Life & Style Made Simple

Welcome to "Ask Rosie"! 

If you're a newsletter subscriber, you likely know that I ask you to share your wardrobe frustrations with me. I find your responses so incredibly helpful, and the amount of guilt I have over not having time to respond to each email has grown so much over the past couple of years! So, I decided to do something about it in a manner that will benefit all my readers.

Over the years I've received so many similar questions, so I wanted to share my guidance all in one place. The fact is, while we are each different, many of us experience the same challenges. You are not alone!

I will continue to add new questions to this page. If there is something you'd like me to address, please email me at

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Capsule Conundrums

My biggest wardrobe issue is that I need two complete wardrobes, work and home. I want to look pulled together after work, but have to be able to be active and get dirty, so can't wear my work clothes at home.

I used to have to dress far more conservatively for work, so I understand how it can be frustrating to basically maintain two closets. 

I'd take stock of how many hours you spend at each activity you do during any given week, and assess whether your wardrobe is made up of similar percentages. Most likely, you like don't need as many clothes for your time at home as you do for work. It also sounds like looking into clothes by activewear companies that also make streetclothes like Patagonia or Athleta could be good for after work, because they are made with active people in mind. You can still look put together after work but won't have to worry as much about getting your clothes dirty. 


Whenever I get a capsule organised if I don’t include formal wear, I’ll have heaps of social events to attend and nothing in my capsule to wear. 

Frankly, I say don't worry about the capsule and wear the clothing. Your capsule doesn't have to be so constraining. It can be really hard to know three months in advance whether you are going to have a lot of events requiring more formal attire. I'd focus on creating a mini capsule of formal wear to keep on hand in addition to your regular capsule. The size of the capsule may be dependent on the season, as holidays and summer seem to have the most formal events, but do what works for you! 

I know my response isn't mind-blowing, but I believe in creating a wardrobe and capsules that really work for you. For some people, functional capsules work better than seasonal - you create your own rules! 

I love prints but I can't figure out how to mix them in to a capsule wardrobe.

I completely believe that prints can be part of a cohesive wardrobe. If your prints often have different color schemes, I do suggest trying to narrow down the prints you choose to 3-4 colors schemes, each including a grounding neutral. If there is overlap in the colors, even better. Then, when you shop for solid items, select pieces with colors contained in the prints you own or buy. You should be able to mix and match a bit better this way. 

For example, let's say you have two dresses with mostly different colors in them, but they both have teal. A sweater or scarf in teal will go with both dresses, even if the rest of the colors are different from each other. 

For winter, look for sweaters, jackets, coats, tights, etc. that echo or coordinate with the neutral (or closest thing to one) in your patterns. This will help your outfit look cohesive. Keeping neutral basics that contain the neutrals in your prints really up the versatility.

Closet Cleansing

My issue is updating my wardrobe and keeping a capsule. I'm trying to get rid of what I don't need and stop buying what I think I need.

It sounds like what you "think you need" may not actually be what you need? Seems like a good idea to pare down on your wardrobe then spend some time wearing and tracking your outfits/wardrobe to help you assess what items truly would make your wardrobe work better for you.

We are all different so what works for someone else or is a "must-have" or "basic" for someone else may not work well for you or your wardrobe at all!

I highly suggest signing up for the free Closet Bootcamp to help you cull your wardrobe. Once you've done that, take a few weeks to track what you're wearing using the tracker from this post. A few posts to help you know what to do next are linked at the bottom of that post.

I have way too many clothes but can't bear the thought of getting rid of them. At the same time, my overflowing closet keeps me from knowing what to wear each day.

You will feel so much better after you have weeded out the clothes you don’t love and aren’t wearing. It can be a really daunting task. If you haven’t done so already, sign up for my Streamlined in 7 closet bootcamp, which will guide you through your closet clean-out. The emails break down the clean-out over a week, but you can wait and do you closet in one day, or do bits and pieces as time and energy permits.

Most people have concerns about getting rid of so many clothes:

  • What if I need it/want it in the future?

  • What if I am left with nothing to wear?

Well, if you truly think an item is something you will need in the future but you aren’t wearing it now, then hang on to it for a bit and set a reminder for a few months from now to check back in about the piece. Really consider whether it suits your style, your lifestyle, and your figure.

Having fewer clothes may cause some anxiety at first, but you weren’t wearing or loving the pieces you’re getting rid of anyway! You’ll be left with the pieces you love and wear, which will feel freeing. Also, be practical as you weed out. If there is something you wear all the time because it is functional but you don’t love it, keep it for a while until you can find a replacement for it that you love.

It's really hard to let go of items even when they don't fit right.

I hear you - it is so incredibly difficult. We have spent money and time on them, and sometimes lots of love, too. It's also difficult when the clothes don't fit us now but we hope they might in the future. 

Personally, I know that wearing clothes that fit me right now makes me feel good. Seeing the others in the closet causes stress! I remind myself that I may not even want to wear them if and when they fit again. And, if I know they'll never fit quite right, I think about how there is likely someone out there with a different body shape who will love them!

I love this quote I read in an article about the museums in Italy:  “If the changes are real, they will meet resistance. If everyone likes them, they’re false.” It is natural to meet real changes with resistance. 

Maybe try a baby step? Pick a piece you're hanging on to that doesn't fit anymore. Make notes about what you like about it and why you purchased it. Donate one piece, and see how it feels! 

I've worked really hard to downsize my wardrobe and I'm finally loving it! Shopping is a big part of my life, though, and I find it hard to stay away from the stores. I constantly find myself wanting to buy wardrobe additions.

 I completely understand this. It's so hard to put a hold on shopping when it's something you love to do but you don't need more clothes. It sounds like you have done a great job creating a wardrobe you love.

If you still want to head to the stores, use them for inspiration. Keep an eye out for how the stores are styling the items and see if you can copy it with the clothes in your closet. Or, if there are one or two pieces each season that you think would be a great addition to your wardrobe, go on the hunt for those. Look for the best option you can find and make it a challenge! 

If you want to take a break from the stores, make a list of other things you can do that will be a treat for yourself to take up that time.

Stymied by Style

Help! I have no idea what my style is and I don't know how to figure it out.

I think finding your style is the hardest yet most important part of creating a wardrobe that really suits you. If you haven’t done so already, create a style board on Pinterest and pin outfits and pieces that you really love to it. Look at magazines and blogs for inspiration, too. TV character wardrobes are also a really great place for inspiration because the stylists on the show have worked hard to develop distinctive styles for the characters.

Once you have a board with 30-50 pins, spend some time analyzing the pins. Write down any of the following that you see multiple times on your board:

  • Outfit combinations

  • Individual pieces

  • Colors

  • Patterns

  • Outfit proportions

  • Accessories

Pick your favorite 5-10 pins and write down the first few words that come to mind for each pin. Do these words describe the style or look you’re going for?

Try to recreate some of the looks you like from the pieces in your closet. Don’t worry too much right now about whether you have the specific pieces - you’re just trying to test out the looks a bit to see how you feel in them and whether they feel like “you”. Sometimes looks we love on others don't really make us feel happy. What changes could you make to the look to make you feel happier about it?

Continue this process until you have really narrowed down what feels good to you and makes you feel confident in what you’re wearing. Don't get too caught up in figuring out your "style type". While these groupings (classic, bohemian, feminine, preppy, etc.) can be really helpful at times, it's also easy to feel confined or boxed in. 

I want to upgrade my look but don't know where to start.

I know “upgrading your look” can be daunting. The first thing you must do is figure out what that phrase means to you. What is the look you’re striving for? Can you re-style some of the clothes in your closet to achieve this look? If not, are there a few pieces that you can add slowly to get you there? Pinterest is, of course, a great resource for finding the looks you want to be wearing and figuring out how to style your clothes or finding which pieces you may need to add to accomplish your style goals.

It may also help to find some style icons who dress the way you want to look. How do you describe the style of these women? What kind of pieces do they often wear? Is there a repeating cut or style? Do they have any uniforms or outfit proportions they seem to stick to? All of this information can help you figure out how to upgrade your look.

Upgrading your look is an evolving process. Try picking the top three pieces you think you need first to transition to a new look and start with those. 

Life Happens!

I have so much going on in my life right now that I can't really focus on my wardrobe. At the same time, I know looking good will make me feel less stressed!

Here are a couple ways to deal with those insane times before they happen:

1.) One thing you can do (if you're up for it) to minimize a bit of stress is to select three outfits you feel good in that work for most days of your life. Keep them together in your closet so you don't even have to think about it next time you need to get dressed but have too much other stuff going on to spend more time and energy than you have figuring out what to wear. 

2.) Pick one or two go-to outfits for each facet of your life: work, evenings out with friends, date night with your partner, weekend errands, etc. Take a picture or make a note of each outfit and place it somewhere you're guaranteed to see it. Use these outfits as a fallback when you just don't have the energy to make a decision. Try to make sure these pieces rarely sit in the laundry hamper for days on end. 

I'm in the middle of having kids so I don't want to invest in an in-between wardrobe.

I completely understand not wanting to invest in a wardrobe during the years you’re having babies because you body goes through so many changes! Sometimes price is not an indicator of quality. When you are shopping, focus on whether the item was well-made. Does the fabric retain its shape when you stretch it? Does the stitching looks strong and and secure? Do the buttons or zippers lie flat without bunching or pulling?

I truly believe you can find good quality items for a decent price. Also, there are so many second-hand shops popping up on line these days. Definitely look into places like Thred-Up, where you may be able to find more expensive clothes at a great bargain.

I'm transitioning from a very casual job to an office. I need a whole new wardrobe but don't have a lot of $$ to spend on it!

First, congratulations on the new job! Is the dress code formal (suits) or a bit more casual with skirts, dresses, and slacks? Since you're new to the company, take some time to get to know the office a bit to understand what you really need. A written dress code may be very different from what people actually wear.  

Kohls, Target, and Macy's have great options for work wear that won't break the bank, especially because they have sales so often. Focus on simple pieces that all work together. Even your interview suit can be made a bit more casual by wearing them as separates, so think about how you can wear new pieces with the suit. 

Fit Frustrations

My biggest problem is fit. I have a lot of clothes that I like but aren't always flattering. I wear the pieces that fit well over and over - is there a way to make the rest of my closet work better?

Fit is so incredibly important. I have to admit that I'm so lazy when it comes to taking things to the tailor, but if you own pieces you love but the fit is a bit off, consider seeing if they can be adjusted to mirror the fit of the pieces you routinely wear.

If the unflattering pieces just won't work no matter what, I recommend taking stock of the pieces that fit really well. What about them makes them fit so well? Darts in certain places? The length? Note the fabric, construction details, measurements, etc. so that when you are looking for new items to fill out your wardrobe you will know what to look for. And, of course, get rid of those pieces that don't work once and for all!

I recently lost a lot of weight (and still losing) and now I have nothing to wear. I always said if I was skinny I'd have a killer wardrobe...I need to find a new style... The old one is forever gone!

WOW. Congratulations! You have worked so hard, and I am so thrilled for you. Trust me when I say I know how difficult it is to make this commitment to yourself and to stick with it. 

I can see how it is both incredibly exciting and also overwhelming to have this new fashion world opened up to you. But, you are in such a great place because you can completely create your new look and style. 

Since it sounds like you're still losing weight, you'll want a balance between finding clothes that fit now and finding ones that will still work a handful of months from now so you don't have to continually purchase new items. If you wear skirts and dresses, it makes it a bit easier because their fit is less precise than pants. Look at items that wrap or that can be worn tighter and looser. 

Usually, the mantra is "buy the best you can afford." While you should still buy well-made clothing since it fits better, now is not the time to invest in that luxurious cashmere coat. Save your money for now and focus on a few staple items that will get you through the next set of sizes. 

I now have a wardrobe in size 10 and 12 when I currently am wearing a 14! I'm working on losing weight again, but I know it will take a while.

I know it's so hard to shop for the size you are right now when you don't want to stay there. Consider looking at 5 really mixable pieces in a size 14 so that you feel good right now? With three tops and two bottoms you can create quite a few outfits after mixing in shoes and layers that work at different sizes. 

In my experience, having clothes that are tight makes me feel worse and doesn't really help me get back down, but everyone is different.