How to dress appropriately (while being completely neurotic)

I have an over-developed sense of appropriateness, especially as it relates to clothing. Two questions are always on my mind: What is the appropriate level of dressiness for the occasion, and what is the appropriate clothing for the weather/temperature/venue? After almost 20 years of marriage, my husband has learned to ask what I want him to wear before putting on clothes, because apparently changing once you have on an outfit is a hassle on par with, say, having to wrestle a 2-year-old into a full-length snowsuit and boots.

I think this has its roots in my deep desire to belong, or at least to look like I belong. My nightmare isn’t showing up at school naked; it’s showing up at a company Christmas party in what I wore to work that day and realizing everyone else stopped at home on the way to change into nice dresses.

My nightmare isn’t showing up at school naked; it’s showing up at a company Christmas party in what I wore to work that day and realizing everyone else stopped at home on the way to change into nice dresses.

This also translates into judgmental tendencies toward both myself and others who are dressed wrong. (“Who cares that you think you wore the wrong outfit?” says husband to me often. “Just forget about it and enjoy yourself.” To which I reply: “Do you know me at ALL? The ability to let things go is not one of my spiritual gifts.”). In my defense, it’s not just me. This is also something I have in common with my closest friends. A common exchange:

Of course, wearing the right thing means owning the right things, because you can’t just dash home and change if you don’t have the item in your closet. So for this post, I decided to share some accumulated wisdom from my friends and me on what constitutes an Adult Woman’s Appropriate Wardrobe for All Social and Professional Occasions.

A quick aside: “Hey!” I imagine males protesting. “What about us?” This blog is intended for any and all genders, but this post is specifically for females because an Adult Male’s Appropriate Wardrobe for All Social and Professional Occasions is ridiculously simple (see earlier remark regarding the advantages men have over women).

Men need 26 items besides their everyday wardrobe. Want to know what I think those are? Sign up to get an email whenever I post, and I’ll send you my list of 26 items that comprise an Adult Male’s Appropriate Wardrobe for All Social and Professional Occasions.

So. Now that we’ve taken care of those identifying as males – ladies, here’s a list my friends and I curated of the building blocks of an Appropriate Wardrobe. Much of this is for women who work outside the home, but my SAH friends, there’s stuff here for you, too.

Note that I’m assuming here that you already have a solid everyday wardrobe for work or outings with friends. This is what you need besides that:

• 3 interview outfits. Unless you’re in finance or law, you can probably get by without a suit nowadays, but you should have 3 business-friendly dresses, or skirts with dressy tops. Think simple and sleek – nothing too wild, too patterned, too ruffly or girly, too over-the-top. You want them focused on you, not your outfit. If you want to wear wilder stuff, save it for after you get the job. 

Why 3? Because when you nail the initial interview, you need something to wear to the second- and third-round meetings most companies do.

• A funeral outfit. It happens … and more often than you think, sadly. The good news is, this can be the same as one of your interview outfits.

• A formal dress in a timeless style. You may only need this once or twice in your life, but it’s almost impossible to find in a moment of need without paying crazy prices. Comb the sale racks at your leisure, find a classic black formal dress or the like, and stash it away. Bonus points if it’s stretchy enough to accommodate fluctuations in size. (Important point from friend BB: “I’d clarify that ‘formal dress’ means more cocktail and less prom.”)

• 2 dressy coats – one lightweight and one winter. You find the perfect dress, you shave your legs all the way to the top, you get a blow-out and a pedicure … and you’re going to wrap all that in the same puffer coat you wear to the grocery store? This is another instance where the sale rack – or even better, the thrift store – can be your friend. My winter dress coat is a black faux fur I found at Goodwill that makes me feel like a queen. My spring/fall one is a fun black/gray check I found at an end-of-season sale for 70% off.

• Flat-soled dress shoes or wedge heels. Outdoor wedding, team event in the boss’ backyard, graveside funeral service. You don’t want to be teetering around, prying up your heels from the lawn with every step.

• 2-3 pairs of dressy shoes and sandals you can wear all day on a concrete floor. I’m the cheapest person ever when it comes to clothes – 98% of my wardrobe is from thrift stores and clearance racks. But the one thing I spend money on is shoes. At the big annual trade show my company participates in, I’m standing on concrete from 7:30 a.m.-8 p.m. I pack 3 pairs of cute-but-comfortable shoes (changing them each day gives your feet a break) and a footcare kit that includes Epsom salts, moleskin tape and Band-Aids. Favorite cute-but-comfortable shoe brands: Toms, Clarks, Born, Vionic, Ecco, Naot, Dansko, Fly London. These shoes will cost you $100-$300, and they are completely worth it.

• A work-event friendly swimsuit and cover-up. It is a hard fact that you should be able to wear whatever you want, including a small bikini to the team gathering at your boss’ lakeside cottage, without people throwing shade. It’s also a hard fact that once you see your coworkers mostly nude, you can never unsee them (and vice versa). I own a one-piece and cute coverup, plus a pair of board shorts and water shoes in the event some boss takes it in their head that white-water rafting or some such activity would be good for team-building.

• A decent robe. This was also courtesy of friend BB, who noted rightly, “You just never know who might see you. Like, you don’t want to be outside with the neighbors, watching the firetrucks attired in a torn sleepshirt.”

• A decent umbrella. NOT a freebie.

• A nice work tote. Most days I carry an IKEA backpack, but twice a year I have a board meeting at my college with a group of people who wear suits and diamond rings the size of my head. For those situations, I pull out my Stuart Weitzman heels and my fuchsia leather tote.