Transitioning to the Workplace: Bags and Shoes

My first ever law school summer internship was, simultaneously, a few other firsts: first full-time office job, first time in a formal office setting, and first job with a dress code. I was in my mid-twenties and had other work experience under my belt, but this was the first time I couldn't just wear jeans and a sweater if I felt like it. The internship was in a somewhat public-facing government-type setting, where something more formal than my current law firm's "casual business casual" dress code was preferable.

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In hindsight, I had no idea what I was doing. I wore many an awkward-looking and slightly too informal outfit that summer. I had a suit for the very formal interview, but once I actually got to working, I didn't have enough suitable items to rotate between trips to the dry cleaner.

To add a layer of complexity, that particular workplace ended up being a strange and disorienting initiation into the world of law: I was the only minority and almost every other person very matter-of-factly decamped to the Hamptons every weekend, often to their parents' presumably luxe vacation home. One fellow intern even appeared semi-frequently in the society pages at fancy galas. None of this is particularly common in the biglaw junior ranks, by the way, but I had no way of knowing that. Everyone else had a full closet of well-fitting business formal clothing and dressed accordingly, whereas I could barely scrape together daily business casual wear (which was technically acceptable, just not preferred). I felt so ratty in comparison that, to be honest, I didn't really try. That's not a recommended strategy for a full-time job or an internship that could yield a full-time offer (which this was not).

Ariana from the fantastic Paris to Go was kind enough to give my blog a shout-out when she wrote her very helpful post about the transition from college to the workplace. With that as my inspiration, I thought I'd do a series about the transition to working full-time, whether as an intern or an entry-level professional.

Note: My approach here is not minimalist and is rather inconsistent with helping someone build a pared down (and high-quality) personal wardrobe that they love. The primary goal here (1) is to accumulate an adequate work wardrobe quickly on a tight budget, that of a graduate student summer intern or recently graduated entry-level professional. Also, (2) my item suggestions lean towards the formal side of business casual, which for many white collar NYC workplaces means no jeans, but slim pants and somewhat causal skirts and dresses are okay. Both goals mean that the resulting work wardrobe may exist quite separately from what one enjoys wearing outside the office. The goal is to blend in and pick things that will not raise eyebrows while one is still getting used to the applicable wardrobe rules. Workplace norms in different industries and different regions of the US can differ dramatically. It's somewhat unlikely for many of these items to see much use outside of the work week. For today, I'm focusing on dresses, jackets and cardigans. For today, I'm focusing on bags and shoes.

Bags: Inconspicuous, Professional, and Functional

The goal here is to have something inconspicuous and professional-looking, that would escape notice even in a courtroom. I like totes that are large enough for whatever you may need to carry: files, a pair of shoes to change into at the office, maybe even a laptop. I prefer black over navy or brown, as I think black transitions better to whatever formal occasions one encounters at work. Many of the items here are, admittedly, pricier than a student or recent graduate might be comfortable with, but if there's room in your budget, a bag that might be carried every day and has some potential for utility in your non-work life is a good place to "invest" in a pricier item, if it is functional.

• Street Level Reversible Tote - $48.00 - A close friend carried this daily to her biglaw summer associateship and it was still in great shape at summer's end. She still carries it today. The brand also offers a larger, but less formal-looking reversible tote in black/brown. If it comes down to pleather versus, say, a fabric tote like the Everlane one below, I think pleather looks more formal.
• Everlane Twill Zip Tote - $48.00 - Fabric is not that common a material for work handbags and I'd worry about my laptop or papers if one is caught out on a very rainy day. However, the look of these is on point and the price is good. I've also had classmates who carried these to formal internships. If you need to carry a heavy laptop and a backpack is alright, Everlane's snap backbacks ($68.00) are functional, durable, and I think they look professional too. I'd prefer not to carry a backpack if formal meetings or court dates are on the agenda, though. 
• Longchamp Le Pliage Large - $145.00 - At this price point, there's a chance that it might be better to pay a little more for a leather bag instead, depending on local workplace norms. However, even if the price point here is not particularly summer intern or entry-level professional-friendly, the nylon Longchamp Le Pliages are worth considering because they're just so useful for both work and play (I sing the bag's praises here, for instance). If you can consider a higher price point, the monochrome Longchamp Le Pliage Neo ($185.00) is, arguably, more professional looking: I own one in black (the discontinued but identical Planetes tote). In your average NYC private sector legal workplace setting, the Le Pliage is an extremely common choice, so it blends right in.
• Madewell East-West Transport Tote - $178.00 - A leather bag might also be worth investing in, and the ubiquitous Madewell Transport line of totes will also put you in good company. I have, however, heard mixed reviews about the quality of the materials on the Madewell bags, mainly that the leather doesn't feel very nice, so Cuyana ($175.00) might be a good alternative. One colleague carries the Fossil Sydney tote ($168.00), which is a bit more formal and has a zipper.

Shoes: Reasonably Comfortable, Probably Boring

Finding shoes for the workplace can be difficult. The good news is that, as a result, there is a broad range for acceptable footwear, even in settings as formal as court. So long as the shoes lean towards the classic looking side of the fashion spectrum in a neutral color (generally black), it's all good. I have  bad luck with shoes; few pairs hold up to frequent wear for longer than three months if I wear them while commuting. It's likely best to have at least two pairs to cycle between. It's actually hard to make specific recommendations because I'm not loyal to particular styles. I generally follow the same "rules" or guidelines for my shoe shopping for both work and play: I gravitate towards leather flats that are in the $55-$75 price range when on sale (shoes that started at the ~$100 price point). I like Sam Edelman and currently enjoy the Louise et Cie pair I have (similar).

I have trouble finding suitable pumps or wedges at my target price point, so I tend to spend ~$110 on those. I often stick with Cole Han though there's a surprisingly long break-in period. Boots (such as my beloved Sam Edelman Petty booties, which are going strong as of the end of their second year of frequent wear, including on commutes) tend to be pricier still. My recommendations below, however, are mostly shoes that are closer to my price range for flats. 

• Payless Karmen Pump - $29.99 - I loathe pumps and only wear them for interviews, so these might even be the best value for me, even if these are not real leather. I have a friend (and her firm colleagues) who swears by these for daily wear indoors in a more formal office. I think she sometimes wears them to commute as well, though she prefers comfier shoes for that.
• Target Emma Flat - $39.99 - I've thought about getting these on and off on the recommendation of a few college classmates, but never got around to it. They're genuine leather, which is nice. I don't have high expectations of the lasting power and durability of flats because the way I walk causes them to wear out extremely quickly. 
• Louise et Cie Fable Flat - $64.47 (sale) - These are similar to a pair I own. Mine are comfortable, with fairly soft leather that didn't take too long to break in. They're holding up alright for the past few weeks, but I avoid wearing these outdoors and commute in other shoes. There's another plainer-looking Louise et Cie flat also on sale. Nordstrom and other department stores likely always have a decent selection of sale flats in black leather with a reasonably professional look, though it's hard to know which brands or styles are best without trying them. I often end up with Nine West or Sam Edelman shoes. 
• Naturalizer Oath Pump - $39.99 (sale) - Many of the pumps I've owned in the past are from brands that primarily market themselves as comfortable shoe brands skewing towards a older audience. I even did most of my clerkship interviews in a pair of patent pleather Naturalizer pumps. These do have a strange fabric-looking detail on the edges of the upper upper, so I'd prefer a similar design that omits that detail (not yet on sale) or a similar shoe in another brand. 

Did anyone else have an adjustment period or difficult transition at a first job, whether an internship or a full-time position? Do you have any favorite work-appropriate bags or shoes in a student or recent graduate-friendly price range?