the park with the kids. A little dressier if you’re going to the opera or theatre. Playful and creative if you’re going to an arty gallery. And fancy if you’re going to a formal wedding. 

4. Is the outfit weather appropriate?  

Taking into account the weather is of utmost importance. There is no sense in wearing a look that is too warm or not sufficiently insulating for the day. Dress for the elements.

5. Are you comfortable? 

Some days require extremely comfortable outfits because you’re moving around a lot and/or walking long distances. Others demand less physical activity and in these situations, you can probably sacrifice a little comfort. Being comfortable for the activities of the day is an important practical consideration. 

I have been focused on getting dressed in the morning, but this five question checklist is also useful during an outfit creation session like the ones I have with my clients. In this situation you are spending a bit more time and thinking about your style in general, so there are three additional questions you might want to consider. 

  • Is the outfit in your comfort zone?
  • Does the outfit evolve your style?
  • Does the outfit incorporate a little bit of now?

I mentioned these points in a recent post on ensuring that your needs drive your outfit creation process.

It’s not essential to satisfy every condition on the checklist, but satisfying as many of them as possible will increase your outfit happiness factor and boost your confidence. Then you can forget about your outfit and get on with the rest of your day.