The first thing that always comes to mind whenever I think about fall fashion is boots: whether tall or short, suede or leather, there’s no better choice of footwear to complete any fall or winter outfit. If you’re like me and prefer to invest in styles which will last for years, shopping can get overwhelming with thousands of pairs to choose from: this is why I decided to create a post that can help you narrow down the must-have styles for every wardrobe! I’m breaking this post into two parts: tall boots and ankle boots, with different categories for each section and style tips, as well as where to buy them. I hope you will find this information helpful for building your own timeless boot collection!
Must-Have Tall Boots: High Heel, Over-the-Knee, Riding & Rain
The must-have tall boots for every wardrobe:
- High Heel
- Over-the-Knee
- Riding
- Rain
High Heel
A knee high, heeled black boot is a classic that will just never go out of style, period. I’ve had this pair for about three years now and love them as much today as when I purchased them. The modest heel elevates any outfit to give it a dressier feel–treat them like the elegant sister of your black riding boots.
Style with:
- dresses
- knee-length skirts
- midi skirts
- leggings/skinny jeans
Featured boot:
Stuart Weitzman ‘Park’ (old; similar)
Over-the-Knee
Although they may not be considered a true classic yet, over-the-knee boots definitely appear to be sticking around. The particular style I am wearing has been offered for years, and I finally pulled the trigger on this black suede pair last year. I never expected I would wear them as much as I did, but I found myself pairing them with everything, especially the shorter skirts and dresses in my closet. Bonus: the additional length makes them a warmer choice for winter!
Style with:
- mini skirts
- short dresses (i.e. shift and trapeze styles)
- leggings/skinny denim
- leather pants
- ponchos/capes (they help create a sleek lower half by balancing proportions)
Featured boot:
Stuart Weitzman ‘Highland’ (available here and here)
Riding
The riding boot is absolutely the most timeless of all boots, which is why I always invest in the best I can afford. Every woman needs a black and brown pair, but I also think gray is a great neutral color to own. Frye is my favorite brand for riding boots (which you can probably tell if you’ve been following me for awhile!) because they are the best at making authentic equestrian styles with beautiful leathers. I typically buy one or two new pairs of Fryes each year, and although I’ve had some of mine for over five years, they are all in great shape. **A tip for extending the life of your boots: take them to a cobbler to have rubber soles made–it is very inexpensive and worth the trip. Many riding boots have leather soles, and doing this will prevent them from wearing out quickly; plus, the rubber is more shock-absorbing and comfortable for walking.
Style with:
- leggings/skinny jeans
- distressed denim
- shirtdresses (think chambray or plaid)
Featured boots left to right:
- Frye ‘Mustang’
- Frye ‘Jane Tall’
- Frye ‘Melissa Tab Tall’ (available here and here)
Rain
If you don’t already own a pair of rain boots, go buy some now and thank me later! Rain or snow, you’ll need them all year round (when it’s cold, I like to add fleece socks). Hunter, the renowned British brand, is my favorite because they are the most flattering and come in a wide range of styles and colors–and you can’t go wrong with a company that’s been making boots since 1856! **Tip: to keep your boots looking glossy, vigorously rub them with a clean towel before applying boot shine.
Style with:
- everything: they are meant to be functional!
Featured boot:
Hunter ‘Original Tall Gloss’ (in black and other colors here; violet no longer available)
Must-Have Ankle Boots: Leather, Suede, Statement & All-Weather
The must-have ankle booties for every wardrobe:
- leather
- suede
- statement
- all-weather
Leather
Leather ankle boots in black and tan are a no-brainer since they will go with everything you own. Booties are a great transitional footwear choice for late summer and early fall, when it’s not cold outside (I usually wear mine all the way into December). **Tip: wear them with no-show socks such as this; they are thin and feel much better than regular socks–plus you won’t see them peeking out of your shoes!
Style with:
- cuffed jeans
- denim shorts
- leather pants
- legging jeans
- short dresses
- knee-length skirts
- midi skirts
Featured boot:
- Frye ‘Reina’ camel bootie
- Dolce Vita black booties (old; similar here and here)
Suede
Suede ankle boots are much like leather in terms of styling, but the texture definitely has more autumnal appeal. It’s good to have one dressy black pair and a casual tan style, and as I mentioned with the leather ankle boots, I wear mine with no-show socks (unless it is cold, in which case I’ll opt for tights).
Style with:
- leather pants
- legging jeans
- short dresses
- knee-length skirts
- midi skirts
Featured boots:
Statement
Once you’ve built your must-have boot collection, it’s always fun to throw in a statement pair or two, like these fringe and studded styles. Treat them like your other ankle boots, but be careful not to overdo it with the rest of your outfit, since the overall effect can be too busy (especially when it comes to fringe).
Style with:
- cuffed denim
- leather pants
- legging jeans
- short dresses
- knee-length skirts
- midi skirts
Featured boots:
All-Weather
For cold, wet weather, nothing beats a pair of insulated all-weather boots. I recently added this pair to my collection and they were perfect for hiking around Germany, not to mention they’re actually kinda cute! (See how I wore them here).
Style with:
- everything–like rain boots, they are meant to be functional!
Featured boot:
Aigle; similar
Favorite Places to Shop for Boots:
