I hear that, with dark breeches, black boots and my black Airowear XC vest, my DH says I look like a SWAT team member 
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I’ll agree with this statement. Skintight clothing generally tends to look “prettiest” on someone with the Ideal Rider Body, although can still make a person look “put together” even without said IRB.
And I’m saying that as someone who most definitely doesn’t have an IRB 
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You and @MissusS apparently don’t live somewhere with a cold winter! Gloves all the time are necessary.
That said I will admit to the glove off for a specific activity (usually the one that’s going to get my glove(s) wet - I can dry off and put the still dry gloves back on) but I also keep multiple pairs/types of gloves that get switched out for various activities. Gloves tend to be the first thing “forgotten” in the spring and the cold, wet, mud cycle is very hard on my skin.
As far as looking put together there are little things that can help. If you’re going untucked, be untucked and not half tucked. When wearing layers keep inner layers shorter than outer layers. A shirt hem hanging out below a vest or jacket looks very untidy.
Smooth finish half (or full) chaps will collect less dirt and look better longer than suede finished chaps. That goes for the rest of your wardrobe too. Pay attention to clothing materials and the season. For example fleece in shedding or mud season creates an instant Pig Pen look with no effort. A slicker material will collect less dirt and brush off more easily. Dark breech colours like black look dusty very quickly in mud/dust season depending on the material.
One thing that drives me crazy is the sunblock, dirt, fly repellent, sunblock, dirt, fly repellent layers that accumulated on my arms when I was doing multiple horses/hours at the barn in the summer. It feels nasty to me as well as looking filthy, so I wear UV blocking sleeves.
Keeping a small towel in my grooming kit for my hands helps keep dirt off my clothes. Using a spray bottle to mist my horse reduces the dust and hair transfer to my clothing.
I do think the cut and fit of your clothes has the biggest impact. If they flatter your body then you’re going to look put together even if you’re dirty.
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I’m tall, quite muscular, and have no waist, and the Hadley Curvy breeches from SmartPak are the best-fitting pair I have found. Their talls are not joking around, either. I have a 31" inseam and they’re the first pair of breeches where I have ever returned the tall length for a standard. The Romfh Sarafina is OK on me, but too expensive to just be OK.
While riding alongside the road one day, I got stopped by a lady driving a Mercedes who told me that I looked like Jackie Kennedy and should be on the cover of Vogue. Now, my horse absolutely should be a cover model and I assume she was talking about him, but I was just wearing dark gray breeches and a striped mesh shirt. So maybe try that.
Oh gosh, the number of times I have taken off my belt and used it to catch a loose horse… I always wear one at the barn. (That, and my cell phone holster clips onto it.)
My best chance at looking put together after I leave the barn comes if I wash my face in the bathroom and my hair in the wash rack. Can’t help you there.
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Note to self:
When you finally get your first pair of trendy riding tights, don’t wear them to the barn inside out.
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For many years I wore a stirrup leather for a belt.
It was very useful for so much in a pinch, catch a horse, as a lead rope when one was missing, to secure a broken fence, stall door or gate in the moment, very handy all around.
My phone holder is a small, phone sized neoprene bag.
It has a carabiner that hangs from a belt loop, not the belt.
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I found a genre of fleece hoodie that is synthetic, it’s fleeced on the inside and smooth on the outside. The ones I bought (from Winners) are nicely cut and appropriate dark colors for me, and have turned out to last forever. They do warmth without picking up hay.
As far as belts, I think because I wear a fanny pack with its own belt, I don’t have room for a proper belt as well.
small waist, normal sized butt = belt in most styles of pants. sigh but at least I found some great elastic belts. I’ll never wear a “normal” one again.
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That’s so interesting! Because I always thought the “curvy” sizes were for well, curvy people whose waist was tiny compared to their hips. But I trust your judgement so may try a pair. The regular Hadley’s definitely didn’t fit me right!
Any you can link to?
I get them for 10 euros apiece at the outdoor markets in France, so no link, sorry!
LOL I live in Saskatchewan where it gets to some of the coldest temperatures on earth! I am very lucky to ride in an indoor, heated arena. It’s not piping hot but the temperature inside is around 0, even when it’s -40 outside. I tend to start with winter gloves on (to catch the horse, bring it in, get settled) but quickly warm up enough while grooming to take them off. Anything warmer than -10 most days feels downright balmy in the dead of winter here!
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I am shaped like a 2x4. If I don’t have a belt on I spend more time hiking my pants up than doing anything else!
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I like to use the noble equestrian or heritage breathable synthetic gloves for both grooming and riding. Adjustable and fun colors, washable as well.
To the OP- clothes don’t have to be pricey, but clean and well- fitting make a huge difference! If you don’t have a good tack store near you, find an online retailer with a good return policy and try some at home.
Try to use your riding clothes for just riding. If you have to re-paint fences or do other barn chore, do it in jeans and change into your riding gear when it’s time to ride. Never do chores in your riding boots - use clogs or sneakers or rain boots.
I had s trainer who would wear a utility apron (just imagine an apron with lots of pockets) when she wasn’t in the saddle. Kept her outfits clean, and she never had to look for her phone, or a brush or hoof pick. Pretty smart.
I like to use a tinted sunscreen and some waterproof mascara. It’s low- key and doesn’t require re-application. Baseball caps are a lifesaver as well.
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romfh! I’ve never had a breech flatter me the way they do - I think I have the champions and they are chef’s kiss
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Wisconsin in an indoor arena - I’ll put on a short sleeve workout shirt, heat zone long sleeve shirt, and a 1/4 zip winter weight pull over. Sometimes I have a down vest on too. I start my ride with a winter riding jacket or down coat and then end up getting warm when we start working. As long as I can keep my hands and face warm, I don’t usually get too cold.
I have several issues with “staying put together”. First is I own a grey horse - thorough cleaning required every time! Any dark breeches then collect white hair. I still prefer dark because it’s easier to hide stains.
Second is my head and hair. Large head (7 5/8 US helmet size) plus wavy/curly hair. Most of the time I can’t be bothered with pony tails. Baseball hats are either too small or look strange over poofy 80s hair I can’t control. I only wear a pony tail when it’s really hot. I get curls out the sides with a pony tail regardless of how long I keep the sides . That being said, if I’m stopping somewhere on the way home or want to look more presentable, I’ll redo my pony tail so there’s LESS curls sticking out.
I also love baby wipes to clean faces, hands, etc.
I wear gloves to groom. I just use my old worn out gloves for grooming - I always have a pair or two with holes that are still serviceably sound. For the really gross stuff, I have a box of nitrile gloves in my trunk just in case.
Boots clean and face clean go a long way to make you look more presentable. 
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I love Buckwild breeches! I have a 34" inseam, and these fit great! They don’t come all the way down to the tops of my paddock boots, but they are much better than most breeches I have found
Also, as far as sunshirts go, I have not found riding shirts that have long enough sleeves for me. I buy from Land’s End or Old Navy. Both have women’s tall shirts online (only). You could try for a men’s shirt but they might not fit correctly.
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Or with a pair of underwear working their way out of the bottom of one pants leg from the dryer!
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Most everything has been said already but I feel most put together when wearing clean tall boots, breeches, belt, tucked in shirt (sun shirt or polo something with a collar), hair braided, and gloves
How to not get dirty or sweaty? That I still have no idea 
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