Thinking about gateway boots...

I have no high boots and maybe should keep it that way, but I’m noodling.

I’m exploring the idea of knee-high boots to extend the number of ways I could wear skirts or dresses to work in fall and winter as alternative to the great pants-fit dilemma (still will be majority pants-person in winter). I’m very dependent on skirt-tights formula, and it’s hard to really do colored tights, so while I still think the black-tights/black footwear formula works well for me, it’s limiting. But, I think the dresses and skirts look professional and grown up— I just need to have a high comfort/ease factor with them for my work days.(I did get some gray sweater tights that I think help create interest while still being somewhat monochromatic, and I’m up for some other options, like shades of brown or tweeds or whatever. Also am very up for black+color footwear in the right styles).

My idea is that I might be able to “advance” to outfits of a warmish dress or skirt combo with flat tall boots (meaning 1” stacked, stable heel—possibly 1 ½ “ but no higher).

Here’re the questions for the boot-experienced and the boot-explorers amongst the YLF’ers:

What color boots? My initial thought is I might be most comfortable with some kind of warm brown ,even cognac, and here’s why, but please chime in. My existing fall-mild winter dress options are a black wool pencil skirt ( to be replaced at some point, but with similar), a brownish micro check pencil skirt, and a dark gray “sweater” dress I’ve not worn yet. Actually one more sort of flared skirt I may show later as keep or toss-bought at consignment for this possible imaginary look. So a medium brown would add interest and be different from the black tights look, though it might be more leg-shortening.

I’m really askeert of looking too harsh and a-go-go in black boots. So browns seem friendlier to me, warm and fall-like, kind of the Ralph Lauren look, including with black clothing, say with a brown belt also. However, I will wear either nude hose or some kind of tights WITH the boots, so that’s a dilemma to fit with skirt color + boot color—whereas black boots could use black tights!

Style boots? I don’t wear skinny jeans to tuck in, so I might aim for the best leg-fit and refinement for skirts, and not for tucking.

Outfits? Do pencil skirts work, or would I need to aim for more fit-and-flare looks for boots? Do skirts need to be the longer bottom of knee length?

Another issue is that I have no idea whether or if I’ll ever find more dress options to go with boots—I’m pretty hard to fit and would need warm fabrications. So it’s a mystery as to what direction things might go, color-wise, but would be fall-winter colors, at least. I guess if things went really well I could justify black and brown eventually.

So, how did you get started in boots? Will it be more that the fit and style will drive it and the color will fall where it may?

11 years ago

cinnamon fern

Veteran

Oooh, tall boots + skirt/dress is my favorite winter work uniform! I will try to answer some questions.

Color: cognac works with black, grey, and brown, so would maybe be easiest for you. I usually wear nude tights or bare legs with my cognac boots. I don't worry too much about leg-shortening because all my boots have heels, and on me skirts are way more leg-lengthening than pants anyway.

What about burdundy/oxblood? This might be harder to find though.

Style: something sleek. Maybe a low wedge? I like these, although they are not in my budget:

http://piperlime.gap.com/brows.....=882035002

Outfits: pencil skirts definitely work with tall boots. How much skin you want showing between boots and skirt probably depends on the shape and proportions of your legs. For me, high on the kneecap works the best.

unfrumped

cinnamon fern, thank you so much for boot-thoughts! I could probably do a low wedge. The link is sleek! But pricey for gateway !
I think I'll at some point just go exploring--even DSW just because it's easy tor roam around and try things on with no SA pressure--and wear a skirt of some kind when I go.

TraceyLiz65

(website)

I agree that Cognac would be a great starter boot and would work with all the colors you describe. Just wanted to wish you luck in your journey to find the right ones!

Glory

I also think that Cognac would be great. Perhaps something like these ones from Aldo. I tried them on last year and was so very tempted.

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Anonymous

I loooove cognac with fall/winter clothing and it's surprisingly versatile. I also like Cinnamon's idea of burgundy/oxblood, though they're harder to come by.

Firecracker (Sharan)

unfrumped, I encourage your foray into boots. They are such a great option to have, in my opinion.
How I got into boots: After years of living in warmer climates (and developing quite a sandal wardrobe!), I moved to Seattle. I've always liked the looks of boots, and now I had the weather to wear them. I think about the same time, more boots with a wider calf became available, so I was actually able to fit some of them on my legs.
I would look for a sleek fit, especially at the ankle, because it's easy to transition into a boot that way. It's very flattering to the leg and less different than the tights-and-shoes look that you are comfortable with. That's where I started. With subsequent pairs, I branched out to other styles, but come to think of it, all of my tall boots do nip in at the ankle, even if they are roomy enough to wear over skinny jeans.
You might try bookending with your hair for your first pair. If they go with your hair, they'll go with most things in your closet. That idea would suggest a dark brown or black--yes?
You can wear any length and silhouette of skirt with tall boots, especially those with a little bit of a heel and not the very flat riding boot look. Knees can show these days. Angie has a post or two on this. I'll try to hunt them up.

ETA: here's a post from Angie that gathers a lot of blog entries on skirt lengths with boots (see partway down this post): http://youlookfab.com/2013/03/.....th-skirts/

Tracey, Glory, and Stacey--thanks for the enabling?

Firecracker--you hit the nail when you described a fitted ankle look--I would likely not want to start with rugged clumpy or "big" boots. Thank you for the link back to Angie's post--I actually love the over-the-knee flared skirt--the riding skirt look--didn't know if it's too 80's or whatever, or what would modernize it. That length has some appeal because then I don't have to worry about the pantyhose or tights police in what matches or does not or how much skin or whatever. Plus it's an issue when you sit down--no matter what, pencil skirts always show more leg when sitting, whereas the flared drapey skirt is just the opposite. My sweatery dress --not really sweater but a soft knit--has sort of that look in the skirt, though is not fully over the knee.

lyn*

My favorite boots are the "Vanna" model (Doc Martens) - I got them in a roan red and wore out the soles so bad I'm still embaressed to go to the cobbler to ask if he can fix them up! I wear brown > black, but whatever colour you decide on, it does depend on the rest of your clothes.

Makrame

My first boots were flat brown water-resistant Timberland boots, at a reasonable price (less than $100). They are not too rugged but fairly practical, and fit well around the calves (no gaping). I still wear them.

My next pair were tall black boots with a wedge heel but it tooks me almost two years to start wearing them - they just felt like "too much" for me - too dressy? too shiny? Not sure. Now I wear them all the time.

I definitely wear a lot of skirts/tights/boots in the winter, more so than pants, and I am in the snow belt. So I wholeheartedly support the idea of boots for fall/winter.

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