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For some reason, weddings make me overthink my outfits. I think it's the feeling of someone else's judgmental aunt sizing me up in front of the shrimp platter that leads to self-doubt and paranoia over dress code references on invitations. It shouldn't be that way, but it's part of the wedding tradition, right up there with picking China patterns and listening to the maid of honor talk about the couple-in-question as if no one in the room has ever experienced love before.

Over the past several years, I've been to enough weddings to realize that there are some basic formulas to hitting the dress code expectations while still being true to your own style. I've also realized there are really only three types of wedding dress codes, or three "levels" of dressiness with the most stringent being black tie, then formal, and finally cocktail which I designate as "anywhere you would have a cocktail" which could include anything from a boat to a tailgate. 

Here are the formulas that I've employed in dressing for each of those levels of wedding dressiness this year using things already in my closet.

#1 What to wear to a black tie wedding

The above photo is what I wore to my friend Alyssa's black tie wedding in NYC. It's a simple black ballgown skirt with a silk / cotton blend blouse and nude heels, a combination that I landed on by considering the question "What would Jenna Lyons wear?" while perusing my closet. 

Jenna would not wear Rent the Runway. Instead, she would wear something undeniably fancy, with an unexpectedly understated piece, in simple colors. Black tie doesn't necessitate a gown or a full-length skirt, but it does require a key element of your outfit to be fancy enough to not be upstaged by your date's cumber bun. What, might you ask, are pieces that compete with cumber buns? Think ball gown skirts, feathered dresses, beaded blouses, tailored tuxedo pants, and anything taffeta. If you've got that key piece, the other elements can be simple and even unexpected to keep the look true to your style. 

#2 What to wear to a formal wedding

This is my favorite type of wedding dress code, because it still requires you to be fancy but with less stringent guidelines than black tie. Meaning, it's more fun! With a formal dress code, I can find ways to make my cage heels appropriate such as pairing them with a vintage red silk dress I picked up for $10 at my local Logan Square thrift store (there used to be a gold metal seashell sewn on the bodice, and chopping it off with a pair of nail scissors was the only "tailoring" necessary). 

When dressing for a formal wedding, I think of what fabulous people wear to an art gallery opening and dress accordingly. You want to look classy, with a twist. Look for items that keep your shoulders or knees covered, and add spice with accessories.

#3 What to wear to a cocktail wedding

A cocktail dress code is more casual, and the perfect opportunity to wear a matchy-matchy silk pantsuit like the one below. Or, that amazing embroidered pencil skirt that's been sitting in the back of your closet for four years because you're not sure how to style it. Or, that basic little black dress you've had forever with a pair of bold shoes. Shorter hemlines, bare shoulders, fancy flats and other indicators of comfort fair game. I like to imagine what flappers of West Egg wore to Gatsby's parties and dress accordingly.

I think the most difficult variations on these three levels of wedding attire are seasonal: what to wear to a black tie wedding in winter is a harder question (with the answer always including "add a fur stole"), as are the variations tied to the odd disclaimers added to cocktail attire wedding invitations intended to control weird relatives (such as "no jeans" which should be obvious to all invitees but then seeds doubt in your mind as you imagine your silk pantsuit dancing to Stevie Wonder, completely out of place in a sea of bedazzled Wrangler jeans).

Any thoughts on wedding attire rules that I've missed? And tips on dressing for winter weddings? I'd love to hear your thoughts on what to wear to a wedding while still honoring your personal style.

Vintage stores have kept me from dropping out of my challenge to not buy anything new for a year, and it is about time that I wrote an ode to my undying love of everything vintage. Whether you're currently an aficionado of legitimate grandma clothing or not, I guarantee you that spending 25 minutes browsing through the racks of a great vintage shop will lead you to some great discoveries (and soul searching about what's in your closet that would pass the test of time in the same way).

Without further ado, here are my top five things to hunt for on your next vintage shopping spree:

#1 Statement jewelry

Although I wear the same simple gold and silver fine jewelry almost every day, occasionally mixing it up with statement pieces is something that I love to do - and nearly all of my statement jewelry is vintage because it's affordable, unique and timeless. Every time I browse through a display of vintage jewelry, I'm amazed at how the same trends reappear decade after decade.

The key is to look for pieces that are a little offbeat, but still look and feel like a quality item. Avoid plastic pieces and tarnished metals and instead hunt for enamel, Lucite, glass, and natural materials like amber, stone and even bone.

When I was in Prague, I found an amazing carved bone bead necklace for $60 that became the perfect piece to wear with a simple long maxi skirt or spice up a tee shirt and pair of jeans. 

#2 Silk scarves

There's a store in the Wicker Park neighborhood of Chicago (called Una Mae's for local readers) that is my secret source of silk scarves: they have a $5 bin that has fed my collection for a few years now and I get more use out of a silk scarf than most things in my closet: I use them for a wide range of purposes including spicing up a basic black crew neck, to tying my hair back, packing statement jewelry into pretty rolls in my suitcase, and tying around my wrist or to my tote to add a little je ne sais quoi!

Key is to look for 100% silk in crisp colors, without fading or stains. Avoid polyester - they don't look nearly as nice when tied, and they snag!

#3 Leather and fur pieces

There is no better source for affordable, sustainable 100% leather and natural fur than your local purveyor of vintage clothing. My absolute favorite leather pencil skirt is vintage, and it is one of the top pieces in my fall and winter wardrobe. (And, it was less than $20.) For years, I've lusted for a shearling fall coat but couldn't bring myself to spend $2,000 on one. This summer, I found the perfect one at my local vintage shop in Logan Square… for $19. That's right, folks, a 100% suede and shearling coat for literally 1% of the cost to buy it new. (OK, and $30 to have it professionally cleaned, if I'm being honest.)

#4 Quality blazers

Nothing irritates me more than a cheap blazer. There is just no need to own a cheap, polyester, ill-fitting and overpriced blazer when there are literally oodles of 100% wool, silk, and linen ones with beautiful pearl and tortoise buttons just waiting to be discovered on the racks of a treasure trove of old used clothing.

My absolute favorite blazer is a black wool and silk blend that surely cost some cute grandma a lot of money back in the day, but with a little spare cash and some tailoring it is like my second skin for work. Definitely competes with my run-of-the-mill collection of Brooks Brothers suit blazers.

#5 Boots

My addiction to all things vintage started in college, back at the BEST of the BEST vintage stores in Champaign, IL (shout out to Ivanka and call to action in making sure this place still exists…) called Dandelion Vintage. There, I found the most amazing pair of eel skin cowboy boots that are still my favorite nearly 9 years later and earn me compliments from fashionistas and respect from cowboys everywhere. The fact that I bought them on my college budget says all there needs to be said.

Again, looking for leather and quality construction is the key.

Ok, that's all I have for you this week. Would love to hear about any of your top vintage finds and anything that's missing from this list!

(Special thanks to Becky Howe for these fascinating photos of me perusing old clothing...)

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!