How To Wear Any Style (even if you’re broke, intimidated, or work in an office)

Wouldn't it be great if you could wear any style? Regardless of your income, mental space, body type, or workplace? The good news is: you can! Click through for body positive style tips and style advice!
Wouldn’t it be great if you could wear any style? Regardless of your income, mental space, body type, or workplace? The good news is: you can! I mean, within reason! Today Sally is going to teach us how.

What style of dressing are you most drawn to? Boho? Rockabilly? Classic? What style of dressing is the one you’d adopt if you had unlimited cash, unlimited time, a completely nurturing environment, and the ideal body shape to pull it off? Arty? Girly? Rocker? What style of dressing have you wished to emulate for years? What do you want to look like?

Now. Why can’t you look like that?

I’m not being cheeky, I swear! I want you to think about the barriers that stand between you and your this longed-for personal style. Consider what is keeping you from dressing, looking, and feeling the way you’ve always dreamed. Jot down a list. Seriously.

Then take a look at these workarounds. I’ve applied these, in one way or another, to the barriers that I’ve encountered on my personal stylistic journey. At this point, I’ve figured out how to live and dress around the roadblocks, and I look almost exactly the way I want to every day. But I’m sure there are obstacles I’m not thinking of, barriers I didn’t encounter myself, and I’m counting on you to shout out the ones I’ve missed.

6 Ways To Wear Any Style 

You think you can’t dress that way because you have the “Wrong” body shape

You want to dress like Joan from Mad Men, but you’re built like a granola bar. You want to dress like Agyness Deyn, but you’ve got curves galore. You want to dress like Michelle Obama, but you’re a shortie.

  • What key pieces can you appropriate? If you can’t go all-out-all-the-time, are there accessories, dresses, shoes, even styles of makeup that you can utilize so that you feel connected to this look?
  • What colors, accessories, and textures are key? Can you incorporate those into your daily wear?
  • Can you adjust this style’s signature silhouettes to your figure? Use belts to create waists, shorten hems to better suit a petite figure, pair specific bottoms with looser tops to accommodate a plus-sized figure?
  • Can you focus on details like necklines, footwear, hairstyles that fit into the style without adopting the look in its entirety?

You think you can’t dress that way because you’re Broke

You want to dress like Gwen Stefani and Victoria Beckham and Madonna. You want designer styles and loads of bling and everything of-the-moment. You haven’t a penny to your name.

  • Can you shop thrift and vintage, with a list of styles in hand? Seek out pieces that look just like the designer duds currently sashaying down the runway, but for a fraction of the price. Very little is actually “new.”
  • Can you DIY? Learn to sew, bead, embellish? Can you rip out pages from mags, create an inspiration board, and figure out how to recreate some of the simpler stuff yourself?
  • Can you stomach knockoffs? Can you shop Forever 21, Go Jane, and Aldo and be happy sporting a STYLE you love instead of a label you covet?
  • Can you borrow from girlfriends who own the duds you lust for?
  • Can you make do with wishlists and very slow accumulation of key items?

You think you can’t dress that way because you work in a conservative/intolerant environment

You want to dress like a rock star, a pin-up girl, a circus performer, a mermaid. You want to do your hair big and wear monstrous combat boots and pile on bangles from wrist to elbow. Your parents or teachers or boss or officemates or friends or lover will be scared/disappointed/angry if you do.

  • Can you amass pieces and tools that contribute to your look, but deploy them in small enough amounts that it feels like your little secret?
  • Can you learn to deflect biting comments by laughing with the commenter? “Hahaha, I know! Isn’t this WILD?”
  • Can you talk to a select few people about why dressing this way is important, so that you have some supporters amongst the dissenters?
  • Can you dress down Monday, Wednesday, and Friday and dress up Tuesday and Thursday? Gradually get your environment used to what appears to be an experiment until the time is ripe for full transition.

You can’t dress that way because you’re scared

You want to dress like Sarah Jessica Parker, Tilda Swinton, Sharon Stone. You want to break out of your rut, your shell, your feelings of boredom with how you look and dress and feel. But you don’t know who you’ll be if you do that, or if you’ll still like yourself, or if you can pull it off. You don’t want to be laughed at, or be disappointed in yourself.

  • Can you be gradual about trying the new style? Make your bedroom the testing ground. Get up 20 minutes earlier each morning and just PLAY in front of the mirror. Make yourself branch out just once a week.
  • Can you start by just wearing items from your coveted style around the house? Make sure you feel comfortable, love the look, have it honed so it feels like your own.
  • Can you wear one or two signature pieces at a time? Don’t go full-Carrie, just tack a giant flower to your blazer. Don’t wear a wiggle dress and bright red lips and a string of pearls, just strap on your Minna Parikkas with your simple sheath.
  • Can you take photos of yourself and look at them THE NEXT DAY? Get some distance and then evaluate. Learn how awesome you are one photo at a time until you feel ready to try out your new signature style in public.

You think you can’t dress that way because you just don’t have enough energy

You want to cultivate your boho side, polish your prep, rock out with the studs and leather … but you’re so danged tired all the time. School, work, the kids, your pets, your lover, the house, the car, and your social life suck up all your time and there’s nothing left for a makeover.

  • Can you talk to the important figures in your life about how important this is, and get their buy-in? That way, they’ll be more understanding when you aren’t around as much. They might even help!
  • Can you make this a priority? Something that you carve out one hour per day, or two hours per week, or a weekend a month to focus on? Every little bit helps. Spend that time making wishlists and inspiration boards, reading blogs and magazines, picking out the key items you need … and then, shopping!
  • Can you admit to yourself that changing your look might not take as much energy as you fear? Can you figure out what else might be preventing you from transforming your style? (See above.)

You think you can’t dress that way because you just don’t know how

You’d love to change. You know exactly what you want to look like, have the time, energy, money, and desire to make the change. But how will you put the pieces together? How can you keep your new, unfamiliar look consistent and true? How will it all WORK?

  • I felt like some of the advice was a little wonky, but have heard many stylish ladies sing the praises of the Lucky Guide to Mastering Any Style. This book outlines some iconic styles, recommends key pieces, and shows how to mix and match.
  • You can always ask your friendly neighborhood bloggers! Ask ME! Ask Imogen! Ask Angie! Ask absolutely any blogger who writes about style and fashion. We love you for reading our blogs, and the vast majority of us love to answer reader questions.
  • Trust yourself: Read, draw, take notes, experiment. No matter what any person or magazine may tell you, there is no wrong way to dress. Click To Tweet There is no wrong way to interpret a style. Go with your gut. You’ll be surprised how much your gut knows about fashion.

So, back to you. Have you found ways to dress they way you like, regardless of income/environment/expectations? If you have, share your tips in the comments so we can learn from you!

P.S. How to make cheap clothes looks nice + 13 ways to feel cuter and more confident

photo by Simon Wakaba // cc

15 Comments

Rio

This is one of my favourite posts of yours yet, well done!!! My problem is that I want to look like a million different people on different days! I'm lucky though, consistancy is not something required of a Student, and I have very understanding friends!

http://www.rioalexandra.blogspot.com

love love love xxx

Reply
Rachael

What a great post! I'm one of two people in my office who dress "creatively" – my other coworkers favor knit pants and bedazzled t-shirts – and sometimes it's weird having seven people ask me why I'm all dressed up on a Tuesday, but I truly feel more comfortable when I'm rocking my own look.

Reply
Mallory

Thank you for this post!! I've been realizing that I really need to mix it up and step outside of my neutral and solid color scheme haha.

Reply
ashe mischief

Great guest post, Sal! You totally hit the nail on the head with several of my own personal fashion issues, like time/laziness/fear and so much more…

Thank you, Sarah, for posting this!

Reply
emma

You know, you have really inspired me. I love vintage of all types, but I suffer from being EXTREMELY hard to fit- not tiny, but not plus sized, right in the middle, right before you hit plus sized, and kind of big on top-

Anyway, my wardrobe has gotten rather stuffy, and officy, and every time I had to get dressed I would spontaneously burst into tears. I felt so awful about myself, and I couldn't dress to represent me. It was rather depressing. I don't know why what you said here, hasn't occurred to me before now, but after I read this post I ordered a few things on Etsy, which came in yesterday, and fit LIKE. A. GLOVE.

I'm so so so happy, and today, from my desk, wearing a 1960s era mink collar and feeling rather glamorous, I thank you.

You're a doll. *says the lady wearing a mink collar**

Reply
Kristy

It is so interesting that I came across this post of yours today, as I totally stepped outside my comfort zone when I got dressed this morning and had to keep saying to myself "this is what X, Y, Z has worn to the office before, why can't I"

Reply
Claire

The biggest problem I have with dressing how I want to is the weather! It rains a lot where I am, and always seems to be colder than predicted. I'm always nervous about wearing something that can't be layered / easily taken off so I rarely wear dresses, and the puddles limit my footware.

Reply
Anonymous

I'm a little late to the party, but I found this post on Pinterest. You hit several of my limiting factors, but one that wasn't addressed specifically is age. I'll be 36 next month, and some of the styles I'm drawn to I feel I'm too old to pull off. Goth isn't undoable for someone my age, but pastel goth? I'm not so sure. Also, I think anytime you want to change up your look & start wearing something you aren't known for wearing, there is a fear that people will think you're trying too hard to be something you're not.

Reply

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