Fashion police — help!

I went on a bit of a bender after Christmas. A shopping bender. A clothes-shopping bender. It felt sooooo good! Not only were there amazing deals to be had (I didn’t pay more than 50% of ticket price on anything) but I was shopping for a size I haven’t worn since before any of the babies were born. I’m down more than 25 lbs since August, and down more than two jean sizes! Every time I tried on a pair of pants, I did it with trepidation, expecting to find a size 12 way too tight — and in some cases, I even found it was too loose. Yay me!!

I took full advantage of the Boxing Day sales, and in three quick trips spent about $275 on new clothes, but with deals like $19.99 for a $78 pair of Gap tuxedo pants, and $11 for a $65 Jones New York skirt, I’m sure I ended up with about $600 worth of clothes.

After more than two years of buying clothes based on a sole criterion (does it fit enough to keep me decent?) it was pure bliss to be buying things because they were pretty, or funky, or just felt really good. And buying actual outfits instead of trying to make random impulse purchases fit with what I already own. I ended up with three skirts, four pairs of pants, a blazer, a couple of blouses and sweaters and even a pair of kicky little ankle boots. I tell you, it was like living my own personal episode of What Not to Wear!!

The problem, of course, is that I didn’t have Stacey and Clinton to right my fashion wrongs. I *think* I did okay, but there are some fashion questions that continue to escape me. Perhaps you, the wise and wonderful bloggy peeps, can help?

For example, the kicky little ankle boots: can I wear them with a skirt? I have both a narrow little skirt that falls to a bit above my knee and a fuller skirt with a flare that falls just to the knee. Can I wear the short boots with that, or do I need calf-high boots for that?

And since I’ve got your attention, what about jewelery? If I’m wearing gold-tone earrings, do I have to wear a gold-tone in my necklace and/or bracelet? And is earrings plus a necklace plus a bracelet too much? Oy, I’m so bad at this!

And what about makeup? Am I supposed to match my eye shadow colour to what I’m wearing, or can I wear the same purple-to-grey cool palate with warmer oranges and browns?

Ugh, you can see I need some serious intervention! I’m actually excited about going back to work, just so I can wear my fancy new duds, but I don’t want to look too much like a fashion “don’t” as I step outside my comfort zone!

Author: DaniGirl

Canadian. storyteller, photographer, mom to 3. Professional dilettante.

16 thoughts on “Fashion police — help!”

  1. I am by no means a fashionista or a contender for a host of What Not to Wear, but here is what I have observed in others and had in advice:

    Ankle boots – they just don’t look great with short skirts – they make legs look stumpier instead of longer. They look awesome with pants though – nice fitted jeans or really nice fitted dress pants. Great.

    Jewelery – I used to go with silver with silver, gold with gold but not anymore. Ever since the emergence of white gold, I mix it all up and I think it looks really nice.

    Makeup – not an expert here at all but I recently had advice from the great people at Saphora. Wear eyeshadow that highlights your eyes not your clothes. Don’t try to match make-up to clothes. Just match it to your skin type, eye colour, skin colour etc.

    Hope that helps, fwiw!

  2. I’m pretty sure you can wear those “shbooties” (little ankle boots) with just about anything these days – i’ve seen a lot with skirts and opaque tights.

    Also with jewelery, i think you should either go gold (yellow) or white (or silver) all the way

    sorry – can’t help with the makeup ’cause i rarely wear it myself!

  3. This is hard. I don’t wear makeup or jewelry at all. Too lazy for the former and too slouchy for the latter. As for kicky ankle boots, I’m afraid Ortho Girl is outta her league commenting. My gut reaction would be “no”, after watching too many years of undergrads strolling through the library in short skirts and Ugg boots, but, then again, who knows what the cool kids are doing these days?

  4. omg, i could not confidently answer even one of your questions. but i could tell you which hoodie looks best with a pair of jeans.

  5. Boots: No way – they need to be higher
    Jewelery: tones need to match but not the actual jewelery – as for how much – depends on the outfit and how simple it is and/or how big the jewelery is.
    Makeup: Not my thing and when I have to wear it – I call my sister

  6. I’m with Virtually There about the eye shadow – I always wear a mauvey tint, and all the make-up advice I’ve ever seen has been dictated by eye colour, not outfit. I think matching your eyeshadow to your clothes was something we bade farewell to on New Year’s Eve, 1989.

  7. Okay. I know the answer to this one. The ankle boots are more than acceptable with any skirts, and would likely look good with the pencil skirt. But….that is on the fashion models. I have boots very similar, and I’m sorry, but to me, it doesn’t work. So put it all on, take a look, and ask yourself, “Am I rocking this, or am I a bit self-conscious about this?”…then make your proper choice from there. Re: Jewelry – mixing metals is totally fine these days (as is mixing eras, or anything really). Re: makeup….no no no NO to matchy matchy. Like Virtually There says, you want to wear what looks great against your eyes. Once you get to work, come get me – I used to work as head of wardrobe for film and tv shoots – I love to dress people…!

  8. What I’ve learned from many hours of watching What Not To Wear (that makes me an expert, right. ;-)) Short boots with short skirt, acceptable, but Pamela has it right. Works well if you have twigs for legs. Jewellery just needs to “go” together, not neccessarily match. Matchy matchy is bad. That goes for shoes and bags too. no need to match those any more either. Make up, go to Saphora. They will totally guide you in the right direction, and it is what highlights your features and not your clothes!

  9. Hooray! Hooray Dani!
    You did awesome with your diet and now you get to enjoy your new outfits, your new you. Yes, go get your make-up done at Sephora and you’ll be set there. Put on jewellery that makes you feel good and leave those ankle boots for pants, imho.

    But now listen to me girl. This part is important. take all you pre-diet clothes and DITCH them. ALL of them. No more bulky sweaters and old large comfy pants. It’ll make gaining weight and slipping back into old habits too easy.

    mwah

  10. my personal opinion about short boots and skirts – i hate that look – like one commentor said – it makes your legs looks stumpy. instead, wear them with pants. and get yourself a pair of high boots for skirts. i’m sure you can get a great deal on high boots right now.

    makeup – totally doesn’t need to match your outfit.

    jewellery – they say you can mix and match silver and gold but i still make sure my earrings and necklace “go” – but what is great is some jewellery pieces have both gold and silver in them so they really will go with anything.

  11. How about no jewelry, no make up and no baby spit up on the clothes. That seems like a standard that is attainable by a mother of three young boys!

  12. Congrats… Alot of work to get there but I can see you feel AWESOME and when I saw you last you looked awesome!

    I’m no fashion plate but NEVER wear short boots with a Short Skirt. NOW If you had a slong skirt to the ankle you can. MY rule of thumb.
    Long boots look so much nicer and sexier with a short skirt. NOW you have to get the perfect pair of Pumps.

    Jewerly…I mix it up but I’m funky that way. I’m not the matchy matchy type…as long as there is some of both in different places.
    I wear two braclets in silver and gold and then put on gold earrings and a silver necklace. I may look goofy but whatever… I sure someone somewhere in acient times did it. I’m just the through back.

    Kudos to you for loosing it. I still trying and I am down 15 but I have tons more to go. I think it helps that I am out and away from my cupboard and taking the stairs at school, not the elevator.

  13. Try to avoid wearing gold jewelry altogether…if you have to wear it, embrace it and wear ONLY gold…please do NOT mix it with silver, white gold or platnum! A necklace, earrings and bracelet is overkill. Less is better. Wear one great piece of jewelry (beside your wedding band and engagement ring, of course). And since you’ll be back at work, don’t forget the ease and sophistication of a simple strand of pearls or tiny diamond studs.

    For you (I get the impression that you are tall and curvy, lucky gal!), the ankle boots would look best with layered, longer outfits and opague tights…never with a short skirt.

    When you do wear short skirts to show off your legs, make sure to wear great tights and consider flats as opposed to knee-high boots.

    Remember that long cardigan-type/belted sweaters are in this winter, and look great when worn with jeans, pants, skirts or simple dresses…great bang for the buck since they are so versatile. And WARM in this awful Ottawa winter!

    Makeup should not necessarily match the outfit…your safest bet is earthy eye makeup. If you want to make a statement or find a hue that complements the clothes, do it with your lip colour.

    Enjoy your new wardrobe and hard-won weight loss…you’ve earned it!!! Sounds like you’ll be the best-dressed gal in the office.

  14. Oh Dani, you know this is the kind of post I like!

    Ankle boots and skirts are very in right now, but I agree with the bloggy peeps: not flattering, since they kind of cut off your legs, and make you look stumpy. And I’ve seen your legs. They’re nice, so please don’t do that to them.

    Jewelry: mix it all up and have fun, but you don’t want to look like a Christmas tree, right? Besides, don’t you find that you immediately take off bracelets when you sit at the computer…then lose them?

    Lastly, eye makeup. Melanie Love would shoot me for this, but I say NEVER match it with your outfit. You’re not 13 and you should know better than to wear anything but what looks best on you just so it matches your outfit. Also, your purply stuff looks fantastic, so it would be a pity not to use it.

    Can’t wait to have you back!

    Also, my Captcha is “deserved large”. Means you can treat yourself to an ice cream cone, no? 😉

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