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10 Secrets to Styling Any Outfit Perfectly

I use these exact 10 rules unconsciously (or consciously?) when I want to do something different with an outfit that I love to wear, but maybe want to twist or change a little for the day.

I thought I’d share them all with you!

Buy one size bigger

So this rule applies in two instances; the first being a fitted dress or outfit:

If a dress fits and skims PERFECTLY, I take a size bigger. I want it to not be skintight, or for myself to not be able to feel comfortable bending over, sitting down, or even going to the washroom in it.

The second time this rule applies is when you want something to have that classic slouchy look. Sometimes a fitted t-shirt is great, but a slightly slouchy one is better especially paired over skinny jeans or leggings.

One size up, can give you that perfect “I just threw this on” messy, casual drape without being too contrived & perfect.

Like with this Dior sweater I knew was a size too large for me:

Get it tailored

When you buy one size up, you MAY need to nip it in the sides to bring it in a bit for your shape.


Nevertheless, I take in pretty much everything I own to be tailored. Nothing fits me perfectly off the rack, believe it or not. Either the straps are too long (ALWAYS! I hate plunging necklines), or the hems are too long (grr to not being 5’7″) or I want that slouchy boxy top to be just a little nipped in.

I bought this dress in a US8 and had it tailored down:

If you hate the way it looks on you but you like everything else about it..

TAILOR. TAILOR. TAILOR.

Mix the highs and the lows

The two ways I use this rule is to either mix high-end brands with low-end stuff (usually boots, bags and coats are great high-end pieces that will elevate any outfit you have own), or it is to think about the hemlines and volume of each piece.

If you have a high hemline, wear lower heels or flats with them to avoid looking trashy.

If you have a long hemline, wear something heeled with them for something different, or knee-high boots.

This is a great example: I have a low-end outfit (random skirt & cheap sweater) paired with luxe suede booties. The hemline is high so the booties have a low heel to compensate for it rather than wearing them with high heels:

For the volume of pieces, if you wear something tight on top, make it loose and slouchy on the bottom and vice versa.

Casual & dressy / Tight & Loose

I LOVE mixing up dressy things like a tweed blazer with a more casual pieces like jeans and a t-shirt.

Or like in this version with pearls:

Or like this, a casual safari shirt with a fancier pleated ballgown-like midi skirt:

You simply can’t go wrong with doing this great juxtaposition of styles to really make you tilt your head.

Other great combinations include a gown with a sweater over it, à la Jenna Lyons for instance; a casual sweater with a dressy gown from the Met Ball or Sharon Stone when she wore a Gap t-shirt over a ballgown skirt at the Oscars.

mix-dressy-and-casual-style-rule

Mix fabrics & prints

Along the same lines of mixing high and low, think about the FABRICS being mixed too.

Classic fabric combinations to me:

  • Tweed and Silk
  • Leather and Lace
  • Denim and Linen


Classic print combinations to me:

  • Stripes and Florals
  • Stripes with Stripes (vary them!)
  • Dots and Stripes
  • Dots and Florals
  • Any black and white prints mixed with each other
  • Plaid and Leopard
  • Gingham / Checks and Dots

Here are some examples:

You can also mix colours if they’re in the same family and play with those geometric shapes:

A photo posted by Sherry @ Save. Spend. Splurge. (@saverspender) on


Buy Mens or boys clothing

The larger sizes of the men’s clothing work really well especially if you roll up the sleeves and wear it as a slouchy alternative to a fitted one.

Or you can use it to turn it into a DIY skirt like I did below:

Think: boyfriend jeans, tweed professor jackets, large buttoned up shirts.

Boy’s clothing is great when you want something cool and fitted. Little boy’s blazers have shorter sleeves and fit a woman’s body quite well. You could end up with 3/4 sleeves, or something more miniature-sized.

Layer, tuck, roll or cuff!

Do the half tuck in front, tuck it all the way in, layer different shirts on top of each other, or roll up the sleeves & the jeans.

For instance, you can layer sweaters over dresses and belt it to bring it all together:

And here’s another example of a casual shirt layered over a dress and belted:

Play around with the dimensions of the pants, sweaters, tops & jackets by changing them!

I came up with this idea recently of layering DRESSES I had on top of each other:

I kind of like the look, it looked like a Vietnamese ao dai.

I used to be such a hater on cuffing jeans because I thought it would make me look short but it looks great over some ankle boots for a casual Sienna Miller boho kind of look.

You can do a roll cuff, a thicker cuff, a thinner cuff on your jeans and pair it with heels!

Or how about layering jackets? Wear a blazer underneath a leather jacket to give the outfit more dimension.

Belt it

When in doubt, belt.

My own instagram shows this.

I LOVE belting my tops, but I don’t stop there, I like belting my sweaters, my blazers, my jackets… anything to give my waist a little definition.



here’s a light silk wrap chiffon coverup I belted:

I also don’t just use belts to belt my clothing, this is a silk scarf I used as a belt:

Don’t match everything exactly

Tan leopard on leopard? No, please. We are not Peg Bundy from the 90s.

Don’t dress in one colour head to toe unless you are making a sartorial point of doing so, otherwise you’ll just look like a big stick of celery.. or a carrot.. or a lemon.. you know, some kind of fruit or vegetable.

Matching works in the sense that you can wear various shades of blue together to make something interesting out of an outfit, but not when the shades match PERFECTLY.

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Sherry of Save. Spend. Splurge.

Millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using TheBudgetingTool.com. Since then, I have paid my $600K home in cash (my half was $300K), my $180K casr in cash, worked 50% of my career (taking 1-2 year breaks), and quadrupled my income within 2 years of graduating, going from $65K to $260K with an average lifetime savings rate of 50%. I could retire today if I wanted, but love my work-life balance as a freelancing consultant in STEM (Science, Technology, Engineering, Math). I am all about balance - between time and money, and also enjoying my money. I also post daily on Instagram @saverspender.

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2 Comments

  1. Elisa

    Thank you for this post. Awesome and very helpful information. You have great taste!

    Reply
    1. save. spend. splurge.

      Thank you & you’re welcome

      Reply

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