What to wear when you feel like you have nothing to wear

The feeling of "closet full of clothes but nothing to wear" used to curse me: I'd find myself standing in my closet, combing through the hangers, trying things on only to toss them on the floor while feeling like I needed to go out to buy something to solve the issue.

In the process of dialing back over the past several months, I started noticing that the pieces that I wear the most have a few characteristics in common:

#1 They're almost all neutral in color (navy, black, cream, white, olive, pale pink)

One of the reasons I gravitate towards neutrals is because I love to wear bold shoes, bags and jewelry. Basic neutral clothing goes with nearly every color and metallic tone, and has the power to balance unusual tailoring, a wild accessory, or hot pink lipstick. 

#2 Each piece has either a simple, slightly oversize cut, or has been tailored so it fits me really well

A simple cut means that a piece will stay relevant longer, and oversize means that it will be comfortable and have the ability to layer. The pieces I've had tailored (including jeans, believe it or not) are by default the most flattering, so obviously will continue to be pulled from the masses of other just-not-quite-right items.

#3 They're conservative, even if slightly offbeat

When I first started working at 22, I remember going out with my friends in a (fabulous) white (short) dress and subsequently bumping into someone from work. Immediately, I second-guessed my hemline and exposed shoulders and spent the next few months purging my wardrobe of college-era items and replacing them with pieces that needed to pass the test of "Would I be OK if I ran into my boss while wearing this?" That experience was a just-in-time reminder that my outfit choices send messages, and I wanted them to be positive and classy. Since then, the only "sexy" thing about my outfits have been my smile, wit and charm. (And occasionally shoes, but only with long hemlines, of course.)

#4 They tend to either look expensive, or truly were more expensive than other items in my closet

Neutrals in general tend to look more expensive, but pieces that exude investment are ones that are made of high quality fabrics and construction. Natural fabrics like silk, cotton, linen, wool and leather always look amazing if you take good care of them. My small collection of Vince silk blouses have been part of my wardrobe for years, and earn a lot of compliments. Buying them up on sale, in multiple cuts and colors, was one of the best wardrobe investments I made! A black wool Transit Par Such car coat bought at a D.C. consignment shop for $75 has been a staple in my fall/winter wardrobe since 2012.

#5 Almost every piece is versatile, with the ability to be dressed up or down

Versatility is actually a pretty easy quality to assess in a garment if you put a little bit of extra thought into it. Considering if a blouse or sweater would work with a suit, a pair of skinny jeans, a leather skirt, etc. and imagining it in your mind can help to quickly suss out a piece that will collect dust. If I had put this filter on most of my purchases in the past 5 years, I would have saved thousands. THOUSANDS! (Enter post on financial education that came a little later than ideal...)

Recognizing that there was a pattern to the items I wore consistently led me to start taking the time to identify each of these foundation items in my wardrobe (and donate the items that couldn't compete). It's actually very easy to proactively build outfits around these foundation pieces, because they're such a cohesive group that not only play well together, but also with my accessories. 

In previous posts, I've mentioned how taking iPhone documentation helps, and I'll repeat that again: the pictures in this post were pulled from my iPhone archive, and I used these reference photos to pack for a weekend trip to NYC and wore each outfit a couple of times this spring and summer! 

If you follow my Instagram account, you may have seen a post about my recent move. My new closet is about half the size of the one I left behind, a closet that Old Colleen would have abhorred and forced her husband to give up his closet to accommodate. Fortunately, I see this as a much-needed constraint that will help fuel my journey to a more minimalist wardrobe (and life). I'm currently in the process of ruthlessly cutting my wardrobe down to these foundation pieces only. When I'm done with this year of cutting back, anything new that I purchase will need to displace or upgrade an existing foundation element - meaning that I'll have to be extremely thoughtful in any and all investments.

That's all for now! Thank you for reading, I'd love to hear your thoughts on the key staples in your closet and any ideas on how to maximize space in my small closet while I'm in the process of pruning!