How to Wear Flats in the Winter

How to Wear Flats in Winter | CorporetteIn cold weather, what are the best ways to wear flats to work? With socks? Tights? Reader E wonders…

Could you recommend some ways to style flats for the winter? In years past I have worn skirts and opaque tights with pumps or booties in cold weather (I don’t live in a particularly cold climate), but earlier this year I decided to give up on heels altogether because of some foot problems I’ve been having. I’m happy with my flats for summer looks, but ballet flats just look so odd with tights to me. I’m hoping for some better style ideas! What flat shoes work best for winter looks? Thanks!

Great question, Reader E — and even though it still feels kind of warm outside, the cold will be upon us in no time. (Winter is coming!) We’ve talked about wearing flats all the time, as well as interviewing in flats, but not in a while. Obviously you can just wear flats where you would have worn pumps, but if you can’t walk in flats with tights (I can’t!), or if you feel like something is off with the silhouette, then we need to dive a bit deeper.  I’m curious to hear what readers think, but here are some of my thoughts:

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Shopping Category Killers

shopping-category-killersHave you ever bought an item so perfect that you just don’t need to shop for anything similar any more?  As in, the whole shopping category is just no longer one of your concerns? Did you KNOW it would be a shopping category killer when you bought it (i.e., the clouds parted, trumpets rang out, etc.) — or was it just something you fell in love with more and more as you had it?

In my own wardrobe, for example, I’ve seen it happen mainly with accessories:

  •  My dangly diamond earrings and right-hand diamond ring:  every time I see something similar I think, nah, if I’m looking for something sparkly and fun, why would I wear anything but my dangly diamond earrings and right-hand diamond ring? (I discussed both in my post on the best splurges I’ve made on products.)
  • A heavy black wool wrap from Henri Bendel:  this one I didn’t even like that much when I bought it, because super lightweight pashminas were very in at the time.  I needed it for something specific, though, and it was on sale for around $150, so I bought it.  I’ve proceeded to bring it to pretty much every wedding, every fall/spring evening out, and on every vacation I’ve taken since. I’ve bought other scarves and wraps in other colors, but my Bendel’s one has stood the test of time.
  • My Cartier watch — I’ll admit, I have bought other watches since the Cartier, but they never get worn.

I suppose there are other items here also where I’ve been so happy with the purchase that, when the item inevitably wears out, I just buy a new version instead of researching the area again.  Spanx Higher Power tights… Fantasie bras (4510 for the win!), Weitzman Poco heels…

Readers, what purchases have been YOUR category killers?  Do you have any regrets on the initial purchase?  Were you surprised it became a category killer for you, or did you buy it hoping it would be the last X you’d ever buy?  (For example — I love my dangly diamond earrings and right-hand diamond ring, but they were both a whim purchase, spurred in part by a sale — if memory serves the earrings were around $1000.  I’ve worn them so much and will continue to do so that I kind of wish I’d splurged a bit more! But the need for “more” isn’t so great that I need to buy new earrings (if that makes sense). On the flip side — were you disappointed in any purchase that you had hoped would be a category killer? 

Psst: in the past we’ve talked about shopping habits like spreadsheets and “crop rotations,” as well as the best places to shop online.

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Are Skirts and Dresses Unprofessional?

Are Skirts and Dresses Unprofessional? | CorporetteAre skirts and dresses unprofessional? What if you have a boss who has a firm opinion, one way or the other? What if you have a boss who forbids YOU from wearing dresses and skirts, when other women in the office can and do? Reader A wonders…

I recently started a new job in a creative industry, and our offices are officially business casual but usually just regular casual. My boss hates that I wear dresses and skirts. She told me that looking feminine in the workplace is bad for careers and she only wants me to wear jeans or khakis if she’s in the office and I can only wear skirts when she travels. I’ve abided by it for a couple months since she was really persistent about it, even though other women in the office wear skirts. I’m confident that my skirts are not inappropriate length wise, they’re standard work skirts from Macy’s and Lane Bryant. Nothing ruffly or lacy either.

Anyway, my manager is leaving the company, but now I feel insecure about my clothing. Is it a bad move to wear skirts and dresses several times per week?

Wow. Honestly, your former manager sounds super annoying — particularly given that other women in the office wear skirts! I can only assume it’s a personal problem with you (something about your style irks her) or she is being sizeist, whether consciously or unconsciously. (The other possibility I thought of after Googling Reader A’s email address: The manager felt threatened professionally by Reader A, who already has an established, successful career — and wanted Reader A to look less managerial.)

Whatever the issue: I’m sorry you had to deal with it, and I’m glad the manager is on her way out. We’ve talked before about when feminine clothes are unprofessional, as well as how to look professional in a business casual environment where the guys are in jeans and hoodies, but not all at once. So let’s discuss.

  • Know your office. You say other women in the office wear skirts — how are yours different, if at all? Are you wearing them with much higher heels that you wear with pants? Are the women who wear them in different roles than you are (for example, much more senior or much more junior/administrative)? Reading office culture — and fitting in — is an important part of your job. You don’t have to give up your entire personal style, but you do have to learn when to play it safe — years ago we had a successful goth lawyer guest post on this very topic; we also recently discussed how clothes are only “empowering” if they actually help you get power. Without seeing your office it’s hard for me to make suggestions, but when I hear “creative business casual” I think of a shirtdress with flat boots, for example, or a sheath dress with a jean jacket and a scarf instead of a cardigan. We’ve talked about how to transition a conservative wardrobe to a casual office before.
  • A feminine style is one thing; being in costume is another. This doesn’t sound like it’s an issue with Reader A, but I’ll mention it briefly. If you tend toward a more girly style — A-line skirts, high heels, full makeup — you may be crossing the line from “dressed up” to “in costume.”  Particularly be wary of more vintage styles for the office.
  • Start slowly. Since you’ve been abiding by your manager’s weird “rules,” the office may perceive this as a style change — so start slowly. Wear one dress a week, not all dresses. See how people react, what comments you get. On the days that you aren’t wearing skirts or dresses, dress up your pants outfits as well — wear a blazer with jeans, or a feminine cardigan with khakis. (Some of our advice on dressing for a promotion may help bridge the gap between your jeans wardrobe and your dress/skirt wardrobe.) If you have a favorite pair of shoes you wear with your skirts or dresses, wear them with your pants and see how it goes.
  • Get an honest second opinion. If after a few times of wearing a dress you still feel uncomfortable, talk to your HR department or a more senior colleague you trust to give you an honest opinion. They know your former manager, your office, and you, so they may be able to give you better insight here.

What are your thoughts, readers? How would you handle this (now, as well as with that manager) if you were in Reader A’s shoes? Do you think dresses and skirts can be unprofessional?  

(Pictured: Hollywood 819, originally uploaded to Flickr by Jessica Hartman Jaeger.)


N.B. These substantive posts are intended to be a source of community comment on a particular topic, which readers can browse through without having to sift out a lot of unrelated comments. And so, although of course we highly value all comments by our readers, we’re going to ask you to please keep your comments on topic; threadjacks will be deleted at our sole discretion and convenience. Thank you for your understanding!

Law School, Orientation Outfits, and Dressing For You

Law School, Orientation Outfits, and Dressing For You | CorporetteHow should you dress for law school orientation? When you’re planning which outfits to wear, how much should you worry about looking professional, or put-together, or about making a good first impression? Reader N wonders…

I am extremely excited to be starting law school in the fall but I am puzzled by the idea of picking orientation outfits. Any suggestions?

Congratulations, Reader N! I still have such fond memories of law school, and we’ve covered a lot of things about it here, such as what to wear for mock trial competitions, which bag is best for law school casebooks, hornbooks, and of course your laptop. We’ve even talked about how — if you’re shopping for clothes before law school — your money may be best spent on interview and work attire. 2Ls, 3Ls, and recent grads: Anyone care to write a guest post on what bag is best these days, as well as any other tips or tricks for marrying the digital world with the study of law? For example: Did anyone like reading cases on Kindle or taking notes on an iPad (or, gah, an iPhone)?

ANYHOO: I’m sure I worried about which outfit to wear to orientation, but I couldn’t tell you what the heck I wore if my life depended on it. I was only two years out of college when I went to Georgetown, and honestly I don’t even think anything had occurred to me as not being “work-appropriate” (beyond a super short corduroy miniskirt that one of my older editor friends had pulled me aside and told me was not appropriate). Some of the older students had already formed conservative work wardrobes (particularly those who were coming from years on the Hill); others maybe just had a preppier style.

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The Corporette Guide to Stylish Cardigans for the Office

stylish-cardigans-workWe shared our first Corporette Guide to Cardigans way back in 2010, so we figured it was time for an update — and the timing is just right for those of you who freeze in your air-conditioned offices during the summer, or are shopping for easy layering pieces for the fall.  We’ve talked about how how to button cardigans for work in the past, as well as how to buy seasonless cardigans.

Ladies — which is your favorite KIND of cardigan to wear to the office? Do you have a favorite brand or style that you keep buying, or have stocked up on recently?  What are your biggest struggles with finding stylish cardigans for work, or styling them to look appropriate for work? 


stylish cardigans for office1. Banded. These cardigans have some banding at the bottom and (usually) on the sleeves, which makes their shape a bit blousy or boxy. They can come with a matching shell for a twinset look, or be worn by themselves with, for example, a button-front shirt or blouse, or a nice tank or tee (such as the cardi pictured, Saxxon Wool Cardigan, available at Brooks Brothers in nine colors for $148). Because these kinds of cardis have their own shape, they’re less than ideal for wearing with dresses, and, for our $.02, best with pants. Ideally you want full-length sleeves so that you can easily wrap it around your neck if you need to — that said, three-quarter length sleeves are very popular, such as this Halogen cardigan (20+ colors, regular, petites, and plus sizes, for $27-$56). If the twinset is very boxy (think a more Jackie O cut), then they can be worn over your shoulders, almost like a cape. Other examples: reader favorite Supima Cardigan at Lands’ End ($19-$89, a zillion colors and prints, regular, petite, and plus sizes), reader favorite Charming Cardigan at Talbots, $19-$99, this merino cardigan in 12 colors for $39 at Uniqlo, or this J.Crew cashmere cardigan (16 colors!, sizes XXS-XXL; pictured at very top). One of my budget favorites has always been August Silk — look for them at spots like TJ Maxx, but Amazon also carries them, as does Macy’s.

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Exposed Zippers, Shiny Fabric, Sharkbites, and More: What Do You Hate?

hated-workwear-design-detailsWe haven’t talked about your most hated design details for women’s workwear in far too long — so I thought today it might be a fun open thread. I know readers were recently talking about their hatred of exposed zippers (which I agreed with several years ago, but I guess I’ve been worn down by their omnipresence — the exposed zipper is everywhere!), and many of shared their hatred of unlined pants for a while now.

For my $.02:

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