Outfit Formula: Dresses with Taller Boots

Taller boots are trending, and can pack quite the visual punch. They are insulating too. If you have a pair that you like but aren’t wearing, dust them off and wear them with dresses. 

Here are ways to wear dresses with tall boots as the weather cools.

1. Summer Dress with Taller Boots

This is dead easy. Pair a summery dress with a pair of tall boots. Add a bag that works with the palette of the outfit, and Bob’s your uncle. Here, a shorter dress with a boho vibe is combined with toffee cowboy boots. A tan bag is a tonal match to the boots. A casual necklace on black cord completes the look and fills the gap created by the low neckline.

Summer Dress with Taller Boots

Here are examples of adding taller boots to longer dresses that you typically might wear in the Spring and Summer. The boots are not cowboy boots. A simple way to move dresses into transitional weather, as long as you have the boots.

2. Dresses with Stompy Black Boots

Here’s a version with an on-trend ‘90s flavour. Dresses can be solid or patterned and any length. They are usually made of soft fabric and have black in the patterns to match the boots. Stompy boots are generally black, relatively flat, casual, and chunky. Boot heights tend to be mid-calf, but shorter and taller boots work well too. This version adds a black bag to match the boots, and a canary yellow coat to complement the ochre in the pattern.

Dresses with Stompy Black Boots

Here are more ways to wear dresses with stompy boots. Black bags match the black boots. Sometimes they match a black topper. Where there is no black in the outfit, black boots match the black hair of the model.

COS
Puff-sleeve Midi Dress
View Info
Top Pick
2
COS
Pleated Shirt Dress
View Info
Top Pick
4
COS
Belted Shirt Dress
View Info
Top Pick
4
COS
Pleated Shirt Dress
View Info
Top Pick
2

3. Transitional Dresses with Taller Boots

This is an example of a warmer dress that you can wear with tall boots. It’s typically thicker, longer and has sleeves.The navy dress here is combined with brown boots and a belt to match, which is nice with the model’s brown hair. A cream coat adds a crisp and pretty touch. I vote a bag that matches the palette, or throw in an unexpected pastel or bright.

Transitional Dresses with Taller Boots

Here are a few more examples of warmer dresses with tall boots. The dresses are midi and midaxi length, and the boots are quite dressy. Bags do not need to match the boots. You might be warm enough wearing this look in Winter, especially indoors.

Shopbop
MISA Charlotte Dress
View Info
Top Pick
4

4. Short Dresses with Taller Boots

Last, if you prefer dresses with shorter hemlines, here are ways to wear those. Hems range from mid-thigh to just above the knee. These silhouettes are waist-defining, but feel free to surrender the waist. Boxy and voluminous cuts look great with tall boots.

Now that I have a pair of gorgeously tailored knee-high boots, you can bet your bottom dollar I’ll be wearing them with some of my midi and midaxi dresses. I love how I can extend the wear of some of dresses in this way. Can’t wait!

Trend: Brown is Back

Red is the colour of the season, but brown is the next big on-trend colour for Autumn and Winter ’23 and ’24. The earthy neutral fringe trended for a while, but has finally gained momentum and is back to having a mainstream fashion moment after a fifteen year hiatus. 

Brown is popping up in clothing, footwear and accessories. Simply described as brown, or as one of the many variations, including dark chocolate, milk chocolate, espresso, mahogany, hickory, clove, truffle, chestnut, birch, beech, mocha, java, saddle, and fudge. Some browns are very dark and almost black. Others are lighter, but still a dark neutral. Browns can be on the warmer or cooler side. Available mostly in solids, but also in some patterns. Take your pick.

Shopbop
STAND Grayson Pants
View Info
Top Pick
4
Shopbop
STAND Trek Blazer
View Info
Top Pick
2
Shopbop
A.L.C. Andie Dress
View Info
Top Pick
1
Shopbop
AG Farrah Boot Jeans
View Info
Top Pick
3
Shopbop
Harlyn Silk Camisole
View Info
Top Pick
1
Shopbop
Theory CL Kick Pants
View Info
Top Pick
3
Shopbop
STAND Delphine Dress
View Info
Top Pick
2
Mango
Cable-knit Cardigan
View Info
Top Pick
2
Mango
Satin Print Shirt
View Info
Top Pick
2
Mango
Striped Rib Sweater
View Info
Top Pick
2
Mango
Leather-effect Jacket
View Info
Top Pick
1
H&M
Bag
View Info
Top Pick
2
H&M
V-neck Bodysuit
View Info
Top Pick
1
H&M
Double-breasted Jacket
View Info
Top Pick
1
H&M
Biker Jacket
View Info
Top Pick
1
H&M
Wool-blend Coat
View Info
Top Pick
2
Mango
Leather Midi-skirt
View Info
Top Pick
2
Aritzia
TNA cozy crew sock
View Info
Top Pick
3
Aritzia
Babaton conan pant
View Info
Top Pick
3

Brown has a strong ‘70s connotation for me. As a child of the ‘70s, I vividly remember people wearing brown. My late Mama wore a lot of brown with mustard, teal, burgundy, toffee, light blue, and antique pink. It is indeed a very versatile dark neutral. Maybe more versatile than charcoal, black and navy. To my eye, brown looks great with other dark neutrals, light neutrals, earth tones, jewel tones, pastels, brights, mid-tones, muddy colours, neon, and metallics. That covers ever colour in the universe.

I wore a bit of brown in the ‘70s, and under duress in the ‘80s in the form of a brown school uniform. The latter killed brown for me for decades. It was only in July this year that my mood swung in favour of wearing it. I’ve recovered. I saw a Theory pants suit I fancied, held it up to my new dark blonde hair, looked in the mirror and thought, I like it! The brown works well with the brights, light blue, and cream in my wardrobe. One of my wild cards of the year, and I’m enjoying it a lot. I love a spontaneous purchase that works out. Quite the thrill.

Currently I have four brown items in my wardrobe. The pants suit, which I’m wearing here. A patterned mesh top to go with it, and an old pair of tortoiseshell RayBan sunnies. I don’t plan on getting more brown items, but never say never.

Some of my clients are thrilled with the return of brown, while others are less interested. How about you? Does brown feature in your style?

Black Is Not Universally Flattering

Solid black wardrobe items are spectacular when you wear the colour well. Chic, dressy, streamlined, strong, hard-edged, and dramatic. But it can also look harsh, flat, draining and overwhelming. Black is not a universally flattering colour. 

Beware of Black

Tame black by wearing it as a pattern, as bottoms, with another strong solid, or as outfit accents. Soften black by showcasing skin. Break up its expanse with texture. Make it sparkle with accessories. Wear stronger make-up to match its drama.

Sometimes wearing solid black is dead right. It allows you to blend in when you don’t want to stand out. It can be practical, versatile, dramatic and easy. But if black isn’t for you, complement your style with another dark neutral, like navy, chocolate, or charcoal.

Roundups

Simpler Items

This week's list of top picks list is about basic pieces.

Read More

Assorted Items

Items for Summer, both in and out of air conditioning.

Read More

Casual Summer Vibes

This week's top picks are good for a casual Summer vibe.

Read More

Summery Earth Tones

These items are for those who like to wear casual earth tones in warm and hot weather.

Read More

Hints of Spring

Some tried-and-tested winning items to refresh your style for Spring.

Read More

Dressier Items

An assortment of dressier top picks might be just what the doctor ordered.

Read More

My Whiskey Complement

I got a pair of whiskey knee-high boots at this year’s Nordstrom Anniversary Sale. I mentioned at the time that I wanted to get a bag to match and complement them, and since then I’ve bought one for a song that’s a beautiful tonal match. Of course, I won’t always wear them together, but now I have the option when I’m in the mood for matching.

Whiskey Complement

It turns out that my old toffee pieces like a thirteen-year-old Burberry scarf, a ten-year-old cashmere wrap, a seventeen-year-old studded belt, an eight-year-old short puffer, and a one-year-old pleather moto jacket work well with the new boots and bag. Most of these items aren’t a perfect colour match, but they create outfit cohesion and look great when worn together nonetheless.

I find it tremendously satisfying when old wardrobe items work well with new ones. It makes it easier to create outfits that look pulled together, and refreshes the way I wear old items. In some cases, it makes me fall back in love with old items that I haven’t worn for a while.

When my items relate to each other in some way, I definitely get better use out of them and have them in my wardrobe for longer.

Buying Items on Final Sale

Here in the US, buying wardrobe items on final sale usually means that you get them at a deep discount, but you can’t return the item if it doesn’t work out. An exchange or store credit is typically not offered either.

Buying items on final sale is particularly risky when you buy them online and haven’t seen them and tried them on. Even more so if you are unfamiliar with the brand’s usual fit and quality. Colours are often misleading in the online pictures. I vote avoid buying items final sale in these instances, unless you’re prepared to resell or pass them on. 

Final sale is a better bet in stores when you’re able to see, feel, and try on the item. You can be quite confident you won’t need to return the item. The same goes for online items when you’re familiar with them and know how the brand works for you. Or have bought the same items in the past.

On a couple of occasions I have neglected to read the fine print when buying a heavily discounted item online, only to find out they were final sale when I tried to return them. I appreciate it when online retailers put in bold red writing that the item is FINAL SALE before you hit the purchase button. Lesson learned. I must be extra careful to read return policies when purchasing heavily discounted items online.

The items were a Jason Wu skirt from The Real Real, and a handbag from Furla’s online store. First prize would have been to return them, since neither was the right fit. Since I didn’t have that option, I had the skirt altered to fit. Not perfect, but greatly improved. The bag is a tad small for my purposes because it can’t accommodate my second pair of specs. I use it when I don’t think I’ll need the second pair, which are progressives that I wear when reading.

On the other hand, I have had many final sale successes. I recently purchased two pretty and versatile cotton pointelle tops on deep discount and final sale from Boden. I know the brand, fit, and quality well, and have a lot of Boden knitwear in my wardrobe. I was very confident they would work. Boden also kindly warned me that the items were on final sale as I added them to my shopping cart. I ordered the green first. It was perfect! I ordered the navy stripe afterwards. Just as fab.