How to Dress: Funky and Hip For Work

I’m having a great time tracking down answers for all of your requests! Here’s a good one from Rachael, that I think will resonate with a lot of you.

Here’s my request. I tend to be fairly casual and would live in jeans and t-shirts if I could. In fact, I work at a university where jeans are okay as long as they’re paired with something funky and hip because that’s the prevailing aesthetic. My problem is that I cannot figure out how to be funky and hip. I sometimes *think* I’m putting together a cute and fairly hip outfit, but I get to work and look like I walked out of a Lands End catalog. I guess what I’m really asking is how I can avoid looking so conservative without looking ridiculous. What is funky and hip and where do I get it? I see women in the hallways at work looking adorable, but I can’t figure out where they get these cute things. I must be shopping in the wrong stores. Maybe that’s really my request: what stores/catalogs/online shops might be the best for a funky and hip, but casual, aesthetic? I’ve tried Boden, but it looks too little-girlish on me and the sizing is often not right for my body (I’m a 14/16). Other suggestions?


This is a great question for a few reasons. First: The workplace has certainly seen a dramatic upheaval in the level of casualness now appropriate. But in certain professions and cultures (eg: media, academia and creative professions in general) I think fashion is playing a more important role than ever. Also: I think in some ways professionals are using their wardrobes to communicate authenticity and uniqueness in a way we haven’t seen since the late 60s.


Before we even get to clothing, adding a quirky flair can start with accessories. Do you wear glasses? If you do, there are so many options and fun frames that will update your look on an everyday basis. If you want to go for a Zooey Deschanel hipster style, there are a ton of frames to choose from.


Including these cute frames, which were designed by Zooey herself for Oliver Peoples.


Or you can go for this hip retro cat-eyed look from Kate Spade:


There are literally thousands of frames to choose from. The best thing to do would be visit your optometrist. They usually are experts at finding a pair of glasses that matches the style (retro, hip, funky) you like to the best color and frame for your face shape. For example, my eyes are a bit close-set, so my optometrist picks out frames that make my eyes look farther apart.

Next: Jewelry. A great necklace can perk up the most conservative outfit and make you look updated and fresh. When I was in Austin a few weeks ago, I noticed a few things. 1. It was incredibly funky and fun, and I’ve never seen more vintage stores. 2. I saw a lot of the following jewelry: delicate gold-tone necklaces with an edge and/or chunky natural stones.

Like this delicate horseshoe necklace from Alexis Bittar.


Or this necklace, by Kelly Wearstler.


Or this cuff, by Dannijo.


TJ. Maxx, Ross and Marshall are jam-packed with necklaces and bracelets like this right now if you are on a budget.

A bold, fun necklace or bracelet will punch up a plain black V-neck shirt and a pair of jeans like you would not believe.

Other accessories worth considering: scarves and handbags.


Let’s move on to clothing brands. Boden can be really, really cute and funky (and I find it is a favorite of academics, which is interesting) but the sizes can be weird and you’re right: it’s not for everyone. There are a few other chains that might be of interest.

I love Anthropologie. My friend is a size 14 and she does very well there, but you’ll definitely want to try the clothing on as everyone’s proportions are different. What I like about Anthopologie is the clothing looks unique and it definitely has a retro, quirky vibe. It can be pricey but look for sales. AND TRY CLOTHES ON that might not be in your comfort zone. I bought two jumpsuits there recently and I thought I would NEVER wear a jumpsuit, like, ever.


Bird Sweater, Anthropologie


Tunic, Anthopologie

Also, Modcloth may be of interest. They have really cute clothes, mostly dresses, in that funky, hip style you may be interested in. Online only, but you can return clothes easily for another size if you need to.

I LOVE this dress. It would be super cute and work appropriate with a cropped jean jacket or a cardigan.


Other brands to check out: Zara and H & M.

Finally, there are a number of fashion bloggers out there who cover what to wear in Academia. Here is a list of a bunch of them. Academichic was really wonderful, but they stopped blogging in 2011. However, it’s still worth a look.


Filed under personal style

7 responses to “How to Dress: Funky and Hip For Work

  1. I agree with Anthropology, great funky clothes that are unique yet classy. I always shop their sale racks. J. Crew also has some great unique pieces and jewelry. Thanks for sharing!

  2. Anthro is such a great suggestion. I get quite a bit of mine by shopping consignment and e-bay and participating in an Anthropologie trademarket on Facebook.

    As far as jewelry, I’ve found some amazing treasures at Goodwill, consignment shops, or antique stores. It means sifting through a lot of things that aren’t worth it and being able to spot a genuine treasure through tarnish, but I love my vintage pieces. One of my absolute favorites is a 1920s art deco lavalier that I found at an estate jewelry shop. Another is an antique camphor glass pendant. Definitely can change the whole look of an outfit!

    Thank you so much for all your awesome ideas! This is a wonderful series, and I’m enjoying every post!

  3. Gail K

    I’m a taller/bigger girl (size 12/14, height 5’11”) myself and I have trouble finding things that look good with my body type. I don’t have an Anthropology around me and have been inside one only once and found nothing that I would fit into or would work for my body type, but I could have just hit it at the wrong time. The same was true with H&M which looked like it was made for people much shorter and thinner than me.
    I’ve found that White House, Black Market has a lot of good options and you can shop online and return anything that doesn’t work out. Another good option that I’d found is Kohl’s. I can get a lot of the basics there (pants, shirts, etc.) plus they have a lot of designers who make affordable options based on the current trends.

  4. SRB

    I have the same brand of glasses in a similar style and I LURVE them. I’ve worn plastic frames my whole life and these hold their shape. Also, super cool.Worth the money!

    Oh, Anthropologie…why you gotta be so expensive?!?

  5. I am so honored that you answered my question–thank you! This is very helpful advice. I sometimes look at those large bracelets or slightly odd necklaces and then step away because I’m afraid to look cartoonish (or like I’m trying to be younger than I am). But perhaps if I’m wearing my usual casual outfit, the jewelry will work. I’ll give it a shot and report back on my own blog at some point (after a trip to TJ Maxx!). I will try Anthro, but I sometimes balk at the prices for things that don’t seem all that well made. It’s been a few years, however, and it’s time to try again. I do love their whimsical sweaters!

    So really, what you’re saying is be braver with the small things and the overall look will come together better than I think. I will go forth and be brave!

    Also: Gail K–we are very similarly built, I suspect. I’m only 5’9, but H and M and other hip kinds of clothing tends to fit strangely. I do go to Kohls, but even there, I end up looking more conservative than I intended. Strange phenomenon, indeed. I’ll try White House Black Market!

    • lavendel

      Wow, thanks for answering this question!!!! And thanks for asking it Rachael. Exactly what I was looking for help with too. I think I end up looking way older than I am because of the conservative look. And just don’t have the “knack” for figuring it out myself. Thanks, thanks, thanks!

  6. You cannot stress TRY IT ON enough! I am sooo glad I started saying why not to the things I wouldn’t have given a second glance.

    Don’t forget to step out of your comfort zone store-wise, too. Places like Cititrends have cool stuff in all sizes and are budget-friendly.

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