December Wardrobe Challenge: Dressing up


Can you believe it's December already? Time for a second round of the Wardrobe Challenge series. Before I get into this month's topic here's a quick recap of what this series is all about and how to participate in the challenge:

The basic idea of the Wardrobe Challenges series is to use the annual cycle of events and seasons, from the beginning of fall to the summer, as an opportunity to examine our wardrobe from one particular angle each month. Each monthly wardrobe challenge will consist of one theme, a set of questions to think about and a few small assignments that you can casually do throughout the month. The challenges won't require a structured, hands-on approach - instead, the idea is to really get you thinking in-depth about a certain overarching aspect of your personal style or your wardrobe and help you prepare for yearly events, like the holiday season or the beginning of summer. If you want to participate, I recommend you read through the questions and assignments at the beginning of each month, but don't try to answer them straight away. Print them out or carry them in a note on your phone and then gradually, throughout the month, add your own ideas and notes.

The theme for December is ... dressing up. There's really no better time to examine your own definition of 'dressing up' and 'dressing down' than December, the holiday month. Weeks of parties, events and special occasions, but also of family time, relaxation and reflection.

Your idea of a dressed up vs a dressed down look is a super important component of your unique personal style. An outfit I might call 'dressed down' might be a special occasion look for someone else. What might be statement piece for me, could well be a basic for you. Your definition of what qualifies as dressed up and what doesn't runs through every aspect of your style: from your style concept to your ideal wardrobe structure and of course your daily outfit choices. Use the 13 questions and two assignments below to become more aware of your own personal level of 'dressiness' and how you express that level through your outfits.

Basically, there are three separate factors to consider:

  1. How dressed up vs down is your overall personal style?
  2. How do you express whichever level of dressiness you are going for? Which elements of your look do you amplify or tone down? Make up, colours, textures, fit?
  3. What is your range of dressing up? Do you wear really bold looks one week and super casual ones the next or do your outfits tend to stay within a relatively narrow range?

A side note: The second factor is especially interesting to me, because it seems to be quite a cultural thing. I once read that a defining feature of the typical French style is a small range: women never really dress down, they are always properly dressed, but also never go all out and prefer an understated look, even for evening events. In the UK it seems to be the other way around: Most people get really dressed up for parties, but you also see quite a lot of people in pyjamas at the supermarket ;) Have you noticed any cultural patterns like that?

Here's the full set of questions + assignments:




 On a scale of 0 to 100 (very casual to super dressed up) where would you place your own personal style? Who are you comparing yourself to? Your friends, colleagues, bloggers, celebrities?


 If you had to choose between the two, would you rather be a chronic over-dresser or a chronic under-dresser? Why?


 What is the most dressed up outfit that you can build with your current wardrobe?


 How similar are your most casual and your special occasion looks, i.e. what is your range of dressing up?


Can you think of a single element that could turn one of your regular daytime looks into a special occasion look with minimal effort? High heels or a bold lip colour for example?


What do you prefer to shop for: special occasion stuff, lounge wear or daytime clothes? Are either of these groups over- or underrepresented (compared to your lifestyle) in your wardrobe as a consequence?


What are you more prepared for: an unexpected invitation to a black-tie event or a whole weekend spent lounging indoors with friends?


 In the past 6 months: What was your most dressed up and what your most casual outfit? Now consider the occasions you wore them to: Were they equally fancy and casual, respectively?


 Is there sometimes a disparity between your beauty look and your outfit, i.e. do you wear no to minimal make up but eye-catching outfits or vice versa? Or do you like to match your beauty look to your clothes?


 What elements do you usually amp up when dressing up your look: colours, details, make up, hair, fit, textures, etc ? Which do you keep relatively constant?


 How much contrast do you prefer there to be between the individual items of your outfit, i.e. do you like to pair statement pieces with neutral basics or do you tend to create looks using items of a similar level of dressiness? (check out this post if that all sounds confusing)


 Are you happy with both your overall level and range of dressing up vs down? If not, what factors are preventing you from implementing your ideal range/level? Practicality issues, confidence, job requirements?


 Are there any elements in your style concept that you only wear for special occasions?



Develop a fail-proof special occasion look for last-minute invitations. Think main items, shoes, jewellery, bag, make up and hair. Aim for a look that you can put together in less than 15 minutes.


 Practice calibrating your outfits. Start out with one of your go-to looks and then one-by-one amp up or tone down its individual elements, e.g. add, remove or change your make up, add or remove accessories, tuck in hemlines, switch out your shoes, add a different jacket, etc. Take notes and snap a few pics to refer to later.


*image via Stylizimo