I often allude to feeling some anxiety about dressing more cheaply than many of my peers, and sometimes feeling out of place, "too poor" for this profession. It's madness, because I grew up privileged and never wanted for anything. I just don't come from the kind of background so many of my peers and colleagues seemed to (given, say, how more than half my cost of attendance for undergrad was covered by need-based financial aid). This worry isn't a big part of my day to day life. In the end, I'm reasonably comfortable wearing my J.Crew Factory suits to court and to interviews, and it's all turned out fine. That being said, because I've never been discerning enough to tell the difference between a cheap and expensive suit on anyone else, and because I've never tried on a suit more expensive than Ann Taylor, there's always a part of me that wonders whether other people can tell. I'm confident it's never cost me a job or anything, but this is a profession that values conformity to expectations and rules more than most.
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So my answer to the this question, which came up recently on "TLS" (the primary internet forum for law students), might be surprising. It's a firm no for women in NYC biglaw. No one will judge you for not having expensive clothes or handbags, provided that items fit you reasonably well and are appropriate for your setting (dress codes and levels of formality can differ quite a bit by firm). I've never been given any real reason to believe my occasional anxiety about this topic is well-founded. I had a hard time with my first-ever law internship because I simply didn't have enough work-appropriate items, and I ended up feeling very self-conscious about how my attempts to "make do" didn't quite work, but since then, I've not had any real problems. Some might assume that at the biglaw income level, there's an expectation to wear expensive clothes all the time, but that's definitely not true. Most of us are far too busy to pay attention to what anyone else is wearing, unless it's standing out in some glaringly obvious way.
The answers people gave largely conformed with my understanding, that the price of the items in your work wardrobe is not a thing to worry about, and that people only notice things that stand out, and generally only because they're not appropriate for the particular dress code culture of the office. Other fashion-conscious individuals might pay a bit of attention to something that looks very snazzy, but that's generally just to notice that their colleague is fashionable and has good taste.
The suggestion of getting a nice watch is a bit off base, at least at the firms I've been at, where most junior associates don't wear or notice each other's watches (the fanciest one I ever noticed was a Shinola). Someone more senior is just as likely to be sporting an Apple Watch, with the silicone sportband no less, or a Fitbit, as anything else. I myself am partial to Skagen, either the larger Anita or the smaller Freja.
The $50 handbag price OP mentioned probably won't get you a leather bag at retail, but can definitely buy a suitable professional-looking faux leather tote. If one is willing to step up a bit in price for leather in the under $200 range, the Fossil Emma tote is fairly affordable, and I've also heard someone vouch for the Cuyana zipper tote. For non-leather professional-looking bags in the under $200 range, one will always fit in with the large Longchamp Le Pliage in black, gray, or navy, or the black Lonchamp Neo. Note that, outside of one's time as a summer associate, when there are frequent social events, or when one is headed to court or off-site meetings, few people will ever see your handbag except when you're on your way in or out of the office for your commute.
The $50 handbag price OP mentioned probably won't get you a leather bag at retail, but can definitely buy a suitable professional-looking faux leather tote. If one is willing to step up a bit in price for leather in the under $200 range, the Fossil Emma tote is fairly affordable, and I've also heard someone vouch for the Cuyana zipper tote. For non-leather professional-looking bags in the under $200 range, one will always fit in with the large Longchamp Le Pliage in black, gray, or navy, or the black Lonchamp Neo. Note that, outside of one's time as a summer associate, when there are frequent social events, or when one is headed to court or off-site meetings, few people will ever see your handbag except when you're on your way in or out of the office for your commute.
My one concern about OP's post was their mention of how they generally relied on business formal-looking things from Zara, not so much because of the price point, but because, in my experience, it is harder to find a well-fitting, definitely work-appropriate item from Zara than from other brands that cost about the same, or only slightly more (Ann Taylor, Banana Republic, J.Crew with their frequent sales, J.Crew Factory, and in the past, Loft). I have a basic blazer from Zara that I really like. It somehow fit perfectly, was affordable, and is made of a softer fabric that is comfier than most, but I'm fairly certain that's a rare find. So I'd likely encourage OP to shop more from one of those standard mall brands for workwear. One also finds the occasional piece from Uniqlo (like the smart style ankle length pants) or Old Navy (like that ponte blazer). And of course, there's always the (probably better) option of shopping secondhand. Thredup always has a robust selection of J.Crew and most of the other workwear brands. Certain arguably "fancier" brands like Tory Burch or Diane von Furstenberg can be found for more J.Crew-like prices at TheRealReal.
One other thing I'd be concerned about with business formal from Zara is durability. K and I have found that some suits don't hold up that well to frequent wear, even if trips to the dry cleaner are kept to a minimum. As I mentioned in a discussion with Archana, even pricey men's suits (his primary interview and court suit is wool from Brooks Brothers, nicer than anything I own) don't necessarily hold up well to only occasional wear over several years. I had thought my collection of older all-synthetic suits (mostly Ann Taylor Seasonless Stretch) was holding up extremely well, though more recently, I've noticed a rip where the shoulder attaches to the sleeves in one jacket. Previously, the only problems I've ever had were with jacket linings, which do tear with frequent wear. Granted, I don't have any direct experience of whether something from H&M or Zara would do worse than something from Ann Taylor, but the lesson I take from this is that suits are more fragile than one might expect. Spending a bit more upfront may be a good idea for something that absolutely must look presentable, and for which the need will come up with unpredictable frequency.
One other thing I'd be concerned about with business formal from Zara is durability. K and I have found that some suits don't hold up that well to frequent wear, even if trips to the dry cleaner are kept to a minimum. As I mentioned in a discussion with Archana, even pricey men's suits (his primary interview and court suit is wool from Brooks Brothers, nicer than anything I own) don't necessarily hold up well to only occasional wear over several years. I had thought my collection of older all-synthetic suits (mostly Ann Taylor Seasonless Stretch) was holding up extremely well, though more recently, I've noticed a rip where the shoulder attaches to the sleeves in one jacket. Previously, the only problems I've ever had were with jacket linings, which do tear with frequent wear. Granted, I don't have any direct experience of whether something from H&M or Zara would do worse than something from Ann Taylor, but the lesson I take from this is that suits are more fragile than one might expect. Spending a bit more upfront may be a good idea for something that absolutely must look presentable, and for which the need will come up with unpredictable frequency.
Certain other categories are particularly good for "saving" on, such as shoes for wearing around the office, because so many office-dwelling women commute in sneakers or boots and switch shoes at their desk. There are several biglaw associates out there who swear by the Payless Karmen pump, if you're so inclined. I do think people are better served by shoes that are comfortable for walking in, which for me, often means spending a bit more (mostly Cole Haan and Sam Edelman), but one generally only needs fancier shoes for walking within the building, from office to conference room. Court appearances and off-site meetings can be rare for junior associates, so there's not as much need for one's more formal-looking shoes to "travel" well. Still, the need could come up, so I value having walkable formal-looking shoes. For me, that's the Sam Edelman Petty booties in fall/winter and the Cole Haan Tali bow flats when the weather is too warm for tights. The former are comfortable for a whole day of walking, but the latter are only good for a half day.
Do people judge each other for what they wear in your profession? I assume that NYC law and finance-type offices are some of the most conservative and formal anywhere in the country, with the possible exception of Washington D.C. (though I imagine the rules of professional dress there are slightly different, and maybe a bit more conservative).
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