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How to Wear: Winter Boots

January 21, 2012

Daily Digest

How to Wear: Winter Boots

Pictured centre Church’s riding boots

My favourite part of my winter wardrobe  is fishing out my winter boots again. However, every year it gets more and more confusing, as trends tell you that buckle boots are in one month and ankle boots the next, even so far as the over the knee boot trend, also referred to as OTK boots.

Trends aside, here are our tips to guide you through boot wearing every winter.

Boots and jeans

To-the-knee boots, or knee highs as they are often referred to, are a style that suit most people and can be worn to the office or on your downtime at the weekend. If you love the Parisian look and long to wear skinny jeans with boots, you should choose a pair of slim cut or skinny jeans in the same colour as your boots.

When buying your boots, be sure to try them on with the jeans that you have in mind to see if they fit into the boots. Leggings or jeggings are in abundance this year and make a less bulky option, sure to fit into your boots.

Take heed from Gossip Girl’s Blake Lively and Trinny Woodhall (both pictured) who both avoid a light colour worn with dark boots (or vice versa) as it “chops up” the line of your leg, making you look shorter than usual!

Also, do not wear jeans over flat boots; this is a look saved for boots with a heel.

Flat boots

Again, for flat boots, wear your skinny jeans or leggings tucked inside your boots. If you’re lucky enough to be a tall gal, then you can wear any colour jeans with your boots.

For shorter, curvier ladies, stick to a dark wash denim such as black or indigo blue. If, like me, you fear that tucking your jeans into your boots will make you look even shorter, then wear a longer top which will give the illusion of a longer torso.

Boots under jeans

A riding boot style is a classic “to the knee” boot that will do you for years and comes in various heel heights, so suits both the high heel and flat heeled fans. They look good with jeans tucked in, as well as under jeans. Pictured centre is the classiest of all riding boot brands by Church’s (€630 from Net-a-porter) or at the Church’s outlet at Kildare Village (Phone: 045 527050). You’ll also find good leather riding boots in Rockport, a boot I’m a big fan of.

For wearing your boots under your jeans, I recommend opting for a round toe and a sturdy heel, as a pointed toe with a stiletto heel can look a bit like you’re the wicked witch of the west, which obviously, is not a good look!

Boots with dresses and skirts

Another thing about to-the-knee winter boots, is the fact that you can also wear them with dresses and skirts. This is a look that’s become more and more acceptable as office wear (instead of court shoes), preferably if you wear them with opaque tights. Try and choose tights in a colour that’s in unison with your boots, as wearing boots barelegged with dresses or skirts can look a tad tarty.

Bare legs with boots

If you do have great legs and want to show them off when the weather permits, avoid a boot style with a sky scraper heel and pick a colour close to your skin tone – nude or beige coloured footwear will elongate the line of your legs.

Also, make sure your top half is conservatively dressed, for example wear a high neckline and/or long sleeves.

If you are short and want to wear a dress or skirt and boots, you should wear a miniskirt with dark, opaque tights and dark boots – here it’s a case of the monochrome colour having a leg lengthening effect

For the big chill

Inevitablly, when snow or harsh wearther hits, people rush out and buy appropriate footwear. Make sure your choice is waterproof and if possibly, cosy too. Our top choices are Sorel for snow boots (available at the Great Outdoors,53 Degrees North, Fitztpatricks and Tres Chic) and EMU for cosiness (EMU’s are also 100% waterproof and cheaper than UGGS).



It’s basically all about proportion and as much as the boys might like it, you really don’t want to show off more bare leg than skirt.

Have large or small calves and can’t get boots to fit you? Read our Ask the Stylist tips on the perfect boots for you.

Related posts:

  1. What She Wears: Autumn Winter Boots
  2. Ask the Stylist: Wedge Boots
  3. Accessory Alert: Rockport
  4. Winter Wardrobe Essentials
  5. Ask the Stylist: Boots for Large Calves
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3 Responses to “How to Wear: Winter Boots”

  1. JADE Says:

    it is so oboevious the only way to wear the winter boots is tucked in to the trousers cause any other way does not look good ……….. well in my view ………………………….. cu!!!!!!!!!!!!!!!!!!!!

  2. Nora Says:

    love the tips you give really need good winter boots, I think you can do a lot with boots not only with the trousers tucked in , I think it depands on your height and cut of style you wear.


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