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Ask Sherry: How to feel your best even when you don’t feel you’re pretty

You asked, and I am answering every Friday once I have enough questions!

You can ask any question using the form here.

Have you read, “Your Money or Your Life” by Dominguez and Robin?

Yes, it’s on my list of The only personal finance books you will ever have to read.

An excellent book. I ought to re-read it for some frugal inspiration.

What are some simple things I can do to feel pretty even when I’m feeling frumpy and fat?

Well I’m sorry to hear that you do have those days, but truth be told, I do too. Who am I to lie and pretend everything is rosy when it isn’t?

So I understand.

I hope it’s temporary and doesn’t last long.

Here’s what I do:

  1. Wear Colour
  2. Smile (even if you don’t feel it)
  3. Stop reading magazines, social media, blogs and watching TV that makes you feel bad
  4. Get naked
  5. Make better choices
  6. Listen to great music
  7. Wear matching undergarments (it does work)

In detail:

1. Wear Colour

Wearing colour in your wardrobe, like with a really pretty necklace (I really like this simple but heart lightening necklace under $50), great shoes like these ones in a pointed rose gold (shoes ALWAYS FIT unless you’ve just had a baby…. :\ ), or wearing a very feminine watch like this one that makes me smile:

Or just a very pretty cashmere sweater in a bright colour like this peacock blue can do wonders. Or a great striped colourful scarf like this one, or a fantastic purse that makes your heart sing each time you hold it like this red leather hobo!

Accessories always fit, is what I’m trying to say, like my now beloved boots that really make me feel good when I wear them:

Another way to wear colour is to wear makeup. I feel so drab and listless at times that if I just do my makeup (face powderconcealer, eyeliner, highlighter, blush and some satin pretty pink lipstick), my entire mood changes. I feel and look more polished; I stand up straighter and prettier even if my outfit is drab.

If I did my hair, I’d curl it too and try to do something with it.

Fragrance can also help, I spritz on my favourite smell (lavender essential oils mixed with clean warm cotton, or any of these replica beachwalk or replica fireplace scents), and feel much better.

Try pick out at least 3 things you love about your body and highlight those areas. For instance, I really like wearing clothes that are looser where I feel slightly off, and items to showcase what I think are my best features (e.g. my legs, my neck, my wrists).

Everyone has problem areas (as dictated by the fashion elite), but there’s no need to dwell on them.

At least, it does for me. Believe it or not, sometimes I feel like I am not quite as stylish as I could be given my wardrobe and there are some days I don’t quite feel comfortable in my body (for whatever reason), and colour or a great accessory is one way to boost my feelings about myself.

2. Smile

Everyone looks better when they smile. Everyone looks prettier, warmer, and the whole world really does smile back at you when you smile at them. We all have resting bitch faces (men included), and a smile can change all that.

Even if I don’t feel it, smiling makes me feel better… and it boosts my mood because it tricks my body into thinking I’m happy. It makes me happier as a result, and studies have shown that fake smiling does work. So does fake laughing.

What might help is googling cute baby otters, they do make me smile as silly as that sounds. Or listen to a great comedy (like comedians in cars getting coffee).

Part of smiling is also helpful when you know what you are grateful for. It is hard when you feel fat and frumpy, but there are things worse in life than looks, such as having all your working limbs, a healthy, functioning body and all five senses

3. Stop reading stuff that makes you feel bad

Go on a detox.

Toss and stop subscribing to those magazines.

Stop reading bloggers or looking at photos that make you hate your body. Just for a little while. Or, find great style bloggers who are more like you and get inspiration from them. I love Franish’s post on this, being an average woman in a warped fashion world.

They’re all airbrushed, remember? Remember that guys aren’t really into skinny women anyway, at least, not the super skinny bony kind (I am sort of that body type), and it is not attractive. I don’t have nice curves that bigger women have, a butt, a chest, or anything curvy. Most guys I know, like curvy, bigger women. REAL women. Who eat. Who aren’t Amazonian supermodels.

Sure, they love to ogle them, but there is a reason why Marilyn Monroe in all of her curviness was such a healthy role model for beauty, and the best video I have recently watched is:

Love your body. Own it. There is good and bad in every one and every body. Focus on the good.

4. Get naked

This one sounds strange, but taking a shower and taking the time to really scrub your body to get rid of dead skin flakes, washing your hair slowly and massaging your scalp, and lathering on lotion while your skin is wet can brighten your mood.

I love a really good warm shower to make myself feel better and lift my mood. Nothing invigorates like a shower.

Getting naked, also helps because if your clothes are ill-fitting and cutting in the wrong places, it can create problems that don’t actually exist. When I wear mid-rise pants, I get this muffin top flab that hangs over my jeans and makes me feel like I’m Shamu… and that is just ridiculous, so I have donated and sold all of my mid-rise pants (there’s still one pair I can’t get rid of), and switched over to these comfortable, soft, huggable high-rise jeans as my go-to pairs.

When you don’t have tight, ill-fitting clothes on, you will realize your body is not as big as you think. I have that feeling each time I feel like this, and when I go to take a shower, I realize that I’m quite slim and skinny. Badly-worn or ill-fitted clothes just make me feel otherwise at times.

5. Make better choices

If you are just FEELING this, but don’t really think it about yourself, the above tips will help you the way they have helped me.

If you feel like you could do some work in gaining muscle tone, losing weight and changing your style, then start doing something about it.

Make better choices shopping, start with The Curated Closet for some guided help (excellent book on finding and rocking your own personal style).

Make better choices with your eating habits. I recently noticed my pants not quite buttoning up and I realized the weekly pastry was not helping, so I cut it out of my routine and am increasing my activity/fitness level slightly by doing yoga at least 3 times a week (I love this Gaiam yoga app to guide me through (my review of it is here)):

I am also starting to consider doing a little more cardio and some weights, but that’ll come after I get a yoga schedule down.

I started making, LITTLE, TINY changes to my eating habits; smaller portions, being less greedy, and saying “no” for the first time, to second servings.

I also don’t drink pop or sugary drinks because I’d rather eat a huge slice of cake than drink it in a can of watery, sugary pop and not feel satisfied in any way. The trick is that I can tell that I am feeling like I am not quite myself and not fitting in my favourite items, so I start taking action immediately instead of waiting or buying bigger clothes and seeing the problem get worse and worse.

I’m only masking the symptoms, not treating the cause of my weight gain if I don’t treat it now.

6. Listen to great music

I find what also helps change my mood from being down and feeling fat & frumpy is listening to really fun music that makes me want to dance (and I do!), because it re-affirms that life is beautiful and no one is looking at me as harshly as I am looking at myself anyway.

As of late, Baby Bun (mostly Baby Bun) and I have been addicted to this song on repeat:

Isn’t she a fantastic singer with a killer bod?

7. Wear matching undergarments

I know it sounds trite, but wearing stuff that is PRETTY, COMFORTABLE, and MATCHES (holy trinity) can do wonders for feeling great, at least it does for me. I really like the brand Cosabella, and they make plus-size products that I hear really do hold up, are comfortable, pretty and make you feel great.

Their best sellers are their lace bras (minimal padding and VERY comfortable, I own two of them) Black lace bra (plus-sized version here). They also have the padded version if you are so inclined.

I don’t know about you, but I am not keen on wearing anything that doesn’t actually look like underwear, but bears resemblance to shredded string (what’s the point?), so I like these pink lace boy shorts (plus-sized version here).

The above are just a few suggestions that I use to make myself feel better. 

How can I help my mom boost her confidence OR how can I stop minding that she doesn’t love herself enough?

You know, my mother has the same problem. I have tried my entire life to tell her that she doesn’t need to be the size she was 20 years ago (she was a size 0 with a brood of children under the age of 10!), and ever since she has ballooned up in weight, she feels terrible about herself.

She can’t extricate size with confidence and always talks about this girl in her class all the boys had liked because she had a 19″ waist and maintained it fiercely as part of her beauty. (Really? Eat something.)

She thinks she isn’t pretty enough or young any more (she is older, but under 150 is young to me), and always wistfully touches my items saying: Wow.. you can still fit into all of your nice things. You look so beautiful.

To get my mother to love herself, has been a painful, uphill battle. I have resigned myself to understanding that she equates beauty with size, and instead, have started complimenting her genuinely on her best qualities.

I tell her she..

  • is really the best mother and grandmother, I send her cards sporadically to thank her (along with cash gifts to buy herself something nice)
  • has an amazing talent for _______ and _______
  • how resourceful she is for _____ and ______ (when I see a specific event)
  • can cook like no other and I miss her comforting meals (I really do)
  • has a kind and generous heart – she’d give you her shirt if she could
  • has a pretty smile
  • has a great personality that is so resilient and happy go lucky that it brightens a room
  • has an amazing sense of colour-mixing and style (she does!)
  • has very beautiful features (high cheekbones which I have inherited)

When something happens that she is proud of, I make sure to make a big deal of it. I tell her how she handled it so well, I marvel at her ingenuity…

Or when she wears a particularly nice outfit, I make sure to make a note of it. If she tries to say it isn’t pretty, I contradict her and insist she looks great because she does and I don’t lie.

You can also try taking her on a shopping spree (or when she needs new clothes or something), pointing out great outfits, styling her and showing her how good she looks.

At some point you may have to also let go.

If she isn’t responding to any of the above because she is too far into her head about her lack of beauty and self-love, she may need sessions in therapy with a good counsellor to help gently tease out the root causes of why she feels like that.

Sometimes you have to understand that you can’t help. Don’t let those bad vibes draw you down. You’re doing your best, and you love her (I hope you tell her that often and genuinely, not just on holidays), and that she’s the best mother ever.

The good news is that you love yourself and haven’t absorbed those lessons, so although we are our harshest critics we are also wrong many times and need to give ourselves a break from trying to fix and help everyone.

I have three different brands- one consulting, one teaching, one product. Do you think I should break them into 3 LLCs, or stay with one LLC and 3 DBAs? Thanks!

I am assuming from your acronyms: LLC = Limited Liability Company, and DBA = Doing Business As …

I am not sure because I don’t actually know what you’re asking as in, for what purpose would you split them? Why are you thinking about this?

Taxes? It would be easier to keep it all as one LLC and have it roll up to one holding with three products. From an administrative point of view, it’s also easier to keep the books and everything centralized.

If it’s for having three separate products that have nothing to do with each other (and you want to cut all associations), or you want to build them individually with separate teams and different brand messages for each, then split them.

Still have a burning question?

You can ask any question using the form here and all of my previous Ask Sherry posts are here.


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