Still feeling odd about tucking into boots. - YouLookFab Forum

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Outfits Ensembles Trends Advice

Still feeling odd about tucking into boots.

Cilleena

Veteran

I know this look is pretty mainstream in other areas now. But, I still feel like I look too trendy when I wear the jean tucked into boots look. I love the look on other people, but it feels like I'm "trying too hard" on me as a MOTG. Skinnies and ankle boots, yeah, I can wear that no problem or skinnies and just about any other shoe.

Actually, I think it may be tall boots in general because I feel strange in them with dresses too. Maybe I haven't found the right boots that are casual enough? I am ok with wearing wellies tucked in on rainy days, because it seems practical or snow boots tucked for the same reason. I guess it feels like jeans tucked into tall boots just screams..."look at me and my fashion!" when I'm wearing it anyway. I live in a very, very practical, rural area, so a lot of it is environmental challenges.

Maybe I should give up on it and wear the many other cutie shoes and booties? Do you have a particular "look" that you really like, but can't quite get comfortable with?

Dressing

21 replies

Latest reply was from lynn

Lynne

Veteran

Cilleena, just popping in to say fantastice to 'see' you back! Looking forward to catching up with all your news.....I'll leave it to others to comment on what might be happening with the tucking into tall boots.

Janet

(website)

Veteran

I like a lot of looks with leggings on other people but am not comfortable with the look on myself, so I understand the phenomenon.

I did just pick up a pair of black ponte jean leggings at Nordstrom Rack the other day, so we'll see if I manage to work them into some outfits or whether they end up going back!

Wearing jeans tucked into boots was the thing that finally nudged me into my first pair of skinnies (well, since college, at least). I always felt it was a shame to cover up the cute boots I had with boot cuts all the time. It took a little getting used to, but my eye adjusted.

Maybe post a pic of the boots in question?

JennyAnne

(website)

Veteran

I felt the same way for a long time. I'm in the boat that doesn't get on board with a trend until it's usually mainstream (or passe!). I've been wearing the jeans in boots for a while now, and I've found I'm most comfortable in flat, brown boots, which seem most casual and "practical" to me, as a fellow MOTG.

Irene

Veteran

Flat riding boots maybe? I tuck jeans into them all the time, it's actually my on-the-go look in winter. And I'm 23 and super casual, so I don't think it's like too fashionable or something like that.

Kristen

(website)

Veteran

I can't stand the look on myself, but I love it on others. For me, it's not about feeling like I am trying too hard with fashion, it's that it just isn't very flattering. My calves are my best asset, and covering them up with both jeans and boots so they are nearly the same width as my thighs doesn't do me any favors.
I've stopped worrying about it, and I enjoy the look on others. Instead, I stick with cute booties or fun wedges or shoes with my jeans.

nancylee

Veteran

As a skinnies holdout (I just bought my first pairs last month), I can relate to this to some extent. I live in a college town, and practically every coed sports the jeans/leggings tucked into boots look. I feel a little "old" wearing it compared to them....but I have to say I'm adjusting very quickly!

I think if you find a flat/low heel boot in a darker low-key color (one that doesn't contrast much with your jeans) you'll feel more comfortable.

Isis

Veteran

Cileena, Thanks for posting this. I feel EXACTLY the same way; I feel totally wierd with jeans tucked into boots, AND dresses with boots, like I'm screaming "trying too hard!!!!!"

So, no words of advice, just some commiseration! And I'm glad to know I'm not the only one who feels like this!

Suz

(website)

Veteran

Echoing Janet; for me, the problem is leggings. Love the look on others but feel like it doesn't work for me. However, I'll continue to experiment.

I'm wearing jeans tucked into boots and actually find it super practical and non-fashion-statement-like. Then again, I live in a college town where everybody walks around looking like this. Like Nancylee, I have my moments of feeling "old" compared to the students, but mostly I figure I blend in.

For me, flat boots are a necessity. I couldn't do it with heeled boots. So mine are a riding boot style that actually are my dressy winter boots!

lynne

Veteran

So glad to hear I'm not the only one. I tried it for the first time last winter and while I did feel like I was trying too hard, no one pointed and laughed (that I saw). I'm about to break the combo out again for this season. Take a deep breath and jump, ladies!

Queen Mum

Veteran

I'm no help, because it's become such my go-to look that I almost feel "so last year" in this silhouette. But if you can't feel comfortable in it, then yes, stick to your booties and other shoes that make you feel good.

cheryle (Dianthus)

(website)

Veteran

I live in a colder climate and wear boots with almost everything. I was more inclined to wear them with skirts/dresses but have been tucking in pants too since last winter. I find it is so much easier to not have to worry about changing to shoes when I get where I am going and not having to worry about getting snow on my tights or pants. Perhaps I have adopted the look more for practical reasons but I am now loving boots and have many pairs. I agree that a flat pair in a riding or moto style is the way to go for a casual look. If you decide to give it a try, perhaps an inexpensive pair of boots would be a good way to test it out. If you decide this isn't a look for you, then it is not much of a loss.

Scarlet

Veteran

Well, I don't feel this way at all. Tucking jeans into boots is so practical for me when it is rainy because I am on foot quite a bit. It saves my pants getting wet and dirty, and I can wipe off my boots. It is a very common look, though, where I live, so I don't think anyone thinks twice about it on me. It's not really clear to me from what you wrote whether this is a look you even like though. I wouldn't feel pressured to sport it unless you like it, and if you do, I would advise not caring about looking too fashion-y. In terms of do I ever feel this way myself, probably, but no particular look is jumping to mind right now.

Cilleena

Veteran

Scarlet, good point on whether I actually like the look. I DO like the look, but I think it has to be done a certain way. One day I saw a woman walk into the grocery store wearing tight jeans tucked into high heel boots and a shorter, waist length sweater. It looked really odd to me.
Dianthus-yes, it is practical. I also live in a colder climate and when the snow flies, I will be living in my skinnies and snow boots. I don't feel odd wearing that at all. But, snow boots are practical and very gear-like.

This is the look that would leave me feeling like I'm trying too hard. But, I think it's so cool looking.
http://goodlifeforless.blogspo.....again.html

When other moms dress up like this in my area, they are wearing bootcuts and flats or ankle boots.

I think maybe I'm just not a trend setter and in my area, it's still a trendy look. Maybe this is the year that it will become more mainstream. I did see one mom wearing boots tucked in at a Halloween party last night.

Freckles

Veteran

I really like the look and I see many older women sporting it here so the young vibe of it that others speak of doesn't hit me. I don't wear it myself, even though I love it, not sure why. I am more of a straight leg pants and ankle boots person.

I should sport it though as walking to chalk talks on wet wintry days the bottom of my pants do get wet...

sarah

Veteran

I felt similarly to you as well. But now I couldn't live without this look. My first foray into it was with straight/skinny jeans, a BF cardi, a tee, and a scarf. VERY casual and understated on top.

Scarlet

Veteran

Cileena, I realized I had never seen a WIW from you and just checked. I think your outfit here would work really well tucked into boots:
http://youlookfab.com/welookfa.....nd-booties

It's really not a trendy look in my book. It is classic, practical and stylish. Although it does have to be done right in terms of well-fitting boots and good leg proportions.

ETA: I found another picture with your face--of course I have seen you before It has been awhile though. Anyway, the point is, there is really nothing standing between you and you looking fab in knee-high boots except whether you feel comfortable. I would just focus on how much it appeals to you or not. I used to find it really hard to wear dresses to work because it is so outside of the environmental norm, but now I don't think twice about it. Feels so much better that way.
This would look great tucked too:
http://youlookfab.com/welookfa.....ckettake-2

Anonymous

I think tall boots and tucked jeans is actually a very practical look for cold, damp weather. I had an "aha" moment the first time I tried it...my feet and legs stayed dry and cozy all day. Maybe you just need to find the right pair of boots? I think something flat and low contrast against your jeans would be a good start.

I find the first couple times I try a new style I may feel a little self-conscious, but it wears off quickly

However, in my opinion skinnies with booties is just as fun and fashion forward. I think you could stick with that if you feel more comfortable!

sarah

Veteran

Oh, Scarlet rocks. Those are GREAT suggestions!

Angie

(website)

Fashion Stylist

Cilleena, over thinking this *extremely* practical look in this way can be thought of as "trying too hard". Food for thought

Ralph Lauren has been showing this vibe since the '70s. It's a classic.

Perhaps you don't have boots that feel casual enough?

Cilleena

Veteran

Thanks everyone. I think I needed a little YLF reassurance. I DO think that I need more casual boots. Probably some riding boots with a rubber tread on the bottom would do well. I have a pair of tall boots, but they "click" on the hard wood floors too much and they have a little wedge heel that feels slightly unstable to me, so they don't get worn a lot. Maybe I was mistaking that aversion with being afraid of the "look".

lynn

Veteran

The boots in your example have heels and I would feel uncomfortable in that too for a casual look. I like the idea of flat riding boots and very casual ones will make you feel less like you are trying too hard. Maybe even lug soles and a little worn finish. Good luck!